Aza bicyclic (thio) amides as fungicidal compounds

Abstract

The present invention relates to azabicyclic (thio)amide compounds and their use for controlling phytopathogenic microorganisms (such as phytopathogenic fungi). The present invention also relates to methods and intermediates for preparing these compounds.

Description

[0001] The present invention relates to azabicyclic (thio)amide compounds and their use for controlling phytopathogenic microorganisms, such as phytopathogenic fungi. The present invention also relates to methods and intermediates for preparing these compounds.

[0002] To date, many crop protection agents have been developed for preventing or protecting against microbial infestation. However, there is still a need to develop new compounds that provide compounds effective against a broad spectrum of phytopathogenic microorganisms, such as fungi, which have low toxicity, high selectivity, or can be used at low application rates while still being effective against pests. There is also a desire for new compounds to prevent the emergence of resistance.

[0003] The present invention provides new compounds for controlling phytopathogenic microorganisms, such as fungi, which are superior to known compounds and compositions in at least some of these respects.

[0004] WO 2020 / 109391 discloses pyridazine amides as fungicides.

[0005] The present invention relates to compounds of formula (I):

[0006]

[0007] wherein

[0008] T is O or S,

[0009] n is 0 or 1,

[0010] m is 0 or 1,

[0011] A is N or CR 8 ,

[0012] wherein

[0013] R 8 is hydrogen, halogen, cyano or C1-C4-alkyl,

[0014] R 1 is hydrogen, hydroxy, cyano, C1-C6-alkyl, C1-C6-alkoxy, -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 , -S(=O)2R 12 , -C(=O)N(R 13 ), 2 or

[0015] -S(=O)2N(R 14 ), 2,

[0016] wherein

[0017] R10 , R 11 and R 12 are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[0018] R 13 and R 14 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[0019] R 2 and R 3 are independently hydrogen, halogen, cyano, hydroxy, carboxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl or C3-C8-cycloalkyl,

[0020] or

[0021] R 2 and R 3 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring or a 3- to 7-membered heterocyclic-ring,

[0022] R 4 and R 5 are independently hydrogen, halogen, cyano, hydroxy, carboxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl or C3-C8-cycloalkyl,

[0023] or

[0024] R 4 and R 5 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring or a 3- to 7-membered heterocyclic-ring,

[0025] or

[0026] R 2 and R 4 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring or a 3- to 7-membered heterocyclic-ring,

[0027] and

[0028] R 3 and R 5 are independently hydrogen or halogen,

[0029] or

[0030] R 2 and R 4 together form the formula **-C(R 3 )=C(R5 )- ## group

[0031] wherein

[0032] ** is the point connected to N(R 1 ).

[0033] ## is the point connected to R 6 .

[0034] and

[0035] R 3 and R 5 are independently hydrogen, halogen or C1-C6-alkyl,

[0036] R 6 is C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclic oxy group, C6-C 14 -aryloxy group, 5- to 14-membered heteroaryloxy group, 3- to 14-membered heterocyclic oxy group, C1-C3-alkoxy group or C1-C3-haloalkoxy group,

[0037] wherein the C1-C3-alkoxy group and the C1-C3-haloalkoxy group are independently substituted by a substituent selected from the following: C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl,

[0038] wherein the C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group

[0039] and 5- to 14-membered heteroaryl are each optionally substituted by 1 to 4 R 6S substituents, wherein the C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclic oxy group, C6-C 14 -aryloxy group, 5- to 14-membered heteroaryloxy group and 3- to 14-membered heterocyclic oxy group are optionally substituted by 1 to 4 R 6S substituents,

[0040] wherein

[0041] R 6SIndependently selected from halogen, cyano, isocyano, nitro, hydroxy, oxo, mercapto, pentafluorothio, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 15 )2, -C(=O)R 16 , -C(=O)(OR 17 ), -C(=O)N(R 18 )2, -S(=O)2N(R 19 )2, -O-Si(C1-C6-alkyl)3 or –Si(C1-C6-alkyl)3,

[0042] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and –Si(C1-C6-alkyl)3 are further optionally substituted by 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group,

[0043] and

[0044] wherein the C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14-aryl, 5- or 6-membered heteroaryl, and 3- to 7-membered heterocyclic group are further optionally substituted by 1 to 4 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl,

[0045] or

[0046] two C1-C6-alkyl substituents attached to the same carbon atom form a C3-C8-cycloalkyl-ring,

[0047] or

[0048] two R 6S substituents optionally together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0049] and, wherein

[0050] R 15 is independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl,

[0051] wherein, the C1-C6-alkyl is further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclic group,

[0052] and

[0053] wherein, the C3-C8-cycloalkyl is further optionally substituted by 1 to 4 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl,

[0054] R 16 、R 17 、R 18 and R 19 are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl,

[0055] Wherein, the C1-C6-alkyl or C1-C6-haloalkyl is further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group,

[0056] Ring Y together with the pyridine ring or pyridazine ring respectively forms a bicyclic heterocyclic group or bicyclic heteroaryl group,

[0057] p is 0, 1, 2, 3 or 4,

[0058] R 7 is halogen, cyano, nitro, hydroxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2,

[0059] Wherein, the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by 1 to 3 substituents independently selected from the following:

[0060] cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl, wherein the C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0061] and, wherein

[0062] R 20 is independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0063] wherein the C1-C6-alkyl is optionally substituted with 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0064] and

[0065] wherein the C3-C8-cycloalkyl is optionally substituted with 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0066] R 21 、R 22 、R 23 and R 24 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0067] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted with 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0068] Alternatively, wherein

[0069] two substituents R 7 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0070] Q is C6-C 14 -aryl, C3-C 12 -carbocyclic group, a 3- to 14-membered heterocyclic group or a 5- to 14-membered heteroaryl group,

[0071] wherein the C6-C 14 -aryl, C3-C 12 -carbocyclic group, a 3- to 14-membered heterocyclic group and a 5- to 14-membered heteroaryl group are optionally substituted by 1 to 5 independently selected from the following Q S substituents: halogen, cyano, isocyano, nitro, hydroxy, mercapto, formyl, carboxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, a 3- to 7-membered heterocyclic group, a 5- to 14-membered heteroaryl group, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, -O-C(=O)R 25 、-NR 26 C(=O)R 27 、-C(=O)N(R 28 )2、-C(=S)R 29 、-C(=S)N(R 30 )2、-C(=NR 31 )R 32 、-C(=NOR 33 )R 34 and -N(R 35 )2,

[0072] wherein

[0073] The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and –Si(C1-C6-alkyl)3 are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0074] The C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclic group and 5- to 14-membered heteroaryl are optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic group,

[0075] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are each optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0076] R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 and R 34 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0077] wherein

[0078] The C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0079] and, wherein

[0080] R 35 is independently hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl, wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0081] wherein the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic group, wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are optionally substituted in turn by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0082] and its N-oxides, salts, solvates and solvates of its salts and N-oxides.

[0083] The present invention relates to a composition comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable adjuvant.

[0084] The present invention also relates to the use of a compound of formula (I) as defined herein or a composition as defined herein for controlling phytopathogenic fungi.

[0085] The present invention relates to a method for controlling phytopathogenic fungi, which method comprises the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to a plant, a plant part, a seed, a fruit or to the soil in which the plant grows.

[0086] The present invention also relates to methods and intermediates for preparing the compounds of formula (I).

[0087] Unless otherwise stated, the following definitions apply to the substituents and residues used in this specification and the claims.

[0088] The term "halogen" as used herein refers to a fluorine, chlorine, bromine or iodine atom.

[0089] The term "methylene" as used herein refers to a CH2 group in which the carbon atoms are connected by a double bond.

[0090] The term "halomethylene" as used herein refers to a CX2 group in which the carbon atoms are connected by a double bond, where X is halogen.

[0091] The term "oxo" as used herein refers to an oxygen atom which is bonded to a carbon atom or a sulfur atom by a double bond.

[0092] The term "C1-C6-alkyl" as used herein refers to a branched or straight-chain saturated hydrocarbon chain having 1, 2, 3, 4, 5 or 6 carbon atoms. Examples of C1-C6-alkyl include, but are not limited to, methyl, ethyl, propyl (n-propyl), 1-methylethyl (isopropyl), butyl (n-butyl), 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. In particular, the hydrocarbon chain has 1, 2, 3 or 4 carbon atoms ("C1-C4-alkyl"), such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl or tert-butyl.

[0093] As used herein, the terms "C3-C8-cycloalkyl" and "C3-C8-cycloalkyl-ring" refer to monocyclic saturated hydrocarbon rings containing 3, 4, 5, 6, 7 or 8 carbon atoms. Examples of C3-C8-cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. In particular, the cycloalkyl has 3 to 6 carbon atoms.

[0094] As used herein, the term "C3-C8-halocycloalkyl" refers to one or more hydrogen atoms in the C3-C8-cycloalkyl as defined above being replaced by one or more halogen atoms, which may be the same or different.

[0095] As used herein, the term "C2-C6 alkenyl" refers to a branched or straight-chain unsaturated hydrocarbon chain having 2, 3, 4, 5 or 6 carbon atoms and containing at least one double bond. Examples of C2-C6 alkenyl include, but are not limited to, vinyl (or "ethenyl"), prop-2-en-1-yl (or "allyl"), prop-1-en-1-yl, but-3-enyl, but-2-enyl, but-1-enyl, pent-4-enyl, pent-3-enyl, pent-2-enyl, pent-1-enyl, hex-5-enyl, hex-4-enyl, hex-3-enyl, hex-2-enyl, hex-1-enyl, prop-1-en-2-yl (or "isopropenyl"), 2-methylprop-2-enyl, 1-methylprop-2-enyl, 2-methylprop-1-enyl, 1-methylprop-1-enyl, 3-methylbut-3-enyl, 2-methylbut-3-enyl, 1-methylbut-3-enyl, 3-methylbut-2-enyl, 2-methylbut-2-enyl, 1-methylbut-2-enyl, 3-methylbut-1-enyl, 2-methylbut-1-enyl, 1-methylbut-1-enyl, 1,1-dimethylprop-2-enyl, 1-ethylprop-1-enyl, 1-propylvinyl, 1-isopropylvinyl, 4-methylpent-4-enyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl, 1-methylpent-4-enyl, 4-methylpent-3-enyl, 3-methylpent-3-enyl, 2-methylpent-3-enyl, 1-methylpent-3-enyl, 4-methylpent-2-enyl, 3-methylpent-2-enyl, 2-methylpent-2-enyl, 1-methylpent-2-enyl, 4-methylpent-1-enyl, 3-methylpent-1-enyl, 2-methylpent-1-enyl, 1-methylpent-1-enyl, 3-ethylbut-3-enyl, 2-ethylbut-3-enyl, 1-ethylbut-3-enyl, 3-ethylbut-2-enyl, 2-ethylbut-2-enyl, 1-ethylbut-2-enyl, 3-ethylbut-1-enyl, 2-ethylbut-1-enyl, 1-ethylbut-1-enyl, 2-propylprop-2-enyl, 1-propylprop-2-enyl, 2-isopropylprop-2-enyl, 1-isopropylprop-2-enyl, 2-propylprop-1-enyl, 1-propylprop-1-enyl, 2-isopropylprop-1-enyl, 1-isopropylprop-1-enyl, 3,3-dimethylprop-1-enyl, 1-(1,1-dimethylethyl)vinyl, buta-1,3-dienyl, penta-1,4-dienyl, hexa-1,5-dienyl or methylhexadienyl.

[0096] As used herein, the term "C2-C6-alkynyl" refers to a branched or straight-chain hydrocarbon chain having 2, 3, 4, 5 or 6 carbon atoms and containing at least one triple bond. Examples of C2-C6-alkynyl include, but are not limited to, ethynyl, prop-1-ynyl, prop-2-ynyl (or "propargyl"), but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 1-methylprop-2-ynyl, 2-methylbut-3-ynyl, 1-methylbut-3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl, 1-ethylprop-2-ynyl, 3-methylpent-4-ynyl, 2-methylpent-4-ynyl, 1-methyl-pent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl, 4-methylpent-2-ynyl, 1-methyl-pent-2-ynyl, 4-methylpent-1-ynyl, 3-methylpent-1-ynyl, 2-ethylbut-3-ynyl, 1-ethylbut-3-ynyl, 1-ethylbut-2-ynyl, 1-propylprop-2-ynyl, 1-isopropylprop-2-ynyl, 2,2-dimethylbut-3-ynyl, 1,1-dimethylbut-3-ynyl, 1,1-dimethylbut-2-ynyl or 3,3-dimethylbut-1-ynyl.

[0097] As used herein, the term "C1-C6-haloalkyl" refers to one or more hydrogen atoms in the C1-C6-alkyl as defined above being replaced by one or more halogen atoms, which halogen atoms may be the same or different. Examples of C1-C6-haloalkyl include, but are not limited to, chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoro-ethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl. Preferred are fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, 2-fluoroethyl, 2,2-difluoro-ethyl, 2,2,2-trifluoroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.

[0098] As used herein, the term "C1-C6-fluoroalkyl" refers to one or more hydrogen atoms in the C1-C6-alkyl as defined above being replaced by one or more fluorine atoms, which fluorine atoms may be the same or different. Examples of C1-C6-fluoroalkyl include, but are not limited to, monofluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl and 2,2,2-trifluoroethyl.

[0099] The term "C2-C6-haloalkenyl" as used herein means that one or more hydrogen atoms in the C2-C6-alkenyl as defined above are replaced by one or more halogen atoms, and the halogen atoms may be the same or different.

[0100] The term "C2-C6-haloalkynyl" as used herein means that one or more hydrogen atoms in the C2-C6-alkynyl as defined above are replaced by one or more halogen atoms, and the halogen atoms may be the same or different.

[0101] The term "C1-C6-alkoxy" as used herein means a group of the formula (C1-C6-alkyl)-O-, where the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methylpentyloxy, 4-methylpentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Unless otherwise defined, this definition also applies to alkoxy as part of a complex substituent, such as alkoxyalkyl, alkoxyalkoxy.

[0102] The term "C1-C6-haloalkoxy" as used herein means that one or more hydrogen atoms in the C1-C6-alkoxy as defined above are replaced by one or more halogen atoms, and the halogen atoms may be the same or different. Examples of C1-C6-haloalkoxy include, but are not limited to, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoropropan-2-oxy.

[0103] The term "C3-C8-cycloalkyloxy" as used herein refers to a monocyclic saturated cycloalkyloxy having 3 to 8, preferably 3 to 6, carbon ring members, such as (but not limited to) cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy. Unless otherwise defined, this definition also applies to cycloalkyloxy as part of a compound substituent, such as cycloalkyloxyalkyl.

[0104] The term "C2-C6-alkenyloxy" as used herein refers to the formula (C2-C6-alkenyl)-O-, where the term "C1-C6-alkenyl" group is as defined herein. Examples of C2-C6-alkenyloxy include, but are not limited to, vinyloxy (or "acetoxy"), prop-2-en-1-oxy (or "allyl"), prop-1-en-1-oxy, but-3-enyloxy, but-2-enyloxy, but-1-enyloxy, pent-4-enyloxy, pent-3-enyloxy, pent-2-enyloxy, pent-1-enyloxy, hex-5-enyloxy, hex-4-enyloxy, hex-3-enyloxy, hex-2-enyloxy, hex-1-enyloxy, prop-1-en-2-oxy (or "isopropenyloxy"), 2-methylprop-2-enyloxy, 1-methylprop-2-enyloxy, 2-methylprop-1-enyloxy, 1-methylprop-1-enyloxy, 3-methylbut-3-enyloxy, 2-methylbut-3-enyloxy, 1-methylbut-3-enyloxy, 3-methylbut-2-enyloxy, 2-methylbut-2-enyloxy, 1-methylbut-2-enyloxy, 3-methylbut-1-enyloxy, 2-methylbut-1-enyloxy, 1-methylbut-1-enyloxy, 1,1-dimethylprop-2-enyloxy, 1-ethylprop-1-enyloxy, 1-propylvinyloxy, 1-isopropylvinyloxy, 4-methylpent-4-enyloxy, 3-methylpent-4-enyloxy, 2-methylpent-4-enyloxy, 1-methylpent-4-enyloxy, 4-methylpent-3-enyloxy, 3-methylpent-3-enyloxy, 2-methylpent-3-enyloxy, 1-methylpent-3-enyloxy, 4-methylpent-2-enyloxy, 3-methylpent-2-enyloxy, 2-methylpent-2-enyloxy, 1-methylpent-2-enyloxy, 4-methylpent-1-enyloxy, 3-methylpent-1-enyloxy, 2-methylpent-1-enyloxy, 1-methylpent-1-enyloxy, 3-ethylbut-3-enyloxy, 2-ethylbut-3-enyloxy, 1-ethylbut-3-enyloxy, 3-ethylbut-2-enyloxy, 2-ethylbut-2-enyloxy, 1-ethylbut-2-enyloxy, 3-ethylbut-1-enyloxy, 2-ethylbut-1-enyloxy, 1-ethylbut-1-enyloxy, 2-propylprop-2-enyloxy, 1-propylprop-2-enyloxy, 2-isopropylprop-2-enyloxy, 1-isopropylprop-2-enyloxy, 2-propylprop-1-enyloxy, 1-propylprop-1-enyloxy, 2-isopropylprop-1-enyloxy, 1-isopropylprop-1-enyloxy, 3,3-dimethylprop-1-enyloxy, 1-(1,1-dimethylethyl)vinyloxy, buta-1,3-dienyloxy, penta-1,4-dienyloxy, hexa-1,5-dienyloxy or methylhexadienyloxy.

[0105] The term "C2-C6-haloalkenyloxy" as used herein means that one or more hydrogen atoms in the (C2-C6-alkenyl)-O-group defined above are replaced by one or more halogen atoms, and the halogen atoms may be the same or different.

[0106] The term "C1-C6-alkylthio" as used herein means a straight-chain or branched-chain saturated group of the formula (C1-C6-alkyl)-S-, wherein the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkylthio include, but are not limited to, methylthio, ethylthio, propylthio, isopropylthio, butylthio, sec-butylthio, isobutylthio, tert-butylthio, pentylthio, isopentylthio, hexylthio.

[0107] The term "C1-C6-haloalkylthio" as used herein means that one or more hydrogen atoms in the C1-C6-alkylthio defined above are replaced by one or more halogen atoms, and the halogen atoms may be the same or different.

[0108] The term "C3-C8-cycloalkylthio" as used herein means a monovalent, monocyclic saturated hydrocarbon ring containing 3, 4, 5, 6, 7 or 8 carbon atoms and bonded to the backbone through a sulfur atom. Examples of monocyclic C3-C8-cycloalkylthio include, but are not limited to, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cycloheptylthio or cyclooctylthio.

[0109] The term "C1-C6-alkylsulfinyl" as used herein refers to a straight-chain or branched-chain saturated group of the formula (C1-C6-alkyl)-S(=O)-, where the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkylsulfinyl include, but are not limited to, straight-chain or branched-chain saturated alkylsulfinyl groups having from 1 to 8, preferably from 1 to 6 and more preferably from 1 to 4 carbon atoms, such as (but not limited to) C1-C6-alkylsulfinyl, such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

[0110] The term "C1-C6-haloalkylsulfinyl" as used herein refers to a C1-C6-alkylsulfinyl group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different.

[0111] The term "C3-C8-cycloalkylsulfinyl" as used herein refers to a monovalent, monocyclic saturated hydrocarbon ring containing 3, 4, 5, 6, 7 or 8 carbon atoms and bonded to the backbone through an -S(=O)- group. Examples of monocyclic C3-C8-cycloalkylsulfinyl include, but are not limited to, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, cycloheptylsulfinyl or cyclooctylsulfinyl.

[0112] As used herein, the term "C1-C6-alkylsulfonyl" refers to a straight-chain or branched-chain saturated group of the formula (C1-C6-alkyl)-S(=O)2-, where the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkylsulfonyl include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl.

[0113] As used herein, the term "C1-C6-haloalkylsulfonyl" refers to one or more hydrogen atoms in the C1-C6-alkylsulfonyl as defined above being replaced by one or more halogen atoms, where the halogen atoms may be the same or different.

[0114] As used herein, the term "C3-C8-cycloalkylsulfonyl" refers to a monovalent, monocyclic saturated hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms and bonded to the backbone through an -S(=O)2- group. Examples of monocyclic C3-C8-cycloalkylsulfonyl include, but are not limited to, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cycloheptylsulfonyl, or cyclooctylsulfonyl.

[0115] As used herein, the term "C1-C6-alkylcarbonyl" refers to a straight-chain or branched-chain saturated group of the formula (C1-C6-alkyl)-C(=O)-, where the term "C1-C6-alkyl" is as defined herein.

[0116] As used herein, the term "C1-C6-haloalkylcarbonyl" refers to one or more hydrogen atoms in the C1-C6-alkylcarbonyl as defined above being replaced by one or more halogen atoms, where the halogen atoms may be the same or different.

[0117] As used herein, the term "C1-C6-alkoxycarbonyl" refers to a straight-chain or branched-chain saturated group of the formula (C1-C6-alkoxy)-C(=O)-, where the term "C1-C6-alkoxy" is as defined herein.

[0118] As used herein, the term "C1-C6-haloalkoxycarbonyl" refers to a group in which one or more hydrogen atoms in the C1-C6-alkoxycarbonyl as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0119] As used herein, the term "C3-C 12 -carbocyclic group" refers to a saturated or partially unsaturated hydrocarbon ring system in which all ring members (which may be 3 to 12) are carbon atoms. The ring system may be monocyclic or polycyclic (fused, spiro or bridged). C3-C 12 -carbocycles include but are not limited to C3-C 12 -cycloalkyl (monocyclic or bicyclic), C3-C 12 -cycloalkenyl (monocyclic or bicyclic), a bicyclic system comprising an aryl group (such as phenyl) fused to a monocyclic C3-C8-cycloalkyl (such as tetrahydronaphthyl, dihydroindenyl), a bicyclic system comprising an aryl group (such as phenyl) fused to a monocyclic C3-C8-cycloalkenyl (such as indenyl, dihydronaphthyl), and a tricyclic system comprising a cyclopropyl group linked to a bicyclic system through one carbon atom, the bicyclic system comprising an aryl group (such as phenyl) fused to a C3-C8-cycloalkyl or C3-C8-cycloalkenyl. The C3-C 12 -carbocycle may be linked to the parent molecular moiety through any carbon atom.

[0120] As used herein, the term "C3-C 12 -cycloalkenyl" refers to a monovalent, monocyclic or bicyclic unsaturated hydrocarbon ring containing 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms and 1 or 2 double bonds. Examples of monocyclic C3-C8-cycloalkenyl include but are not limited to cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl. Examples of bicyclic C6-C 12 -cycloalkenyl include but are not limited to bicyclo[2.2.1]hept-2-enyl or bicyclo[2.2.2]oct-2-enyl.

[0121] As used herein, the term "C6-C 14 -aryl" refers to an aromatic hydrocarbon ring system in which all ring members (which may be 6 to 14, preferably 6 to 10) are carbon atoms. The ring system may be monocyclic or fused polycyclic (such as bicyclic or tricyclic). Examples of aryl include but are not limited to phenyl, azulenyl and naphthyl.

[0122] As used herein, the term "3- to 14-membered heterocyclic group" refers to a 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13- or 14-membered saturated or partially unsaturated ring system containing 1 to 4 heteroatoms independently selected from oxygen, nitrogen and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent. Heterocycles include, but are not limited to, 3- to 7-membered monocyclic heterocycles and 8- to 14-membered polycyclic (such as bicyclic or tricyclic) heterocycles. The 3- to 14-membered heterocyclic group can be linked to the parent molecular moiety through any carbon atom or nitrogen atom contained in the heterocycle. Examples of saturated heterocycles include, but are not limited to, 3-membered rings such as oxiranyl, aziridinyl; 4-membered rings such as azetidinyl, oxetanyl, thietanyl; 5-membered rings such as tetrahydrofuryl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl; 6-membered rings such as piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothiopyranyl, dithianyl, morpholinyl, 1,2-oxazepanyl, oxathiazepanyl, thiomorpholinyl; or 7-membered rings such as oxepanyl, azepanyl, 1,4-diazepanyl and 1,4-oxazepanyl. Examples of unsaturated heterocyclic groups include, but are not limited to, 5-membered rings such as dihydrofuryl, 1,3-dioxoleneyl, dihydrothienyl, pyrrolineyl, dihydroimidazolyl, dihydropyrazolyl, isoxazolineyl, dihydrooxazolyl, dihydrothiazolyl; or 6-membered rings such as pyranyl, thiopyranyl, thiazinyl and thiadiazinyl. The bicyclic heterocycle can be composed of a monocyclic heteroaryl as defined herein fused to a monocyclic C3-C8-cycloalkyl, monocyclic C3-C8-cycloalkenyl or monocyclic heterocycle, or can be composed of a monocyclic heterocycle fused to an aryl (such as phenyl), C3-C8-cycloalkyl, C3-C8-cycloalkenyl or monocyclic heterocycle (for example, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, benzodihydropyranyl, isobenzodihydropyranyl, thio-benzodihydropyranyl and isothio-benzodihydropyranyl). When two monocyclic heterocycles or a monocyclic heterocycle and a monocyclic heteroaryl containing a nitrogen atom are fused, the nitrogen atom can be located at the bridging position (for example, [1,3]dioxoleno[4,5-b]pyridinyl, 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydroimidazo[1,2-a]pyridinyl).The tricyclic heterocycle can be composed of a monocyclic aryl group that connects a bicyclic heterocycle through a shared atom.

[0123] As used herein, the terms "3- to 7-membered heterocyclic group" and "3- to 7-membered heterocyclic ring" refer to a 3-, 4-, 5-, 6- or 7-membered saturated ring system containing 1 or 2 heteroatoms independently selected from oxygen, nitrogen and sulfur. Examples include, but are not limited to, oxiranyl, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuryl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazacyclohexyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothianyl, dithianyl, morpholinyl, 1,2-oxazacyclohexyl, oxathiazacyclohexyl, thiomorpholinyl, oxepanyl, azepanyl, 1,4-diazepanyl and 1,4-oxazepanyl. Preferred 3- to 7-membered heterocyclic groups are oxiranyl, aziridinyl, azetidinyl, oxetanyl, tetrahydrofuryl, 1,3-dioxolanyl, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxanyl, morpholinyl and thiomorpholinyl.

[0124] As used herein, the term "5- to 14-membered heteroaryl" refers to an aromatic ring system containing 1 to 4 heteroatoms independently selected from oxygen, nitrogen and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent. Aromatic heterocycles include 5- or 6-membered monocyclic heteroaryls and 7- to 14-membered polycyclic (such as bicyclic or tricyclic) heteroaryls. The 5- to 14-membered heteroaryl can be linked to the parent molecular moiety through any carbon atom or nitrogen atom contained in the heterocycle.

[0125] As used herein, the term "5- or 6-membered heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring system containing 1, 2, 3 or 4 heteroatoms independently selected from oxygen, nitrogen and sulfur. Examples of 5-membered monocyclic heteroaryls include, but are not limited to, furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, isoxazolyl, oxazolyl, oxadiazolyl, oxatriazolyl, isothiazolyl, thiazolyl, thiadiazolyl and thiatriazolyl. Examples of 6-membered monocyclic heteroaryls include, but are not limited to, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl.

[0126] As used herein, the term "7- to 14-membered heteroaryl" refers to a 7-, 8-, 9-, 10-, 11-, 12-, 13- or 14-membered aromatic polycyclic (such as bicyclic or tricyclic) ring system containing 1, 2 or 3 heteroatoms independently selected from oxygen, nitrogen and sulfur. A bicyclic heteroaryl may be composed of a monocyclic heteroaryl as defined herein fused to an aryl (such as phenyl) or a monocyclic heteroaryl. Examples of bicyclic heteroaryls include, but are not limited to, 9-membered rings such as indolyl, indolizinyl, isoindolyl, benzimidazolyl, imidazopyridinyl, indazolyl, benzotriazolyl, purinyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl and benzisoxazolyl, or 10-membered rings such as quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, pteridinal and benzodioxinyl. In a 9- or 10-membered bicyclic heteroaryl containing two fused 5- or 6-membered monocyclic heteroaryls, the nitrogen atom may be located at the bridgehead (such as imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, imidazo[2,1-b]oxazolyl, furano[2,3-d]isoxazolyl). Examples of tricyclic aromatic heterocyclics include, but are not limited to, carbazolyl, acridinyl and phenazinyl.

[0127] The 5- to 8-membered carbocyclic group fused to a pyridine ring / pyridazine ring for Y as used herein refers to a 5-, 6-, 7- or 8-membered saturated or partially unsaturated ring fused to a pyridine ring or pyridazine ring, respectively. The 5- to 8-membered carbocyclic group fused to a pyridine ring / pyridazine ring for Y as used herein refers to a 5-, 6-, 7- or 8-membered saturated or partially unsaturated cyclic heterocycle containing 1, 2 or 3 heteroatoms or groups independently selected from N, O, S, SO or SO2 and fused to a pyridine ring or pyridazine ring, respectively. Examples of the resulting bicyclic ring systems include, but are not limited to, furano[3,2-b]pyridine, furano[3,2-c]pyridazine, thieno[2,3-b]pyridine, thieno[2,3-c]pyridazine, thieno[3,2-b]pyridine, thieno[3,2-c]pyridazine, pyrrolo[2,3-b]pyridine, 1H-pyrrolo[3,2-b]pyridine, 7H-pyrrolo[2,3-c]pyridazine, 5H-pyrrolo[3,2-c]pyridazine, thiazolo[5,4-b]pyridine, thiazolo[5,4-c]pyridazine, oxazolo[5,4-b]pyridine, oxazolo[5,4-c]pyridazine, oxazolo[4,5-b]pyridine, oxazolo[4,5-c]pyridazine, thiazolo[4,5-b]pyridine, thiazolo[4,5-c]pyridazine, 1H-imidazo[4,5-b]pyridine, 5H-imidazo[4,5-c]pyridazine, 3H-imidazo[4,5-b]pyridine, 7H-imidazo[4,5-c]pyridazine, 1,5-naphthyridine, pyrido[3,2-c]pyridazine, pyrido[2,3-c]pyridazine, pyridazino[3,4-c]pyridazine, pyridazino[4,3-c]pyridazine, quinoline, cinnoline, pyrido[3,2-d]pyrimidine, pyrimido[5,4-c]pyridazine, pyrido[3,4-c]pyridazine, pyrido[2,3-b]pyrazine, tetrahydroquinoline, tetrahydrocinnoline, dihydro-5H-cyclopentano[c]pyridazine, dihydro-5H-cyclopentano[c]pyridine, 2,3-dihydro-[1,4]dioxino[2,3-b]pyridine, 6,7-dihydro-[1,4]dioxino[2,3-b]pyridazine, 7,8-dihydro-5H-pyrano[4,3-c]pyridazine, 5,6,7,8-tetrahydropyrido[3,2-c]pyridazine, 5,6,8,9-tetrahydrooxazolo[4,5-c]pyridazine, 7,8-dihydro-6H-[1,4]dioxino[2,3-c]pyridazine and 1,2,3,4-tetrahydro-1,5-naphthyridine.

[0128] The term “C3-C 12 -carbocyclyloxy”, “C3-C8-cycloalkyloxy”, “C6-C 14 -aryloxy”, “5- to 14-membered heteroaryloxy”, “3- to 14-membered heterocyclyloxy” as used herein refers to a group of the formula –O-R, where R is a C3-C 12 -carbocyclic group, C3-C8-cycloalkyl group, C6-C14 -aryl, 5- to 14-membered heteroaryl or 3- to 14-membered heterocyclic group.

[0129] As used herein, the term "leaving group" is understood to mean a group that is transferred from a compound in a substitution or elimination reaction, such as a halogen atom, a triflate group, an alkoxy group, a mesylate group, a tosylate group, etc.

[0130] When referring to the variables A, Y, Q, T, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、p, n and m, the term "as described herein" incorporates by reference the broad definitions of the variables, as well as the preferred, more preferred and even more preferred definitions (if any).

[0131] Compounds obtained by combinations that are contrary to the laws of nature and that would thus be excluded by a person skilled in the art based on his / her expertise are not covered herein. For example, a ring structure having three or more adjacent oxygen atoms is excluded.

[0132] The compounds of formula (I) may suitably be in their free form, salt form, N-oxide form or solvate form (e.g., hydrate).

[0133] Depending on the nature of the substituents, the compounds of formula (I) may exist in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the present invention encompasses pure stereoisomers and any mixtures of these isomers. When a compound can exist in more than two tautomeric forms in equilibrium, the compound referred to by means of one tautomeric description is to be considered as including all tautomeric forms.

[0134] Depending on the number of double bonds in the compound, any compound of the present invention may also exist in the form of one or more geometric isomers. Depending on the nature of the substituents on the double bond or the ring, the geometric isomers may exist in the cis (=Z-) or trans (=E-) form. Accordingly, the present invention equally relates to all geometric isomers and all possible mixtures in all ratios.

[0135] Depending on the nature of the substituents, the compounds of formula (I) may exist in the form of the free compound and / or its salts (such as agrochemically active salts).

[0136] Agrochemically active salts include acid addition salts of inorganic and organic acids and salts of conventional bases. Examples of inorganic acids are hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, sulfuric acid, phosphoric acid and nitric acid, as well as acid salts such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono-unsaturated or di-unsaturated fatty acids having 6 to 20 carbon atoms, alkyl sulfate monoesters, alkylsulfonic acids (sulfonic acids having straight-chain or branched-chain alkyl groups with 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic groups such as phenyl and naphthyl with one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched-chain alkyl groups with 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic groups such as phenyl and naphthyl with one or two phosphonic acid groups), where the alkyl and aryl groups may carry other substituents such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

[0137] A solvate of a compound or its salt of the present invention is a stoichiometric composition of the compound with a solvent.

[0138] The compounds of the present invention can exist in a variety of crystalline and / or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates and hydrates.

[0139] The present invention also relates to methods and intermediates for preparing the compounds of formula (I).

[0140] When referring to the variables A, R 1 、R 2 、R 3 、R、R 45 、R、R 67 、R 8 、T, Y, n, m, p and Q, the term "as described herein" incorporates by reference the broad definitions of the said variables and the preferred, more preferred and even more preferred definitions (if any).

[0141] Similarly, the present invention relates to compounds of formula (I) wherein

[0142] T is O or S,

[0143] n is 0 or 1,

[0144] m is 0 or 1,

[0145] A is N or CR 8 ,

[0146] wherein

[0147] R8 is hydrogen or a halogen,

[0148] R 1 is hydrogen, a hydroxyl group, a cyano group, a C1-C6-alkyl group, a C1-C6-alkoxy group, -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 , -S(=O)2R 12 , -C(=O)N(R 13 )2 or -S(=O)2N(R 14 )2,

[0149] wherein

[0150] R 10 , R 11 and R 12 are independently a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C3-C8-cycloalkyl group or a C2-C6-alkenyl group,

[0151] R 13 and R 14 are independently hydrogen, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C3-C8-cycloalkyl group or a C2-C6-alkenyl group,

[0152] R 2 and R 3 are independently hydrogen, a halogen, a cyano group, a hydroxyl group, a carboxyl group, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C1-C6-alkoxy group, a C1-C6-alkoxycarbonyl group or a C3-C8-cycloalkyl group,

[0153] or

[0154] R 2 and R 3 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclic ring,

[0155] R 4 and R 5 are independently hydrogen, a halogen, a cyano group, a hydroxyl group, a carboxyl group, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C1-C6-alkoxy group, a C1-C6-alkoxycarbonyl group or a C3-C8-cycloalkyl group,

[0156] or

[0157] R 4 and R 5 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclic ring,

[0158] or

[0159] R 2 and R 4 together with the carbon atom(s) to which they are attached form a C3-C8-cycloalkyl-ring or a 3- to 7-membered heterocyclic-ring,

[0160] and

[0161] R 3 and R 5 are independently hydrogen or halogen,

[0162] or

[0163] R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## wherein

[0164] ** is the point of attachment to N(R

[0165] ) and 1

[0166] ## is the point of attachment to R 6 and

[0167]

[0168]

[0169] R 3 and R 5 are independently hydrogen or C1-C6-alkyl,

[0170] R 6 is C3-C 12 -carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclic oxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclic oxy, C1-C3-alkoxy or C1-C3-haloalkoxy,

[0170] wherein the C1-C3-alkoxy and C1-C3-haloalkoxy are independently substituted by a substituent selected from: C3-C 12 -carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic and 5- to 14-membered heteroaryl,

[0171] wherein the C3-C 12 -carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic and 5- to 14-membered heteroaryl are each optionally substituted by 1 to 4 R 6S substituents,

[0172] wherein, C3-C 12 -carbocyclic group, C6-C 14 -aryl group, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl group, C3-C 12 -carbocyclic oxy group, C6-C 14 -aryloxy group, 5- to 14-membered heteroaryloxy group, and 3- to 14-membered heterocyclic oxy group are optionally substituted with 1 to 4 R 6S substituents,

[0173] wherein

[0174] R 6S is halogen, cyano, isocyano, nitro, hydroxy, mercapto, pentafluorothio, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl group, 5- or 6-membered heteroaryl group, 3- to 7-membered heterocyclic group, -N(R 15 )2, -C(=O)R 16 , -C(=O)(OR 17 ), -C(=O)N(R 18 )2, -S(=O)2N(R 19 )2, -O-Si(C1-C6-alkyl)3 or –Si(C1-C6-alkyl)3,

[0175] Wherein, the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and –Si(C1-C6-alkyl)3 are further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group,

[0176] and

[0177] Wherein, the C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are further optionally substituted by 1 to 4 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0178] or

[0179] two substituents C1-C6-alkyl connected to the same carbon atom form a C3-C8-cycloalkyl-ring,

[0180] or

[0181] two R 6S substituents optionally form a C3-C8-cycloalkyl-ring together with the carbon atom to which they are attached,

[0182] and, wherein

[0183] R 15 is hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0184] wherein the C1-C6-alkyl is further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group,

[0185] and

[0186] wherein the C3-C8-cycloalkyl is further optionally substituted by 1 to 4 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0187] R 16 、R 17 、R 18 and R 19 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0188] wherein the C1-C6-alkyl or C1-C6-haloalkyl is further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group,

[0189] Ring Y together with the pyridine ring or pyridazine ring forms a bicyclic heterocyclic group or bicyclic heteroaryl,

[0190] p is 0, 1, 2, 3 or 4,

[0191] R 7 is halogen, cyano, nitro, hydroxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2,

[0192] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl, wherein C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted by 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0193] and, wherein

[0194] R 20 is independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0195] wherein C1-C6-alkyl is optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0196] and

[0197] Wherein, the C3-C8-cycloalkyl is optionally substituted with 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0198] R 21 、R 22 、R 23 and R 24 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0199] Wherein, the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted with 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0200] Or, wherein

[0201] two substituents R 7 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0202] Q is C6-C 14 -aryl, C3-C 12 -carbocyclic group, a 3- to 14-membered heterocyclic group or a 5- to 14-membered heteroaryl group,

[0203] Wherein, the C6-C 14 -aryl, C3-C 12 -carbocyclic group, a 3- to 14-membered heterocyclic group and a 5- to 14-membered heteroaryl group are optionally substituted with 1 to 5 substituents independently selected from the following Q SSubstituted by substituents: halogen, cyano, isocyano, nitro, hydroxy, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclic group, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, -O-C(=O)R 25 、-NR 26 C(=O)R 27 、-C(=O)N(R 28 )2、-C(=S)R 29 、-C(=S)N(R 30 )2、-C(=NR 31 )R 32 、-C(=NOR 33 )R 34 and -N(R 35 )2,

[0204] wherein

[0205] The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and –Si(C1-C6-alkyl)3 are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0206] The C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclic group and 5- to 14-membered heteroaryl are optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic group,

[0207] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are optionally substituted by two substituents in turn, and the two substituents together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0208] R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 and R 34 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0209] wherein

[0210] The C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy groups are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic groups,

[0211] and, wherein

[0212] R 35 is hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl, wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic groups,

[0213] wherein the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic groups,

[0214] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic groups are each optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0215] and its N-oxides, salts, solvates and solvates of its salts and N-oxides.

[0216] Preferably, the present invention relates to a compound of formula (I), wherein

[0217] T is O or S,

[0218] n is 0 or 1,

[0219] m is 0 or 1,

[0220] A is N or CR 8 ,

[0221] wherein

[0222] R 8 is hydrogen, fluorine, chlorine, methyl or ethyl,

[0223] R 1 is hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy or -C(=O)R 10 ,

[0224] wherein

[0225] R 10 is C1-C4-alkyl,

[0226] R 2 and R 3 are independently hydrogen, fluorine, chlorine or C1-C4-alkyl,

[0227] R 4 and R 5 are independently hydrogen, halogen, C1-C4-alkyl or C3-C6-cycloalkyl,

[0228] or

[0229] R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0230] or

[0231] R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## ,

[0232] wherein

[0233] ** is the point of attachment to N(R 1 ),

[0234] ## is the point of attachment to R 6 ,

[0235] and

[0236] R 3 and R 5 are independently hydrogen, fluorine or C1-C4-alkyl,

[0237] R 6 is C5-C10 -carbocyclic group, phenyl, naphthyl, 5- to 10-membered heterocyclic group, 5- to 10-membered heteroaryl group, C5-C 10 -carbocyclic group oxy, phenoxy, benzyloxy, 5- to 10-membered heteroaryl group oxy, 5- to 10-membered heterocyclic group oxy, C1-C3-alkoxy or C1-C3-haloalkoxy,

[0238] wherein the C1-C3-alkoxy and C1-C3-haloalkoxy are independently substituted by a substituent selected from the following: C5-C 10 -carbocyclic group, phenyl, naphthyl, 5- to 10-membered heterocyclic group and 5- to 10-membered heteroaryl group,

[0239] wherein the C5-C 10 -carbocyclic group, phenyl, naphthyl, 5- to 10-membered heterocyclic group and 5- to 10-membered heteroaryl group are each optionally substituted by 1 to 3 R 6S substituents,

[0240] wherein, C5-C 10 -carbocyclic group, phenyl, naphthyl, 5- to 10-membered heterocyclic group, 5- to 10-membered heteroaryl group, C5-C 10 -carbocyclic group oxy, phenoxy, naphthoxy, 5- to 10-membered heteroaryl group oxy and 5- to 10-membered heterocyclic group oxy are optionally substituted by 1 to 3 R 6S substituents,

[0241] wherein

[0242] R 6S is independently halogen, cyano, oxo, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, naphthyl, thiophenyl, pyrazolyl, imidazolyl, pyridyl, pyrimidinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R 16 or -C(=O)(OR 17 ),

[0243] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl and C2-C4-haloalkynyl are further optionally substituted by 1 to 2 substituents independently selected from the following: cyano, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, -O-Si(C1-C4-alkyl)3, –Si(C1-C4-alkyl)3 and C3-C6-cycloalkyl,

[0244] and

[0245] wherein the C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, naphthyl, thienyl, pyrazolyl, imidazolyl, pyridyl, pyrimidinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl and tetrahydropyranyl are further optionally substituted by 1 or 2 substituents independently selected from the group consisting of: halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C6-alkoxycarbonyl,

[0246] wherein

[0247] R 16 and R 17 are independently C1-C4-alkyl,

[0248] Ring Y together with the pyridine ring or the pyridazine ring forms a group of formula (II-a) to (II-aa),

[0249]

[0250]

[0251] wherein

[0252] * is the point of attachment to the group -O-Q,

[0253] # is the point of attachment to -N(R 1 )

[0254] G is O, S or NR 7L ,

[0255] wherein

[0256] R 7L is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl or C3-C8-cycloalkyl,

[0257] p is 0, 1, 2, 3 or 4,

[0258] x 1 is 1 or 2,

[0259] x 2 is 0, 1 or 2,

[0260] R 7A 、R 7B 、R 7C 、R 7D 、R 7E 、R 7F and R 7Gindependently is hydrogen, hydroxy, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C3-C8-cycloalkyl,

[0261] R 7H is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl,

[0262] R 7K is methylene, halomethylene, halogen, hydroxy, oxo, C1-C4-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl,

[0263] or

[0264] two substituents R 7K together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0265] Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxanyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furanopyridinyl, thienothiophenyl or thienothiazolyl, wherein phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxanyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furanopyridinyl, thienothiophenyl or thienothiazolyl are optionally substituted by 1 to 3 Qs independently selected from the following SSubstituted by a substituent: halogen, cyano, nitro, hydroxy, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxy-C1-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylthio, C1-C4-haloalkylthio, C3-C6-cycloalkyl, oxetanyl and -N(R 35 )2,

[0266] wherein

[0267] said C3-C6-cycloalkyl is optionally substituted by 1 or 2 substituents independently selected from: halogen, C1-C4-alkyl and C1-C4-haloalkyl,

[0268] and, wherein

[0269] R 35 is independently hydrogen or C1-C4-alkyl,

[0270] and its N-oxides, salts, solvates and solvates of its salts and N-oxides.

[0271] Preferably, the present invention also relates to a compound of formula (I), wherein

[0272] T is O or S,

[0273] n is 0 or 1,

[0274] m is 0 or 1,

[0275] A is N or CR 8 ,

[0276] wherein

[0277] R 8 is hydrogen or halogen,

[0278] R 1 is hydrogen, C1-C4-alkyl, -C(=O)R 10 , -C(=O)(OR 11 ) or -C(=O)N(R 13 )2,

[0279] wherein

[0280] R 10 , R 11 and R 12 are independently C1-C 64 -alkyl, C3-C6-cycloalkyl or C2-C4-alkenyl,

[0281] R 2 and R 3 are independently hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxycarbonyl or C3-C6-cycloalkyl,

[0282] or

[0283] R 2 and R 3 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0284] R 4 and R 5 are independently hydrogen, halogen, hydroxy, C1-C4-alkyl or C1-C4-haloalkyl,

[0285] or

[0286] R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0287] or

[0288] R 2 and R 4 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0289] and

[0290] R 3 and R 5 are independently hydrogen or halogen,

[0291] or

[0292] R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## ,

[0293] wherein

[0294] ** is the point of attachment to N(R 1 ),

[0295] ## is the point of attachment to R 6 ,

[0296] and

[0297] R 3 and R 5 are independently hydrogen or C1-C4-alkyl,

[0298] R 6 is a C7-C 12 -carbocyclic group, phenyl, naphthyl, 7- to 12-membered heterocyclic group, 5- to 12-membered heteroaryl group, C7-C 12 -carbocyclic group oxy, phenoxy, naphthoxy, 7- to 12-membered heteroaryloxy, 7- to 12-membered heterocyclic group oxy, C1-C3-alkoxy or C1-C3-haloalkoxy,

[0299] wherein the C1-C3-alkoxy and C1-C3-haloalkoxy are independently substituted by a substituent selected from the following: C7-C 12 -carbocyclic group, phenyl, naphthyl, 5- to 12-membered heterocyclic group and 5- to 12-membered heteroaryl group,

[0300] wherein the C7-C 12 -carbocyclic group, phenyl, naphthyl, 5- to 12-membered heterocyclic group and 5- to 12-membered heteroaryl group are each optionally substituted by 1 to 3 R 6S substituents, wherein the C7-C 12 -carbocyclic group, phenyl, naphthyl, 7- to 12-membered heterocyclic group, 5- to 12-membered heteroaryl group, C7-C 12 -carbocyclic group oxy, phenoxy, naphthoxy, 7- to 12-membered heteroaryloxy, 7- to 12-membered heterocyclic group oxy are optionally substituted by 1 to 3 R 6S substituents,

[0301] wherein

[0302] R 6S is halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, naphthyl, 5- or 6-membered heteroaryl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuryl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R 16 or -C(=O)(OR 17 ),

[0303] Among them, the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl are further optionally substituted by 1 or 2 substituents independently selected from the following: cyano, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, -O-Si(C1-C4-alkyl)3, –Si(C1-C4-alkyl)3, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and 3- to 7-membered heterocyclic group,

[0304] and

[0305] among them, the C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, naphthyl, 5- or 6-membered heteroaryl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl are further optionally substituted by 1 or 2 substituents independently selected from the following: halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxycarbonyl,

[0306] and, among them

[0307] R 16 and R 17 are independently C1-C4-alkyl,

[0308] Ring Y together with the pyridine ring or pyridazine ring forms a group of formula (II-a) to (II-v),

[0309]

[0310]

[0311] wherein

[0312] * is the point of connection to the group -O-Q,

[0313] # is the point of connection to -N(R 1 )

[0314] p is 0, 1, 2, 3 or 4,

[0315] x 1 is 1 or 2,

[0316] x 2 is 0, 1 or 2,

[0317] R 7A 、R 7B 、R 7C 、R 7D 、R 7E 、R7F and R 7G are independently hydrogen, hydroxy, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,

[0318] R 7H is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl,

[0319] R 7K is methylene, halomethylene, halogen, hydroxy, oxo, C1-C4-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl,

[0320] or

[0321] two substituents R 7K together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0322] Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxanyl, [1,3]dioxolo[4,5-b]pyridyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furanopyridyl, thienothiophenyl or thienothiazolyl,

[0323] wherein the phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxanyl, [1,3]dioxolo[4,5-b]pyridyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furanopyridyl, thienothiophenyl or thienothiazolyl are optionally substituted by 1 to 3 Qs independently selected from the following SSubstituted by substituents: halogen, cyano, nitro, hydroxy, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkyl, oxetanyl and -N(R 43 )2,

[0324] wherein

[0325] said C3-C6-cycloalkyl and oxetanyl are each optionally substituted by 1 or 2 substituents independently selected from the following: halogen, C1-C4-alkyl and C1-C4-haloalkyl,

[0326] R 43 is hydrogen and C1-C6-alkyl,

[0327] and its N-oxides, salts, solvates and solvates of its salts and N-oxides.

[0328] More preferably, the present invention also relates to a compound of formula (I), wherein

[0329] T is O or S,

[0330] n is 0 or 1,

[0331] m is 0 or 1,

[0332] A is N or CR 8 ,

[0333] wherein

[0334] R 8 is hydrogen or methyl,

[0335] R 1 is hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy or -C(=O)R 10 ,

[0336] wherein

[0337] R 10 is methyl or ethyl,

[0338] R 2 and R 3 are hydrogen,

[0339] R 4 and R 5 are independently hydrogen, fluorine, methyl or ethyl,

[0340] or

[0341] R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## ,

[0342] wherein

[0343] ** is the point of attachment to N(R 1 ),

[0344] ## is the point of attachment to R 6 ,

[0345] and

[0346] R 3 and R 5 are hydrogen,

[0347] R 6 is tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzothiazolyl, phenoxy or benzyloxy,

[0348] wherein tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzothiazolyl, phenoxy or benzyloxy is optionally substituted by 1 to 3 R 6S substituents,

[0349] wherein

[0350] R 6S is independently halogen, cyano, oxo, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C5-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl or -C(=O)R 16 ,

[0351] wherein

[0352] R 16 is a C1-C4-alkyl group,

[0353] Ring Y together with the pyridine ring or pyridazine ring forms a group of formula (II-a), (II-b), (II-g), (II-h), (II-i), (II-r), (II-s), (II-u) or (II-v),

[0354]

[0355]

[0356] wherein

[0357] * is the point of attachment to the group -O-Q,

[0358] # is the point of attachment to -N(R 1 ),

[0359] p is 0, 1 or 2,

[0360] x 1 is 1 or 2,

[0361] x 2 is 0, 1 or 2,

[0362] G is O or NR 7L ,

[0363] wherein

[0364] R 7L is hydrogen,

[0365] R 7A is hydrogen,

[0366] R 7B is hydrogen, fluorine, methyl or methoxy,

[0367] R 7C is hydrogen, fluorine, methyl or methoxy,

[0368] R 7D is hydrogen,

[0369] R 7E is hydrogen,

[0370] R 7F is hydrogen, and

[0371] R 7K is hydroxy or methyl,

[0372] Q is phenyl, pyridyl or pyrimidinyl,

[0373] wherein the phenyl, pyridyl and pyrimidinyl are optionally substituted by 1 or 2 substituents Q independently selected from the following S substituents: halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, cyclopropyl and cyclobutyl,

[0374] as well as their N-oxides, salts, solvates and solvates of their salts and N-oxides.

[0375] Equally more preferably, the present invention relates to a compound of formula (I), wherein

[0376] T is O or S,

[0377] n is 0 or 1,

[0378] m is 0 or 1,

[0379] A is N or CR 8 ,

[0380] wherein

[0381] R 8 is hydrogen,

[0382] R 1 is hydrogen or -C(=O)R 10 ,

[0383] wherein

[0384] R 10 is C1-C4-alkyl,

[0385] R 2 and R 3 are independently hydrogen, fluorine, methyl or ethyl,

[0386] R 4 and R 5 are independently hydrogen, fluorine, methyl or ethyl,

[0387] or

[0388] R 4 and R 5 together with the carbon atom to which they are attached form a cyclopropyl ring,

[0389] or

[0390] R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## group,

[0391] wherein

[0392] **is the point connected to N(R 1 ),

[0393] ## is the point connected to R 6 ),

[0394] and

[0395] R 3 and R 5 are independently hydrogen,

[0396] R 6 is tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, benzothiazolyl, phenyloxy or benzyloxy,

[0397] wherein tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, benzothiazolyl, phenyloxy and benzyloxy are optionally substituted by 1 to 3 R 6S substituents,

[0398] wherein

[0399] R 6S is independently halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl or -C(=O)R 16 ,

[0400] wherein

[0401] R 16 is C1-C4-alkyl,

[0402] Ring Y together with the pyridine ring or the pyridazine ring forms a group of formula (II-a), (II-b), (II-g), (II-h), (II-r), (II-s), (II-u) or (II-v),

[0403]

[0404]

[0405] wherein

[0406] * is the point of attachment to the group -O-Q,

[0407] # is the point of attachment to -N(R 1 ),

[0408] p is 0, 1 or 2,

[0409] x 1 is 1 or 2,

[0410] x 2 is 0, 1 or 2,

[0411] R 7A is hydrogen or C1-C4-alkyl,

[0412] R 7B is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy,

[0413] R 7C is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy,

[0414] R 7D is hydrogen,

[0415] R 7E is hydrogen,

[0416] R 7F is hydrogen,

[0417] R 7K is hydroxy, C1-C4-alkyl or C1-C4-alkoxy,

[0418] Q is phenyl or pyridyl,

[0419] wherein the phenyl and pyridyl are optionally substituted by 1 or 2 substituents independently selected from the following S substituents: halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, cyclopropyl and cyclobutyl, and their N-oxides, salts, solvates and solvates of their salts and N-oxides.

[0420] Even more preferably, T is O.

[0421] Even more preferably, n is 1 and m is 1.

[0422] Preferably, R 1is hydrogen, hydroxy, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, -C(=O)R 10 or -C(=O)(OR 11 ), where R 10 and R 11 are independently C1-C6-alkyl or C2-C6-alkenyl.

[0423] More preferably, R 1 is hydrogen or -C(=O)R 10 , where R 10 is C1-C6-alkyl.

[0424] Even more preferably, R 1 is hydrogen.

[0425] Non-limiting examples of suitable R 1 include any R 1 group disclosed in the "R 1 " column of Table 1.

[0426] Preferably, R 2 and R 3 are independently hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxycarbonyl or C3-C6-cycloalkyl, or, R 2 and R 3 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl-ring.

[0427] More preferably, R 2 and R 3 are independently hydrogen or C1-C4-alkyl, or, R 2 and R 3 together with the carbon atom to which they are attached form a cyclopropyl-ring.

[0428] Preferably, R 4 and R 5 are independently hydrogen, halogen, hydroxy, C1-C4-alkyl or C1-C4-haloalkyl, or, R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl-ring.

[0429] More preferably, R 4 and R 5 are independently hydrogen or fluorine, or, R 4 and R 5 together with the carbon atom to which they are attached form a cyclopropyl-ring.

[0430] Preferably, R 2 and R4 A cyclopropyl-ring is formed, and R 3 and R 5 are independently hydrogen or halogen.

[0431] More preferably, R 1 is hydrogen, R 2 and R 3 are independently hydrogen or C1-C4-alkyl, R 4 and R 5 are independently hydrogen or fluorine, or, R 4 and R 5 together with the carbon atom to which they are attached form a cyclopropyl-ring.

[0432] Even more preferably, n is 0 or 1, m is 0 or 1, R 2 and R 3 are hydrogen, R 4 and R 5 are independently hydrogen, fluorine, methyl or ethyl,

[0433] or

[0434] R 4 and R 5 together with the carbon atom to which they are attached form a cyclopropyl-ring.

[0435] or

[0436] R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## wherein ** is the point of attachment to N(R 1 ) and ## is the point of attachment to R 6 .

[0437] Preferably, R 6 is a C7-C 14 -carbocyclic group, a C6-C 12 -aryl, a 5- to 12-membered heterocyclic group, a 5- to 12-membered heteroaryl, a C6-C 14 -aryloxy and a C1-C3-alkoxy, each substituted by a C6-C 14 -aryl,

[0438] wherein the C6-C 14 -aryl is optionally substituted by 1 to 3 substituents R 6S ,

[0439] wherein the C7-C 12 -carbocyclic group, the C6-C 14-aryl, 5- to 12-membered heterocyclic group, 5- to 12-membered heteroaryl, C6-C 14 -aryloxy is optionally substituted with 1 to 3 substituents R 6S substituted,

[0440] wherein

[0441] R 6S is independently selected from halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R 16 and -C(=O)(OR 17 ),

[0442] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are further optionally substituted with 1 or 2 substituents independently selected from: cyano, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and 3- to 7-membered heterocyclic group, and wherein the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl and tetrahydropyranyl are further optionally substituted with 1 or 2 substituents independently selected from: halogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxycarbonyl, and wherein R 16 is C1-C6-alkyl, R 17 is hydrogen or C1-C6-alkyl.

[0443] More preferably, R 6is phenyl, naphthyl, indanyl, tetrahydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-1,2'-indane]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzothienyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothienyl, dihydro-4H-cyclopenta[b]thienyl, dihydro-4H-cyclopenta[d]thiazolyl, tetrahydropyrazolo[1,5-a]pyridinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thienyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl or thieno[2,3-d]isothiazolyl,

[0444] wherein phenyl, naphthyl, indanyl, tetrahydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-1,2'-indan]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzothienyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothienyl, dihydro-4H-cyclopenta[b]thiophenyl, dihydro-4H-cyclopenta[d]thiazolyl, tetrahydropyrazolo[1,5-a]pyridinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl or thieno[2,3-d]isothiazolyl is optionally substituted by 1 or 2 substituents R independently selected from the following 6S Substituted with: halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, -C(=O)R 16 and -C(=O)(OR 17 ), wherein the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl and pyridyl are further optionally substituted by 1 or 2 substituents independently selected from: fluorine, chlorine, C1-C4-alkyl and C1-C4-haloalkyl, and wherein, R 16 is C1-C4-alkyl and R 17 is hydrogen or C1-C4-alkyl.

[0445] Even more preferably, R 6 is tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, benzothiazolyl, phenyloxy or benzyloxy,

[0446] wherein the tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, benzothiazolyl, phenyloxy or benzyloxy is optionally substituted by 1 or 2 substituents R 6S wherein R 6S is independently halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl or -C(=O)R 16 and wherein R 16 is C1-C4-alkyl.

[0447] In an even more preferred embodiment, R 6 is

[0448]

[0449] wherein

[0450] § 1 is the point connected to C(R 4 R 5 ) m and

[0451] R 6S1 and R 6S2 are independently hydrogen or R 6S ,

[0452] wherein

[0453] R 6Sis halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl or pyrazolyl,

[0454] wherein the C3-C6-cycloalkyl and pyrazolyl are optionally substituted by 1 or 2 substituents independently selected from halogen and C1-C4-alkyl,

[0455] with the proviso that R 6s1 and R 6s2 are at least one different from hydrogen.

[0456] Preferably, n is 0, m is 0, and

[0457] R 6 is naphthyl, indanyl, tetrahydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-1,2'-dihydroindene]-1-yl, spiro[cyclopropane-1,2'-tetrahydronaphthalene]-1-yl, dihydrobenzofuranyl, dihydrobenzothienyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothienyl, dihydro-4H-cyclopenta[b]thienyl, dihydro-4H-cyclopenta[d]thiazolyl, tetrahydropyrazolo[1,5-a]pyridinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thienyl, imidazo[2,1-b]oxazolyl, furano[2,3-d]isoxazolyl or thieno[2,3-d]isothiazolyl,

[0458] Among them, naphthyl, indanyl, tetrahydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-1,2'-indane]-1-yl, spiro[cyclopropane-1,2'-tetrahydronaphthalene]-1-yl, dihydrobenzofuranyl, dihydrobenzothienyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, dihydro-5H-cyclopenta[b]pyridyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothienyl, dihydro-4H-cyclopenta[b]thienyl, dihydro-4H-cyclopenta[d]thiazolyl, tetrahydropyrazolo[1,5-a]pyridyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridyl, tetrahydroimidazo[1,2-a]pyridyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridyl, imidazo[1,2-a]pyridyl, [1,2,4]triazolo[4,3-a]pyridyl, imidazo[1,2-a]pyridyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, furano[2,3-d]isoxazolyl and thieno[2,3-d]isothiazolyl are optionally substituted by 1 or 2 substituents R 6S substituted,

[0459] wherein

[0460] R 6S is independently selected from halogen, cyano, oxo, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, -C(=O)R 16 and -C(=O)(OR 17 ),

[0461] wherein, the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl and pyridyl are further optionally substituted by 1 or 2 substituents independently selected from the following: fluorine, chlorine, C1-C4-alkyl and C1-C4-haloalkyl,

[0462] and, wherein

[0463] R 16 is a C1-C4-alkyl group,

[0464] R 17 is hydrogen or a C1-C4-alkyl group.

[0465] More preferably, n is 0, m is 0, and

[0466] R 6 is tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, indolyl or benzothiazolyl,

[0467] wherein the tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, indolyl and benzothiazolyl are optionally substituted with 1 to 3 R 6S substituents,

[0468] wherein

[0469] R 6S is halogen, cyano, oxo, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C5-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl or -C(=O)R 16 ,

[0470] R 16 is a C1-C4-alkyl group.

[0471] Preferably, n is 0 or 1, m is 1, and

[0472] R 6 is phenyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, phenyloxy or benzyloxy,

[0473] wherein the phenyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, phenyloxy or benzyloxy are optionally substituted with 1 or 2 substituents R 6S substituted,

[0474] wherein

[0475] R 6SIndependently being halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl or -C(=O)R 16 ,

[0476] wherein

[0477] R 16 is C1-C4-alkyl.

[0478] More preferably, n is 0 or 1, m is 1, and

[0479] R 6 is phenyl,

[0480] wherein the phenyl is optionally substituted by 1 or 2 substituents R 6S substituted,

[0481] wherein

[0482] R 6S is independently halogen, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl.

[0483] Suitable non-limiting examples of the chain include any chain disclosed in the columns of Table 1.

[0484] Preferably, p is 0, 1, 2 or 3. More preferably, p is 0, 1 or 2.

[0485] Preferably, x 1 is 1 or 2 and x 2 is 0, 1 or 2. More preferably, x 1 is 1 or 2 and x 2 is 0, 1 or 2.

[0486] Preferably, R 7A , R 7B , R 7C , R 7D , R 7E , R 7F and R 7G are independently hydrogen, hydroxy, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy, R 7His hydrogen, C1-C4-alkyl or C1-C4-haloalkyl, and R 7K is halogen, hydroxy, oxo, C1-C4-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl.

[0487] More preferably, R 7A is hydrogen or C1-C4-alkyl, R 7B is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy, R 7C is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy, R 7D is hydrogen, R 7E is hydrogen, R 7F is hydrogen, and R 7K is hydroxy, C1-C4-alkyl or C1-C4-cycloalkyl.

[0488] Preferably, ring Y together with the pyridine ring or pyridazine ring forms a bicyclic heterocyclic group or bicyclic heteroaryl group respectively, wherein the bicyclic heterocyclic group or bicyclic heteroaryl group contains 3 to 6 double bonds and 1 to 4 heteroatoms or a group selected from N, O, S, SO and SO2.

[0489] More preferably, ring Y together with the pyridine ring or pyridazine ring forms furano[3,2-b]pyridine, furano[3,2-c]pyridazine, thieno[2,3-b]pyridine, thieno[2,3-c]pyridazine, thieno[3,2-b]pyridine, thieno[3,2-c]pyridazine, thiazolo[5,4-b]pyridine, thiazolo[5,4-c]pyridazine, oxazolo[5,4-b]pyridine, oxazolo[5,4-c]pyridazine, oxazolo[4,5-b]pyridine, oxazolo[4,5-c]pyridazine, thiazolo[4,5-b]pyridine, thiazolo[4,5-c]pyridazine, 1H-imidazo[4,5-b]pyridine, 5H-imidazo[4,5-c]pyridazine, 3H-imidazo[4,5-b]pyridine, 7H-imidazo[4,5-c]pyridazine, 1,5-naphthyridine, pyrido[3,2-c]pyridazine, quinoline, cinnoline, pyrido[3,2-d]pyrimidine, pyrimido[5,4-c]pyridazine, pyrido[3,4-c]pyridazine, pyrido[2,3-b]pyrazine, tetrahydroquinoline, tetrahydrocinnoline, dihydro-5H-cyclopenta[c]pyridazine, dihydro-5H-cyclopenta[c]pyridine, 2,3-dihydro-[1,4]dioxino[2,3-b]pyridine, 6,7-dihydro-[1,4]dioxino[2,3-b]pyridazine, 7,8-dihydro-5H-pyrano[4,3-c]pyridazine, 5,6,7,8-tetrahydropyrido[3,2-c]pyridazine, 5,6,8,9-tetrahydrooxazolo[4,5-c]pyridazine or 7,8-dihydro-6H-[1,4]dioxazolo[2,3-c]pyridazine.

[0490] Even more preferably, ring Y together with the pyridine ring or the pyridazine ring forms a group of formula (II-a), (II-b), (II-g), (II-h), (II-r), (II-s), (II-u) or (II-v) respectively

[0491]

[0492] wherein

[0493] * is the point of attachment to the group -O-Q,

[0494] # is the point of attachment to -N(R 1 ),

[0495] p is 0, 1 or 2,

[0496] x 1 is 1 or 2,

[0497] x 2 is 0, 1 or 2,

[0498] R 7A is hydrogen or C1-C4-alkyl,

[0499] R 7B is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy,

[0500] R 7C is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy,

[0501] R 7D is hydrogen,

[0502] R 7E is hydrogen,

[0503] R 7F is hydrogen,

[0504] R 7K is hydroxy, C1-C4-alkyl or C1-C4-alkoxy.

[0505] Equally more preferably, ring Y together with the pyridine ring or the pyridazine ring forms a group of formula (II-a), (II-b), (II-g), (II-h), (II-r), (II-s), (II-u) or (II-v) respectively. Ring Y together with the pyridine ring or the pyridazine ring forms a group of formula (II-a), (II-b), (II-g), (II-h), (II-i), (II-r), (II-s), (II-u) or (II-v) respectively,

[0506]

[0507] wherein

[0508] * is the point connected to the group - O - Q,

[0509] # is the point connected to - N(R 1 ),

[0510] p is 0, 1 or 2,

[0511] x 1 is 1 or 2,

[0512] x 2 is 0, 1 or 2,

[0513] G is O or NR 7L ,

[0514] wherein

[0515] R 7L is hydrogen,

[0516] R 7A is hydrogen,

[0517] R 7B is hydrogen, fluorine, methyl or methoxy,

[0518] R 7C is hydrogen, fluorine, methyl or methoxy,

[0519] R 7D is hydrogen,

[0520] R 7E is hydrogen,

[0521] R 7F is hydrogen,

[0522] and

[0523] R 7K is hydroxyl or methyl.

[0524] Preferably, Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxanyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thiophenyl or thieno[2,3-d]thiazolyl, wherein phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxanyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thiophenyl or thieno[2,3-d]thiazolyl is optionally substituted with 1 to 4 substituents Q S substituted, wherein

[0525] Q S is independently halogen, cyano, nitro, hydroxy, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkyl, oxetanyl or -N(R 43 )2, wherein the C3-C6-cycloalkyl and oxetanyl are each optionally substituted with 1 or 2 substituents independently selected from the following: halogen, C1-C4-alkyl and C1-C4-haloalkyl, and wherein R 43is hydrogen or a C1-C6-alkyl group.

[0526] More preferably, Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridyl, thienyl or indolyl, wherein phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridyl, thienyl and indolyl are optionally substituted with 1 to 3 substituents Q S wherein

[0527] Q S is independently halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkynyl or C3-C6-cycloalkyl, wherein the C3-C6-cycloalkyl and oxetanyl are each optionally substituted with 1 or 2 substituents independently selected from fluorine or methyl.

[0528] Even more preferably, Q is phenyl or pyridyl, wherein phenyl or pyridyl is optionally substituted with 1 or 2 substituents Q independently selected from the following S substituents: halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, cyclopropyl or cyclobutyl.

[0529] Even more preferably, Q is

[0530]

[0531] wherein

[0532] §2 is the point of attachment to the oxygen atom,

[0533] Q S1 is hydrogen or fluorine,

[0534] Q S2 is hydrogen, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl or cyclobutyl,

[0535] provided that at least one of Q S1 and Q S2 is different from hydrogen.

[0536] Non-limiting examples of suitable Q include any Q group listed in the "Q" column of Table 1.

[0537] m, n, p, R specifically defined above 1 、R 2 、R 3 、R4 , R 5 , R 6 , R 7 , R 8 , A, T, Y, and Q (broad definitions as well as preferred, more preferred, and even more preferred definitions) can be combined in different ways. Thus, combinations of these definitions provide subsets of compounds according to the invention, such as the compounds disclosed below.

[0538] The invention also relates to compounds of any formula (I) disclosed in Table 1.

[0539] Compounds obtained by combinations that are contrary to the laws of nature and that a person skilled in the art would thus exclude based on his / her expertise are not covered herein. For example, ring structures having three or more adjacent oxygen atoms are excluded.

[0540] The compounds of formula (I) can suitably be in their free form, salt form, N-oxide form, or solvate form (e.g., hydrate).

[0541] Depending on the nature of the substituents, the compounds of formula (I) can exist in different stereoisomeric forms. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers, or geometric isomers. Thus, the invention encompasses pure stereoisomers and any mixtures of these isomers. When a compound can exist in more than two tautomeric forms in equilibrium, the compound mentioned by means of one tautomeric description should be considered to include all tautomeric forms.

[0542] Depending on the number of double bonds in the compound, any compound of the invention can also exist in one or more geometric isomeric forms. Depending on the nature of the substituents on the double bond or the ring, the geometric isomers can exist in the cis (=Z-) or trans (=E-) form. Thus, the invention also relates to all geometric isomers and all possible mixtures in all ratios.

[0543] Depending on the nature of the substituents, the compounds of formula (I) can exist in the form of their free compounds and / or salts (such as agrochemically active salts).

[0544] Agrochemically active salts include acid addition salts of inorganic and organic acids and salts of conventional bases. Examples of inorganic acids are hydrohalic acids (such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid), sulfuric acid, phosphoric acid and nitric acid, and acid salts (such as sodium bisulfate and potassium bisulfate). Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids (such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid), as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono-unsaturated or di-unsaturated fatty acids having 6 to 20 carbon atoms, alkyl sulfuric acid monoesters, alkyl sulfonic acids (sulfonic acids having straight-chain or branched-chain alkyl groups with 1 to 20 carbon atoms), aryl sulfonic acids or aryl disulfonic acids (aromatic groups such as phenyl and naphthyl with one or two sulfonic acid groups), alkyl phosphonic acids (phosphonic acids having straight-chain or branched-chain alkyl groups with 1 to 20 carbon atoms), aryl phosphonic acids or aryl diphosphonic acids (aromatic groups such as phenyl and naphthyl with one or two phosphonic acid groups), where the alkyl and aryl groups may carry other substituents, such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

[0545] A solvate of a compound or a salt thereof according to the invention is a stoichiometric composition of the compound with a solvent.

[0546] The compounds of the invention can exist in a variety of crystalline and / or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates and hydrates.

[0547] The compounds of formula (I) can be used as fungicides (for controlling phytopathogenic fungi), in particular in a method for controlling phytopathogenic fungi, which method comprises the step of applying one or more compounds of formula (I) to a plant.

[0548] Processes for preparing compounds of formula (I) and intermediates

[0549] The present invention relates to methods for preparing the compounds of formula (I) and their intermediates. Unless otherwise specified, the groups A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , T, Y, n, m, p and Q have the meanings given above for the compounds of formula (I). These definitions apply not only to the final products of formula (I) but also to all intermediates.

[0550] The compounds of formula (I-a)-(I-b) are various subsets of formula (I). The compounds of formula (I-a-1)-(I-a-3) are various subsets of formula (I-a). Unless otherwise specified, all substituents of formula (I-a)-(I-b) and (I-a-1)-(I-a-3) are as defined above for formula (I).

[0551] The compounds of general formula (I) can be prepared by various routes similar to known methods (see the examples and references herein). Non-limiting examples of suitable methods are described herein.

[0552] The compounds of formula (I) can be obtained directly by implementing method A, B or C, or can be obtained by transforming or derivatizing another compound of formula (I) prepared according to the methods described herein. For example, a compound of formula (I) can be transformed into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) with other substituents.

[0553] The methods described herein can be appropriately carried out using one or more organic solvents that are generally inert to the reactions under consideration. Suitable inert organic solvents can be selected from the following: aliphatic, cycloaliphatic or aromatic hydrocarbons (such as petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, light petroleum, benzene, toluene, xylene or decalin), halogenated aliphatic, cycloaliphatic or aromatic hydrocarbons (such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane), ethers (such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole), ketones (such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone), esters (such as methyl acetate, ethyl acetate or butyl acetate), alcohols (such as methanol, ethanol, propanol, isopropanol, butanol, tert-butanol), nitriles (such as acetonitrile, propionitrile, n-butyl nitrile or isobutyl nitrile or benzonitrile), amides (such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide), sulfoxides (such as dimethyl sulfoxide) or sulfones (such as sulfolane), ureas (such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone) or any mixture thereof.

[0554] Some of the methods described herein may require or optionally use one or more inorganic or organic bases commonly used in the reaction. Examples of suitable inorganic and organic bases include, but are not limited to, alkaline earth metal or alkali metal carbonates (such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate), alkali metal hydrides (such as sodium hydride), alkaline earth metal or alkali metal hydroxides (such as sodium hydroxide, calcium hydroxide, potassium hydroxide or other ammonium hydroxide derivatives), fluorides of alkaline earth metal, alkali metal or ammonium (such as potassium fluoride, cesium fluoride or tetrabutylammonium fluoride), alkali metal or alkaline earth metal acetates (such as sodium acetate, lithium acetate, potassium acetate or calcium acetate), alkali metal alkoxides (such as potassium tert-butoxide, sodium tert-butoxide), alkali metal phosphates (such as tripotassium phosphate), tertiary amines (such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dicyclohexylmethylamine, N,N-diisopropylethylamine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN), diazabicycloundecene (DBU), quinuclidine, 3-acetoxyquinuclidine, guanidine or aromatic bases (such as pyridine, methylpyridine, dimethylpyridine or trimethylpyridine).

[0555] Some of the methods described herein may optionally be carried out in the presence of a transition metal catalyst (such as a metal (such as copper or palladium) salt or complex), and if appropriate, in the presence of a ligand.

[0556] Suitable copper salts or complexes and their hydrates include, but are not limited to, copper metal, cuprous iodide (I), cuprous chloride (I), cuprous bromide (I), copper(II) chloride, copper(II) bromide, copper(II) oxide, copper(I) oxide, copper(II) acetate, cuprous acetate (I), cuprous thiophene-2-carboxylate (I), cuprous cyanide (I), copper(II) sulfate, bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II), copper(II) trifluoromethanesulfonate, copper(I) tetra(acetonitrile)hexafluorophosphate, copper(I) tetra(acetonitrile)tetrafluoroborate.

[0557] By adding a copper salt and a ligand or a salt thereto separately to the reaction, a suitable copper complex can also be formed in situ in the reaction mixture, and the ligand or the salt is, for example, ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, rac-trans-1,2-diaminocyclohexane, rac-trans-N,N'-dimethylcyclohexane-1,2-diamine, 1,1'-binaphthyl-2,2'-diamine, N,N,N',N'-tetramethylethylenediamine, proline, N,N-dimethylglycine, quinolin-8-ol, pyridine, 2-aminopyridine, 4-(dimethylamino)pyridine, 2,2'-bipyridyl, 2,6-bis(2-pyridyl)pyridine, 2-pyridinecarboxylic acid, 2-(dimethylaminomethyl)-3-hydroxypyridine, 1,10-phenanthroline, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-dimethyl-1,10-phenanthroline, 4,7-dimethoxy-1,10-phenanthroline, N,N'-bis[(E)-pyridin-2-ylmethylene]cyclohexane-1,2-diamine, N-[(E)-phenylmethylene], N-[(E)-phenylmethylene]-cyclohexylamine, 1,1,1-tris(hydroxymethyl)ethane, ethylene glycol, 2,2,6,6-tetramethylheptane-3,5-dione, 2-(2,2-dimethylpropanoyl)cyclohexanone, acetylacetone, dibenzoylmethane, 2-(2-methylpropanoyl)cyclohexanone, biphenyl-2-yl(di-tert-butyl)phosphane, vinylbis(diphenylphosphine), N,N-diethylsalicylamide, 2-hydroxybenzaldoxime, oxo[(2,4,6-trimethylphenyl)amino]acetic acid or 1H-pyrrole-2-carboxylic acid.

[0558] Suitable palladium salts or complexes include, but are not limited to, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium(0), bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), bis(triphenylphosphine)palladium(II) dichloride, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride, bis(cinnamyl)dichlorodipalladium(II), bis(allyl)-dichlorodipalladium(II) or [1,1'-bis(di-tert-butylphosphino)ferrocene]palladium(II) dichloride.

[0559] The palladium complex can also be generated in the reaction mixture by adding the palladium salt and the ligand or salt separately to the reaction, wherein the ligand or salt is, for example, triethylphosphine, tri-tert-butylphosphine, tri-tert-butylphosphine tetrafluoroborate, tricyclohexylphosphine, 2-(dicyclohexylphosphine)biphenyl, 2-(di-tert-butylphosphine)biphenyl, 2-(dicyclohexylphosphine)-2'-(N,N-dimethylamino)biphenyl, 2-(tert-butylphosphine)-2'-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphine-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphine-2,6'-dimethoxybiphenyl, 2-dicyclohexylphosphine-2',6'-diisopropylbiphenyl, triphenylphosphine, tri-(o-methyl)-biphenyl, phenyl)phosphine, sodium 3-(diphenylphosphino)benzenesulfonate, tri-(2-methoxy-phenyl)phosphine, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)ethane, 1,4-bis(dicyclohexylphosphino)butane, 1,2-bis(dicyclohexylphosphino)ethane, 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)-biphenyl, 1,1'-bis(diphenylphosphino)-ferrocene, (R)-(-)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, tri-(2,4-tert-butyl-phenyl)phosphite, di(1-adamantyl)-2-morpholinophenylphosphine or 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride.

[0560] Suitable catalysts and / or ligands can be selected from commercial catalogues, such as "Metal Catalysts for Organic Synthesis" by Strem Chemicals, or from reviews (Chemical Society Reviews (2014), 43, 3525, Coordination Chemistry Reviews (2004), 248, 2337 and references therein).

[0561] Some of the methods described herein can be carried out by metal photoredox catalysis according to methods documented in the literature (Nature chemistry review, (2017) 0052 and references therein; Science (2016) 352, 6291, 1304; Org. Lett. 2016, 18, 4012, J. Org. Chem 2016, 81, 6898; J. Am. Chem. Soc. 2016, 138, 12715, J. Am. Chem. Soc. 2016, 138, 13862; J. Am. Chem. Soc. 2016, 138, 8034; J. Org. Chem. 2016, 81, 12525, J. Org. Chem. 2015, 80, 7642). Then the method H is carried out in the presence of a photosensitizer (such as Ir and Ru complexes or organic dyes) and a metal catalyst (such as Ni complexes). The reaction can be carried out in the presence of a ligand and, if appropriate, in the presence of a base under blue or white light irradiation.

[0562] Suitable photosensitizers include but are not limited to Ir(III) photocatalysts such as [Ir(dFCF3ppy)2(bpy)]PF6 (dFCF3ppy = 2-(2,4-difluorophenyl)-5-trifluoromethylpyridine, bpy = 2,2'-bipyridine), [Ir(dFCF3ppy)2(dtbbpy)]PF6 (dtbbpy = 4,4'-di-tert-butyl-2,2'-bipyridine), Ir(ppy)2(dtbbpy)PF6 (ppy = 2-phenylpyridine), Ir(ppy)2(bpy)PF6, Ir(dFppy)3PF6 (dFCF3ppy = 2-(2,4-difluorophenyl)pyridine), fac-Ir(ppy)3, (Ir[diF(5-Me)ppy]2(tetraMePhen)PF6 (diF(5-Me)ppy = 2-(2,4-difluorophenyl)-5-methylpyridine, tetraMePhen = 3,4,7,8-tetramethyl-1,10-phenanthroline); Ru(II) photocatalysts such as Ru(bpy)3Cl2 or Ru(bpy)3(PF6)2; or organic dyes such as 9-isopropylidene-10-acridone, salts such as perchlorate or tetrafluoroborate, or 2,4,5,6-tetra-9H-carbazol-9-yl-1,3-benzenedicarbonitrile, 9-fluorenone and 9,10-phenanthrenequinone.

[0563] Suitable nickel catalysts include, but are not limited to, bis(1,5-cyclooctadiene)nickel(0) in anhydrous or hydrated form or as a dimethoxyethane complex, nickel(II) chloride, nickel(II) bromide, nickel(II) iodide; nickel(II) acetylacetonate, nickel(II) nitrate hexahydrate. These nickel catalysts can be used in combination with bipyridine ligands (such as 2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridine), or phenanthroline (such as 1,10-phenanthroline, 4,7-dimethyl-1,10-phenanthroline, 4,7-dimethoxy-1,10-phenanthroline) or diamines (such as N,N,N',N'-tetramethylethylenediamine) or diketones (such as tetramethylheptanedione).

[0564] The methods described herein can be carried out at temperatures from -105 °C to 250 °C, preferably from -78 °C to 185 °C.

[0565] The reaction time varies depending on the reaction scale and reaction temperature, but is generally between a few minutes and 48 hours.

[0566] The methods described herein are generally carried out at standard pressure. However, they can also be carried out at elevated or reduced pressure.

[0567] In the methods described herein, the starting materials are generally used in approximately equimolar amounts. However, a relatively large excess of one starting material can also be used.

[0568] Process for preparing a compound of formula (I)

[0569] Method A

[0570] The compound of formula (I-a) can be prepared by the method shown in Scheme 1, which comprises the step of reacting a compound of formula (1) with an amine of formula (2) or a salt thereof, wherein m, n, p, A, Q, Y, R in formula (I-a) 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined above, and

[0571] T is O,

[0572] R 1 is hydrogen, hydroxy, cyano or C1-C6-alkyl,

[0573] wherein m, A, Q, Y and R in formula (1) 7 are as defined above, and

[0574] U1 is hydroxy, halogen or C1-C6-alkoxy,

[0575] wherein m, n, R in formula (2) 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined above.

[0576]

[0577]

[0578] where U 1 is hydroxy can react with the amine of formula (2) in the presence of a condensing agent by a method described in the literature (e.g., Tetrahedron 2005, 61, 10827-10852). Examples of suitable condensing agents include, but are not limited to, halogenating reagents (e.g., phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride or thionyl chloride), dehydrating agents (e.g., ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride), carbodiimides (e.g., N,N'-dicyclohexylcarbodiimide (DCC)) or other conventional condensation (or peptide coupling) reagents (e.g., phosphorus pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), N,N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholine hydrochloride hydrate, tripyrrolidinophosphonium bromide hexafluorophosphate or propylphosphonic anhydride (T3P).

[0579] where U 1 is halogen can react with the amine of formula (2) in the presence of an acid-binding agent by a well-known method. Suitable acid-binding agents include any inorganic and organic bases commonly used in such reactions as described herein. Preferred are alkali metal carbonates, alkaline earth metal acetates, tertiary amines or aromatic bases.

[0580] where U 1 is C1-C6-alkoxy can react with an excess of the amine of formula (2), optionally in the presence of a Lewis acid (such as trimethylaluminum).

[0581] The compounds of formula (1) can be prepared by one or more of the methods described herein (see Methods E to L).

[0582] The amine of formula (2) is commercially available or can be prepared according to the methods described in the literature (such as WO2007 / 141009, WO2013 / 064460, WO2015 / 078800, WO2016 / 066574, US2006 / 0116370, WO2007 / 134799, WO2014 / 177487, WO2011 / 144338, EP0807629).

[0583] Method B

[0584] The compound of formula (I-a-1) can be prepared by reacting a compound of formula (3) with a compound of formula (4) in the presence of a base (such as an organic or inorganic base) (as shown in Scheme 2), where m, n, p, A, Q, Y, R in formula (I-a-1) 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined above, and

[0585] T is O,

[0586] R 1 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy,

[0587] wherein m, n, p, A, Y, R in formula (3) 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined above, and

[0588] X 1 is halogen,

[0589] wherein Q in formula (4) is as defined above.

[0590]

[0591] Method B can be carried out in the presence of a transition metal catalyst (such as a copper salt or complex), and if appropriate, in the presence of a ligand described herein.

[0592] The compound of formula (3) can be prepared by Method N.

[0593] The compound of formula (4) is commercially available or can be obtained by converting or derivatizing another compound of formula (4) according to well-known methods.

[0594] Method C

[0595] The compound of formula (I-a-2) can be prepared by a method comprising the step of reacting a compound of formula (5) with a reagent of formula (6) in the presence of a metal photoredox catalyst and a base (such as an organic or inorganic base) as described herein (as shown in Scheme 3), wherein m, n, p, A, Q, R in formula (I-a-2) 2 , R 3 , R 4 , R 5 , R 6 and R 7K are as defined above, and

[0596] T is O,

[0597] R 1 is hydrogen or C1-C6-alkyl,

[0598] wherein m, n, A, Q, R in formula (5) 2 , R 3 , R 4 , R 5 and R 6 are as defined above,

[0599] and

[0600] X 2 is halogen,

[0601] wherein p and R in formula (6) 7K are as defined above, and

[0602] Y 1 is CH, C-R 7K , O, S or S(=O)2,

[0603] x 1 is 1 or 2,

[0604] x 2 is 0, 1 or 2.

[0605]

[0606] The compound of formula (5) can be prepared by method M as described herein.

[0607] Method D

[0608] The compound of formula (I-b) can be prepared by a method as shown in Scheme 4, the method comprising the step of reacting a compound of formula (I-a-2) with a sulfurizing reagent, wherein m, n, p, A, Q, Y, R in formula (I-b) 2 , R 3 , R 4 , R5 , R 6 and R 7 as defined above, and

[0609] T is S,

[0610] R 1 is hydrogen,

[0611] wherein m, n, p, A, Q, Y, R in formula (I-a-2) 2 , R 3 , R 4 , R 5 , R 6 and R 7 as defined above, and

[0612] T is O,

[0613] R 1 is hydrogen.

[0614]

[0615] Suitable sulfurizing reagents for carrying out method D include, but are not limited to, sulfur (S), hydrogen sulfide (H2S), sodium sulfide (Na2S), sodium hydrosulfide (NaHS), boron trisulfide (B2S3), bis(diethylaluminum) sulfide ((AlEt2)2S), ammonium sulfide ((NH4)2S), phosphorus pentasulfide (P2S5), Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane-2,4-disulfide) or a polymer-supported sulfurizing reagent such as described in Journal of the Chemical Society, Perkin 1 (2001), 358.

[0616] Method H is optionally carried out in the presence of a catalytic amount of or a stoichiometric amount of or an excess of a base (inorganic and organic bases). Preferred are alkali metal carbonates (such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate), heterocyclic aromatic bases (such as pyridine, methylpyridine, dimethylpyridine, trimethylpyridine) and tertiary amines (such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylpyridin-4-amine or N-methyl-piperidine).

[0617] The compounds of formula (I-a-2) are a subset of the compounds of formula (I-a-1) and can be prepared by one or more of the methods described herein.

[0618] Process for preparing a compound of formula (1)

[0619] The compounds of formula (1) can be obtained directly by carrying out the methods described below, or can be obtained by transforming or derivatizing another compound of formula (1) prepared according to the methods described herein. The compounds of formula (1-a)-(1-f) are various subsets of formula (1). The compounds of formula (1-a1) and (1-a2) are various subsets of formula (1-a), and the compounds of formula (1-b1) and (1-b2) are various subsets of formula (1-b).

[0620] Method E

[0621] The compounds of formula (1-a1) can be prepared by the method shown in Scheme 5, which comprises the step of reacting a compound of formula (10) with carbon monoxide, carbon dioxide or a reagent of formula (11), wherein p, A and Q in formula (1-a1) are as defined above, and

[0622] U 1 is hydroxy or C1-C6-alkoxy,

[0623] Y 1 、Y 2 、Y 3 and Y 4 are independently C-H, C-R 7 or N,

[0624] wherein

[0625] R 7 is as defined above,

[0626] wherein A, Q, Y 1 、Y 2 、Y 3 and Y 4 in formula (10) are as defined above, and

[0627] X 3 is halogen,

[0628] wherein

[0629] E 1 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy,

[0630] U 2 is C1-C6-alkoxy.

[0631]

[0632] The compounds of formula (8) (wherein A, Y 1 、Y 2 、Y 3 and Y 4As defined above, and X 3 (wherein X is halogen) is commercially available or can be prepared according to the methods described in the literature (WO2012 / 162254, WO2010 / 116084).

[0633] The compound of formula (4) (wherein Q is as defined above) is commercially available or can be obtained by converting or derivatizing another compound of formula (4) according to well-known methods.

[0634] The compound of formula (10) can be prepared from the compound of formula (8) via steps comprising:[[]]

[0635] - Reacting the compound of formula (8) with a reagent of formula (4) in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (9).

[0636] - The compound of formula (9) (wherein A, Q, Y 1 、Y 2 、Y 3 and Y 4 are as defined above) is converted to the compound of formula (10) (WO2012 / 162254) in the presence of a halogenating reagent (such as POCl3, POBr3, PCl3 or PBr3).

[0637] The compound of formula (1-a1) can be prepared by subjecting the compound of formula (10) to the following treatment:[[]]

[0638] - A base (such as nBuLi) and carbon dioxide or a compound of formula (11), or

[0639] - Using carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0640] Method F

[0641] The compound of formula (1-a2) can be prepared by a method as shown in Scheme 6, the method comprising the step of reacting a compound of formula (14) with carbon monoxide, carbon dioxide or a reagent of formula (11), wherein Q and R in formula (1-a2) 7 are as defined above, and

[0642] A is N,

[0643] U 1 is hydroxy or C1-C6-alkoxy,

[0644] Y 5 、Y 6 and Y 7 are independently C-H, C-R 7 、O, S or NR7 ,

[0645] wherein

[0646] R 7 is as defined above,

[0647] wherein A, Q, and Y in formula (14) 5 , Y 6 and Y 7 are as defined above, and

[0648] X 6 is a halogen,

[0649] wherein E in formula (11)

[0650] E 2 is a halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy,

[0651] U 2 is C1-C6-alkoxy.

[0652]

[0653] The compound of formula (12) (wherein Y 5 , Y 6 and Y 7 are as defined above, and X 5 is a halogen) is commercially available or can be prepared according to the methods described in the literature (WO2017 / 133667; J. Org. Chem. 2004, 79, 10311-10322; Monatshefte für Chemie 1986, 117, 221-230).

[0654] The compound of formula (14) can be prepared from the compound of formula (12) by a process comprising the following steps:

[0655] - Reacting the compound of formula (12) with a reagent of formula (4) (wherein Q is as defined above) in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (13) (wherein A, Q, Y 5 , Y 6 and Y 7 are as defined above).

[0656] - Treating the compound of formula (13) with a halogenating reagent (such as bromide, iodide, NCS, NBS) in the presence of a base as described herein to form a compound of formula (14).

[0657] The compound of formula (1-a2) can be prepared by treating the compound of formula (14) as follows:

[0658] - An alkali (such as nBuLi) and carbon dioxide or a compound of formula (11), or

[0659] - Carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0660] Then, the resulting compound of formula (1-a2) can be further converted through one or more steps.

[0661] Non-limiting examples of such conversions are described below.

[0662] Method G

[0663] The compound of formula (1-b1) can be prepared by the method shown in Scheme 7, which comprises the step of reacting a compound of formula (17) with carbon monoxide, wherein Q in formula (1-b1) is as defined above, and

[0664] A is CR 8 ,

[0665] wherein

[0666] R 8 is as defined above,

[0667] Y 1 , Y 2 , Y 3 and Y 4 are independently C-H, C-R 7 or N,

[0668] wherein

[0669] R 7 is as defined above,

[0670] U 1 is hydroxy or C1-C6-alkoxy,

[0671] wherein A, Q, Y 1 , Y 2 , Y 3 and Y 4 in formula (17) are as defined above, and

[0672] X 8 is halogen.

[0673]

[0674]

[0675] The compound of formula (15) (wherein A, Y 1 , Y2 , Y 3 and Y 4 As defined above, X 7 is a halogen and W is hydrogen or benzyl) are commercially available or can be prepared according to the methods described in the literature (WO2017 / 023905; WO2017 / 112678; Monatshefte für Chemie 2018, 149, 1857 - 1864).

[0676] The compound of formula (4) (wherein Q is as defined above) is commercially available or can be obtained by converting or derivatizing another compound of formula (4) according to well - known methods.

[0677] The compound of formula (17) can be prepared from the compound of formula (15) via steps comprising:

[0678] - Reacting the compound of formula (15) with a reagent of formula (4) in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (16) (where A, Q, W, Y 1 , Y 2 , Y 3 and Y 4 are as defined above).

[0679] - When W is hydrogen, directly converting the compound of formula (16) into the compound of formula (17) in the presence of a dehydrating agent (such as POCl3, POBr3, PCl3 or PBr3).

[0680] - When W is benzyl, first performing a deprotection step to obtain the compound of formula (16, W = hydrogen), and then directly converting it into the compound of formula (17) in the presence of a dehydrating agent (such as POCl3, POBr3, PCl3 or PBr3).

[0681] The compound of formula (1 - b1) can be prepared by treating the compound of formula (17) with carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0682] Method H

[0683] The compound of formula (1 - b2) can be prepared by the method as shown in Scheme 8, which comprises the step of reacting the compound of formula (20) with carbon monoxide, wherein Q in formula (1 - b2) is as defined above, and

[0684] A is CR 8 ,

[0685] wherein

[0686] R 8As defined above,

[0687] Y 5 、Y 6 and Y 7 are independently C-H, C-R 7E 、C-R 7F 、C-R 7G 、O, S, N or N-R 7H ,

[0688] wherein

[0689] R 7E 、R 7F and R 7G are as defined above,

[0690] R 7H is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, -C(=O)R 21 or -C(=O)(OR 22 ),

[0691] wherein

[0692] R 21 is C1-C6-alkyl or C1-C6-haloalkyl,

[0693] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted with 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0694] R 22 is hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0695] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted with 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0696] provided that at least one of Y 5 、Y 6 and Y 7 is C-H, C-R 7E 、C-R 7F or C-R 7G ,

[0697] U 1is a hydroxyl group or a C1-C6-alkoxy group,

[0698] wherein A, Q, Y in formula (20) 5 , Y 6 and Y 7 are as defined above, and

[0699] X 11 is a halogen.

[0700]

[0701] The compound of formula (18) (wherein A, Y 5 , Y 6 and Y 7 are as defined above, X 10 is a halogen and W is hydrogen or benzyl) is commercially available or can be prepared according to the methods described in the literature (WO2005 / 095401; WO2018 / 067422; WO2016 / 106106; WO2014 / 144455; WO2013 / 086397).

[0702] The compound of formula (20) can be prepared from the compound of formula (18) by a step comprising:

[0703] - Reacting the compound of formula (18) with the reagent of formula (4) in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (19).

[0704] - When W is hydrogen, directly converting the compound of formula (19) (wherein A, Q, W, Y 5 , Y 6 and Y 7 are as defined above) into the compound of formula (20) in the presence of a dehydrating agent (such as POCl3, POBr3, PCl3 or PBr3).

[0705] - When W is benzyl, first performing a deprotection step to obtain the compound of formula (19, W = hydrogen), and then directly converting it into the compound of formula (20) in the presence of a dehydrating agent (such as POCl3, POBr3, PCl3 or PBr3).

[0706] The compound of formula (1-b2) can be prepared by treating the compound of formula (20) with carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0707] Method I

[0708] The compound of formula (1-c) can be prepared by the method as shown in Scheme 9, said method comprising reacting a compound of formula (24) (wherein p, A, Q, Y8 and R 7K a step of reacting with carbon dioxide or a reagent of formula (11), wherein p, Q and R in formula (1-c) 7K are as defined above, and

[0709] A is N,

[0710] U 1 is hydroxy or C1-C6-alkoxy,

[0711] Y 8 is O, S or NR 7KA ,

[0712] wherein

[0713] R 7KA is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, -C(=O)R 21 or -C(=O)(OR 22 ),

[0714] wherein, R 21 and R 22 are as defined above,

[0715] x 3 is 1, 2 or 3,

[0716] wherein, in formula (11)

[0717] E 3 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy,

[0718] U 2 is C1-C6-alkoxy.

[0719]

[0720]

[0721] Compounds of formulas (21) and (22) (wherein p, x 3 , A, Y 8 and R 7K are as defined above, and X 12 , X 13 and X 14 are halogen) are commercially available.

[0722] The compound of formula (4) (wherein Q is as defined above) is commercially available or can be obtained by converting or derivatizing another compound of formula (4) according to well-known methods.

[0723] The compound of formula (24) can be prepared from the compound of formula (21) by the steps comprising:

[0724] - Reacting the compound of formula (21) with the reagent of formula (22) in the presence of a base and optionally in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (23).

[0725] - Reacting the compound of formula (23) with the reagent of formula (4) in the presence of a base and a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (24).

[0726] The compound of formula (1-c) can be prepared by treating the compound of formula (24) with a base (such as nBuLi or lithium diisopropylamide) and carbon dioxide or the reagent of formula (11).

[0727] Method J

[0728] The compound of formula (1-d) can be prepared by the method as shown in Scheme 10, which method comprises the step of reacting a compound of formula (27) (wherein p, A, Q, Y 8 , R 7K and x 3 are as defined above) with carbon dioxide or the reagent of formula (11), wherein p, Q and R in formula (1-d) 7K are as defined above, and

[0729] A is C-R 8 ,

[0730] wherein R 8 is as defined above,

[0731] U 1 is hydroxy or C1-C6-alkoxy,

[0732] Y 8 is O, S or NR 7KA ,

[0733] wherein

[0734] R 7KA is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, -C(=O)R 21 or -C(=O)(OR 22 ),

[0735] wherein R 21 and R 22 are as defined above,

[0736] x 3 is 1 or 2,

[0737] Among them, in formula (11),

[0738] U 2 is C1-C6-alkoxy,

[0739] E 3 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy.

[0740]

[0741] The compounds of formulas (22) and (25) are commercially available.

[0742] The compound of formula (4) is commercially available or can be obtained by converting or derivatizing another compound of formula (4) according to well-known methods.

[0743] The compound of formula (27) can be prepared from the compound of formula (25) (where A is as defined above and Z 1 is hydroxy or halogen) by the following steps:

[0744] - Reacting the compound of formula (25) with the reagent of formula (22) (where p, x 3 and Y 8 are as defined above) in the presence of a base and optionally in the presence of a suitable transition metal catalyst salt or complex as described herein, and then by a halogenation step (e.g., with a bromide) to form a compound of formula (26) (where p, x 3 , A and Y 8 are as defined above and X 15 is halogen).

[0745] - Reacting the compound of formula (26) with the reagent of formula (4) in the presence of a suitable transition metal catalyst salt or complex as described herein to form the compound of formula (27).

[0746] The compound of formula (1-d) can be prepared by treating the compound of formula (27) with a base (such as nBuLi or lithium diisopropylamide) and carbon dioxide or the reagent of formula (11).

[0747] Method K

[0748] The compound of formula (1-e) can be prepared by the method as shown in Scheme 11, which comprises reacting the compound of formula (28) with the reagent of formula (6) in the presence of a metal photoredox catalyst and a base (such as an organic or inorganic base) as described herein, where p, Q and R in formula (1-e) 7K are as defined above and

[0749] A is N,

[0750] Y 1 is C-H, C-R 7K , O, S or S(=O)2,

[0751] wherein R 7K is as defined above,

[0752] U 1 is C1-C6-alkoxy,

[0753] x 1 is 1 or 2,

[0754] x 2 is 0, 1 or 2,

[0755] wherein A, Q, and U in formula (28) 1 are as defined above, and

[0756] X 16 is halogen,

[0757] wherein p, x in formula (6) 1 , Y 1 and R 7K are as defined above.

[0758]

[0759] Method K can be carried out under the same conditions as Method C.

[0760] The compound of formula (28) can be prepared by Method M described herein.

[0761] Method L

[0762] The compound of formula (1-f) can be prepared by a method comprising the step of reacting a compound of formula (33) with a reagent of formula (4) in the presence of a base (such as an organic or inorganic base), optionally in the presence of a suitable transition metal catalyst salt or complex described herein, wherein p, Q and R in formula (1-f) 7 are as defined above, and

[0763] A is N,

[0764] Y is a 5- to 8-membered saturated or partially saturated carbocyclic group or a 5- to 8-membered saturated or partially saturated heterocyclic group fused to a pyridine ring / pyridazine ring,

[0765] U 1 is C1-C6-alkoxy,

[0766] wherein p, A, Q, Y, U in formula (33) 1 and R 7 are as defined above, and

[0767] X 17 is a halogen,

[0768] wherein Q in formula (4) is as defined above.

[0769]

[0770] The compound of formula (33) can be prepared from the compound of formula (32) (wherein p, A, Y, U 1 and R 7 are as defined above) in the presence of a halogenating reagent such as POCl3, POBr3, PCl3 or PBr3.

[0771] The compound of formula (32) can be prepared from the compound of formula (29) and the compound of formula (30) according to the method described in the literature (WO2018 / 125800).

[0772] The compounds of formula (29) and formula (30) are commercially available.

[0773] wherein U 1 is C1-C6-alkoxy of the compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f) can be converted to the compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f) wherein U 1 is hydroxyl by a well-known functional group interconversion method (e.g., by hydrolyzing the ester group with LiOH in tetrahydrofuran / water).

[0774] wherein U 1 is hydroxyl of the compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f) can be converted to the compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f) wherein U 1 is a halogen by a well-known method in the presence of a halogenating reagent. Suitable halogenating reagents include but are not limited to phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride or thionyl chloride.

[0775] Process for preparing a compound of formula (5)

[0776] Method M

[0777] The compound of formula (5) (wherein m, n, A, Q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and X2 (as defined in Process D) can be prepared by the process as shown in Scheme 13, said process comprising the step of reacting a compound of formula (28) with an amine of formula (2) or a salt thereof, wherein A, Q and X in formula (28) 2 are as defined above, and

[0778] U 1 is C1-C6-alkoxy,

[0779] X 18 is halogen,

[0780] wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 in formula (2) are as defined above.

[0781]

[0782] Process M can be carried out using reaction conditions similar to those described for Process A.

[0783] The compound of formula (28) can be prepared by reacting a compound of formula (34) with a reagent of formula (4) (wherein Q is as defined above) in the presence of a base and optionally in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0784] The compound of formula (34) is commercially available.

[0785] The compound of formula (4) is commercially available or can be obtained by converting or derivatizing another compound of formula (4) according to well-known methods.

[0786] wherein U 1 is C1-C6-alkoxy can be converted to a compound of formula (28) wherein U 1 is hydroxy by well-known functional group interconversion methods (for example, by hydrolyzing the ester group with LiOH in tetrahydrofuran / water).

[0787] wherein U 1 is hydroxy can be converted to a compound of formula (28) wherein U 1 is halogen by well-known methods in the presence of a halogenating reagent. Suitable halogenating reagents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride or thionyl chloride.

[0788] Process for preparing a compound of formula (3)

[0789] Process N

[0790] The compound of formula (3) can be prepared by the method shown in Scheme 14, which comprises the step of reacting a compound of formula (36) with an amine of formula (2) or a salt thereof, wherein m, n, p, A, Y, R in formula (3) 2 , R 3 , R 4 , R 5 , R 6 and R 7 are as defined above, and

[0791] X 1 is a halogen,[[]]END]]

[0792] wherein p, A, Y, X in formula (36) 1 and R 7 are as defined above, and

[0793] U 1 is a hydroxyl group or a C1-C6-alkoxy group,[[]]END]]

[0794] wherein m, n, R in formula (2) 2 , R 3 , R 4 , R 5 and R 6 are as defined above.[[]]END]]

[0795]

[0796] Method N can be carried out using reaction conditions similar to those described for Method A.[[]]END]]

[0797] The compound of formula (36) can be prepared by treating a compound of formula (35) (wherein p, A, Y, X 1 and R 7 are as defined above, and G is hydrogen, a halogen, methanesulfonyloxy, trifluoromethanesulfonyloxy or p-toluenesulfonyloxy) as follows:

[0798] - a base (e.g., nBuLi when G is a halogen, or lithium diisopropylamide when G = H) and carbon dioxide or a reagent of formula (11), or

[0799] - in the presence of a suitable transition metal catalyst salt or complex described herein, using carbon monoxide and an alcohol (when G is a halogen, methanesulfonyloxy, trifluoromethanesulfonyloxy or p-toluenesulfonyloxy).

[0800] The compound of formula (35) is commercially available or can be prepared according to the methods described in the literature (WO2017 / 004500; WO2017 / 112719; WO2016 / 115272; WO2011 / 015343; WO2017 / 023905; WO2017 / 112678; Monatshefte für Chemie 2018, 149, 1857-1864; WO2005 / 095401; WO2018 / 067422; WO2016 / 106106; WO2014 / 144455; WO2013 / 086397; WO2014 / 0121198; WO2011 / 145287; WO2012 / 098387; Eur. J. Med. Chem. 2017, 138, 816-829).

[0801] The compounds according to the invention can be prepared according to the above methods. However, it should be understood that based on his common knowledge and the available publications, a person skilled in the art will be able to modify these methods according to the specific circumstances of each compound of the invention to be synthesized as desired.

[0802] Intermediates for preparing a compound of formula (I)

[0803] The present invention also relates to intermediates for the preparation of the compounds of formula (I).

[0804] Accordingly, the present invention relates to compounds of formula (1):

[0805]

[0806] wherein

[0807] A is N or CR 8 ,

[0808] wherein

[0809] R 8 is hydrogen, halogen, cyano or C1-C4-alkyl,

[0810] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[0811] Ring Y together with the pyridine ring or the pyridazine ring forms a bicyclic heterocyclic group or a bicyclic heteroaryl group,

[0812] provided that the resulting bicyclic heteroaryl is not quinoline,

[0813] P is 0, 1, 2, 3 or 4,

[0814] R 7is halogen, cyano, nitro, hydroxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2,

[0815] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl are optionally substituted by 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0816] wherein the C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0817] and wherein

[0818] R 20 is independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0819] wherein the C1-C6-alkyl is optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0820] and

[0821] wherein the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0822] R 21 、R 22 、R 23 and R 24 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0823] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0824] or, wherein

[0825] two substituents R 7 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0826] Q is C6-C 14 -aryl, C3-C 12 -carbocyclic group, a 3- to 14-membered heterocyclic group or a 5- to 14-membered heteroaryl group,

[0827] wherein the C6-C 14 -aryl, C3-C 12 -carbocyclic group, a 3- to 14-membered heterocyclic group and a 5- to 14-membered heteroaryl group are optionally substituted by 1 to 5 substituents independently selected from the following Q SSubstituents: halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkoxycarbon ... C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 、-NR 26 C(=O)R 27 、-C(=O)N(R 28 )2, -C(=S)R 29 、-C(=S)N(R 30 )2, -C(=NR 31 )R 32 、-C(=NOR 33 )R 34 and -N(R 35 )2,

[0828] in

[0829] The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6 -alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and -Si(C1-C6-alkyl)3 are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,

[0830] The C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclyl,

[0831] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3 to 7-membered heterocyclic group are optionally substituted in turn by two substituents, and the two substituents together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl group,

[0832] R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34

[0833] are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0834] wherein

[0835] the C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0836] and, wherein

[0837] R 35 is independently hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl,

[0838] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group, wherein the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic group,

[0839] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are each optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0840] and its N-oxides, salts, solvates and solvates of its salts and N-oxides.

[0841] Accordingly, similarly, the present invention also relates to a compound of formula (1):

[0842]

[0843] wherein

[0844] A is N or CR 8 ,

[0845] wherein

[0846] R 8 is hydrogen, halogen or C1-C4-alkyl,

[0847] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[0848] ring Y together with the pyridine ring or pyridazine ring forms a bicyclic heterocyclic group or bicyclic heteroaryl group,

[0849] with the proviso that the resulting bicyclic heteroaryl group is not quinoline,

[0850] P is 0, 1, 2, 3 or 4,

[0851] R 7 is halogen, cyano, nitro, hydroxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2,

[0852] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl are optionally substituted by 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0853] Among them, C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted by 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0854] And, among them

[0855] R 20 is independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0856] Among them, C1-C6-alkyl is optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0857] And

[0858] Among them, C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0859] R 21 、R 22 、R 23 and R 24 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0860] Among them, C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0861] Or, among them

[0862] Two substituents R 7Together with the carbon atoms to which they are attached, form a C3-C8-cycloalkyl-ring,

[0863] Q is C6-C 14 -aryl, C3-C 12 -carbocyclic group, 3- to 14-membered heterocyclic group or 5- to 14-membered heteroaryl group,

[0864] wherein the C6-C 14 -aryl, C3-C 12 -carbocyclic group, 3- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl group are optionally substituted by 1 to 5 substituents independently selected from the following Q S substituents: halogen, cyano, isocyano, nitro, hydroxy, mercapto, formyl, carboxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclic group, 5- to 14-membered heteroaryl group, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, -O-C(=O)R 25 、-NR 26 C(=O)R 27 、-C(=O)N(R 28 )2、-C(=S)R 29 、-C(=S)N(R 30 )2、-C(=NR 31 )R 32 、-C(=NOR 33 )R 34 and -N(R 35 )2,

[0865] wherein

[0866] The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6 -alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and -Si(C1-C6-alkyl)3 are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,

[0867] The C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclyl,

[0868] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3 to 7-membered heterocyclic group are optionally substituted in turn by two substituents, and the two substituents together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl group,

[0869] R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34

[0870] are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0871] wherein

[0872] the C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0873] and, wherein

[0874] R 35 is hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl,

[0875] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group, wherein the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic group,

[0876] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are each optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0877] and their N-oxides, salts, solvates and solvates of their salts and N-oxides.

[0878] Accordingly, the present invention also relates to a compound of formula (1):

[0879]

[0880] Among them

[0881] A is CR 8 ,

[0882] Among them

[0883] R 8 is hydrogen, halogen, cyano or C1-C4-alkyl,

[0884] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[0885] Ring Y and the pyridine ring together form a quinoline ring,

[0886] P is 0, 1, 2, 3 or 4,

[0887] R 7 is halogen, cyano, nitro, hydroxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 )、-C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2,

[0888] wherein, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0889] Wherein, C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0890] And, wherein

[0891] R 20 is independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0892] Wherein, C1-C6-alkyl is optionally substituted with 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0893] And

[0894] Wherein, C3-C8-cycloalkyl is optionally substituted with 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0895] R 21 、R 22 、R 23 and R 24 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0896] Wherein, C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted with 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0897] Q is phenyl,

[0898] Wherein, phenyl is optionally substituted with 1 to 5 Qs independently selected from the following SSubstituents: halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkoxycarbon ... C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 、-NR 26 C(=O)R 27 、-C(=O)N(R 28 )2, -C(=S)R 29 、-C(=S)N(R 30 )2, -C(=NR 31 )R 32 、-C(=NOR 33 )R 34 and -N(R 35 )2,

[0899] in

[0900] The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and –Si(C1-C6-alkyl)3 are optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic groups,

[0901] The C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclic group and 5- to 14-membered heteroaryl are optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic groups,

[0902] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are each optionally substituted by two substituents which, together with the carbon atom to which they are attached, form a C3-C8-cycloalkyl,

[0903] R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 and R 34

[0904] are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0905] wherein

[0906] the C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0907] and, wherein

[0908] R 35 is hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl,

[0909] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group, wherein the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from the following: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic group,

[0910] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are each optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0911] and their N-oxides, salts, solvates and solvates of their salts and N-oxides.

[0912] Accordingly, similarly, the present invention also relates to a compound of formula (1):

[0913]

[0914] wherein

[0915] A is CR 8 ,

[0916] wherein

[0917] R 8 is hydrogen, halogen or C1-C4-alkyl,

[0918] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[0919] ring Y and the pyridine ring together form a quinoline ring,

[0920] P is 0, 1, 2, 3 or 4,

[0921] R 7 is halogen, cyano, nitro, hydroxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2,

[0922] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl are optionally substituted by 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0923] Among them, the C3-C8-cycloalkyl group and the C3-C8-cycloalkenyl group are optionally substituted with 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl,

[0924] and, among them

[0925] R 20 is independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl,

[0926] Among them, the C1-C6-alkyl group is optionally substituted with 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl,

[0927] and

[0928] Among them, the C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl,

[0929] R 21 R 22 R 23 and R 24 are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl,

[0930] Among them, the C1-C6-alkyl group and the C1-C6-haloalkyl group are optionally substituted with 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl,

[0931] Q is phenyl,

[0932] Among them, the phenyl group is optionally substituted with 1 to 5 Qs independently selected from the following SSubstituents: halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkoxycarbon ... C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 、-NR 26 C(=O)R 27 、-C(=O)N(R 28 )2, -C(=S)R 29 、-C(=S)N(R 30 )2, -C(=NR 31 )R 32 、-C(=NOR 33 )R 34 and -N(R 35 )2,

[0933] in

[0934] The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6 -alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and -Si(C1-C6-alkyl)3 are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,

[0935] The C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclyl,

[0936] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3 to 7-membered heterocyclic group are optionally substituted in sequence by two substituents, and the two substituents together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl group,

[0937] R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 and R 34

[0938] are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0939] wherein

[0940] the C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy are each optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0941] and, wherein

[0942] R 35 is hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl,

[0943] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are each optionally substituted by 1 to 3 substituents independently selected from: cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, –Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0944] wherein the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl and 3- to 7-membered heterocyclic group,

[0945] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are each optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0946] and their N-oxides, salts, solvates and solvates of their salts and N-oxides.

[0947] The present invention relates to a compound of formula (3):

[0948]

[0949] wherein

[0950] X 1 is a halogen,

[0951] T is O,

[0952] n is 1,

[0953] m is 1,

[0954] A is N or CR 8 ,

[0955] wherein

[0956] R 8 is hydrogen, a halogen, a cyano group or a C1-C4-alkyl group,

[0957] R 1 is hydrogen, a hydroxyl group, a cyano group, a C1-C6-alkyl group, a C1-C6-alkoxy group, -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 , -S(=O)2R 12 , -C(=O)N(R 13 )2 or -S(=O)2N(R 14 ),

[0958] wherein

[0959] R 10 , R 11 and R 12 are independently a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C3-C8-cycloalkyl group or a C2-C6-alkenyl group,

[0960] R 13 and R 14 are independently hydrogen, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C3-C8-cycloalkyl group or a C2-C6-alkenyl group,

[0961] R 2 and R 3 are independently hydrogen,

[0962] R 4 and R 5 are independently hydrogen or fluorine,

[0963] R 6 is a C3-C 12 -carbocyclic group, a C6-C 14 -aryl group, a 3- to 14-membered heterocyclic group, a 5- to 14-membered heteroaryl group, a C3-C 12 -carbocyclic group oxy, a C6-C14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C1-C3-alkoxy or C1-C3-haloalkoxy, wherein the C1-C3-alkoxy and C1-C3-haloalkoxy are each independently substituted by a substituent selected from: C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl,

[0964] wherein the C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl are each independently optionally substituted by 1 to 4 R 6S substituents, wherein the C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclic group oxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy and 3- to 14-membered heterocyclyloxy are each independently optionally substituted by 1 to 4 R 6S substituents,

[0965] wherein

[0966] R 6S is independently halogen, cyano, isocyano, nitro, hydroxy, oxo, mercapto, pentafluorothio, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 15 )2, -C(=O)R 16 , -C(=O)(OR 17 ), -C(=O)N(R 18 )2, -S(=O)2N(R 19 )2, -O-Si(C1-C6-alkyl)3 or –Si(C1-C6-alkyl)3,

[0967] Wherein, the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and –Si(C1-C6-alkyl)3 are further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group,

[0968] and

[0969] Wherein, the C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are further optionally substituted by 1 to 4 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0970] or

[0971] Two C1-C6-alkyl substituents connected to the same carbon atom form a C3-C8-cycloalkyl-ring,

[0972] or

[0973] Two R 6S substituents optionally form a C3-C8-cycloalkyl-ring together with the carbon atom to which they are attached,

[0974] and, wherein

[0975] R 15 is independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0976] Wherein, the C1-C6-alkyl is further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclic group,

[0977] and

[0978] Wherein, the C3-C8-cycloalkyl is further optionally substituted by 1 to 4 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl,

[0979] R 16 、R 17 、R 18 and R 19 are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl,

[0980] Wherein, the C1-C6-alkyl or C1-C6-haloalkyl is further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclic group,

[0981] Ring Y together with the pyridine ring or pyridazine ring forms a bicyclic heterocyclic group or bicyclic heteroaryl,

[0982] P is 0, 1, 2, 3, or 4,

[0983] R 7 is halogen, cyano, nitro, hydroxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R21 , -C(=O)(OR 22 ) , -C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2,

[0984] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl are optionally substituted by 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0985] wherein the C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted by 1 to 3 substituents independently selected from: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0986] and, wherein

[0987] R 20 is independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0988] wherein the C1-C6-alkyl is optionally substituted by 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0989] and

[0990] Wherein, the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0991] R 21 、R 22 、R 23 and R 24 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0992] Wherein, the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[0993] Alternatively, wherein

[0994] two substituents R 7 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0995] and its N-oxides, salts, solvates and solvates of its salts and N-oxides.

[0996] Similarly, the present invention relates to a compound of formula (3):

[0997]

[0998] Wherein

[0999] X 1 is halogen,

[1000] T is O,

[1001] n is 1,

[1002] m is 1,

[1003] A is N or CR 8 ,

[1004] Wherein

[1005] R 8 is hydrogen or halogen,

[1006] R 1is hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 , -S(=O)2R 12 , -C(=O)N(R 13 )2 or -S(=O)2N(R 14 )2,

[1007] wherein

[1008] R 10 , R 11 and R 12 are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[1009] R 13 and R 14 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[1010] R 2 and R 3 are independently hydrogen,

[1011] R 4 and R 5 are independently hydrogen or fluorine,

[1012] R 6 is C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclic group oxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclic group oxy, C1-C3-alkoxy or C1-C3-haloalkoxy, wherein the C1-C3-alkoxy and C1-C3-haloalkoxy are independently substituted by a substituent selected from the following: C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl,

[1013] wherein, the C3-C 12 -carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl are each optionally substituted by 1 to 4 R 6S substituents,

[1014] wherein, C3-C 12-carbocyclic group, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclic oxy group, C6-C 14 -aryloxy group, 5- to 14-membered heteroaryloxy group and 3- to 14-membered heterocyclic oxy group are optionally substituted with 1 to 4 R 6S substituents,

[1015] wherein

[1016] R 6S is independently halogen, cyano, isocyano, nitro, hydroxy, oxo, mercapto, pentafluorothio, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 15 )2, -C(=O)R 16 , -C(=O)(OR 17 )), -C(=O)N(R 18 )2, -S(=O)2N(R 19 )2, -O-Si(C1-C6-alkyl)3 or –Si(C1-C6-alkyl)3,

[1017] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and –Si(C1-C6-alkyl)3 are further optionally substituted by 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group, and

[1018] wherein the C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are further optionally substituted by 1 to 4 substituents independently selected from: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[1019] or

[1020] two C1-C6-alkyl substituents attached to the same carbon atom form a C3-C8-cycloalkyl-ring,

[1021] or

[1022] two R 6S substituents optionally together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[1023] and, wherein

[1024] R 15 is hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[1025] Wherein, the C1-C6-alkyl is further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group,

[1026] and

[1027] Wherein, the C3-C8-cycloalkyl is further optionally substituted by 1 to 4 substituents independently selected from the following: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[1028] R 16 、R 17 、R 18 and R 19 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[1029] Wherein, the C1-C6-alkyl or C1-C6-haloalkyl is further optionally substituted by 1 to 3 substituents independently selected from the following: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, –Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group,

[1030] Ring Y together with the pyridine ring or pyridazine ring forms a bicyclic heterocyclic group or bicyclic heteroaryl group,

[1031] P is 0, 1, 2, 3 or 4,

[1032] R 7 is halogen, cyano, nitro, hydroxy, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R21 ,-C(=O)(OR 22 ),-C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2,

[1033] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl are optionally substituted with 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[1034] wherein C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from: halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[1035] and, wherein

[1036] R 20 is independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[1037] wherein C1-C6-alkyl is optionally substituted with 1 to 3 substituents independently selected from: cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[1038] and

[1039] wherein the C3-C8-cycloalkyl is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[1040] R 21 , R 22 , R 23 and R 24 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[1041] wherein C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted by 1 to 3 substituents independently selected from the group consisting of cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl and C3-C8-halocycloalkyl,

[1042] or, where

[1043] Two substituents R 7 Together with the carbon atom to which they are attached they form a C3-C8-cycloalkyl-ring,

[1044] and N-oxides, salts, solvates thereof and solvates of their salts and N-oxides.

[1045] The present invention also relates to an intermediate of formula (4):

[1046] Q-OH(4),

[1047] in

[1048] Q is a group of the formula:

[1049]

[1050] §2 connected with OH,

[1051] Q S1 For fluorine,

[1052] Q S2 is C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl or C3-C6-halocycloalkyl,

[1053] Provided that the compound of formula (4) is not:

[1054] 1-(2-Fluoro-3-hydroxyphenyl)cyclopropanecarboxylic acid 1507131-96-5

[1055] 2-Fluoro-3-(prop-1-en-2-yl)phenol 1375066-38-8

[1056] 3-Cyclopropyl-2-fluorophenol 2290421-25-7

[1057] 2-Fluoro-3-(1-fluorocyclopropyl)phenol 2385918-06-7

[1058] 3-(2,2-Difluorocyclopropyl)-2-fluorophenol 2435608-24-3

[1059] 2-Fluoro-3-vinylphenol 2290411-18-4

[1060] 2-Fluoro-3-[(E)-prop-1-enyl]phenol 2435608-23-2

[1061] 2-Fluoro-3-isopropenylphenol 1375066-38-8

[1062] 3-(2,2-Difluorocyclopropyl)-2-fluorophenol 2435608-24-3

[1063] The present invention also relates to an intermediate of formula (4):

[1064] Q-OH (4),

[1065] wherein

[1066] Q is a group of the following formula:

[1067]

[1068] §2 is connected to OH,

[1069] Q S1 is fluorine,

[1070] Q S2 is C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl or C3-C6-halocycloalkyl,

[1071] provided that the compound of formula (4) is not:

[1072] 2-Fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)phenol 2168012-00-6

[1073] 3-(1-Ethoxyvinyl)-2-fluorophenol 2137960-04-2

[1074] 1-(2-Fluoro-3-hydroxyphenyl)cyclopropanecarbonitrile 1881320-49-5

[1075] 3-(1-Aminocyclopropyl)-2-fluorophenol 1785193-75-0

[1076] 1-(2-Fluoro-3-hydroxyphenyl)cyclopropanecarboxylic acid 1507131-96-5

[1077] 2-Fluoro-3-(prop-1-en-2-yl)phenol 1375066-38-8

[1078] 3-Cyclopropyl-2-fluorophenol 2290421-25-7

[1079] 2-Fluoro-3-(1-fluorocyclopropyl)phenol 2385918-06-7

[1080] 3-(2,2-Difluorocyclopropyl)-2-fluorophenol 2435608-24-3

[1081] 2-Fluoro-3-ethenylphenol 2290411-18-4

[1082] 2-Fluoro-3-[(E)-prop-1-enyl]phenol 2435608-23-2

[1083] 2-Fluoro-3-isopropenylphenol 1375066-38-8

[1084] 3-(2,2-Difluorocyclopropyl)-2-fluorophenol 2435608-24-3

[1085] Compositions and formulations

[1086] The present invention further relates to compositions, in particular compositions for controlling unwanted microorganisms. The compositions can be applied to the microorganisms and / or their habitats.

[1087] Said Composition comprises at least one compound of formula (I) and at least one agriculturally suitable adjuvant, such as a carrier and / or a surfactant.

[1088] Carrieris a solid or liquid, natural or synthetic, organic or inorganic substance that is usually inert. The carrier generally enables better application of the compound 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, palygorskite, montmorillonite and diatomaceous earth; silica gel and synthetic rock powders such as finely divided silica, alumina and silicates. Examples of typically useful solid carriers for preparing granulates include, but are not limited to: crushed and classified natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic powders, and granules of organic materials such as paper, sawdust, coconut husks, corn cobs and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to: water, organic solvents and their combinations. Examples of suitable solvents include polar and non-polar organic chemical liquids, such as aromatic and non-aromatic hydrocarbons (e.g., cyclohexane, alkanes, alkylbenzenes, xylenes, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or dichloromethane), alcohols or polyols (which may optionally be substituted, etherified and / or esterified, e.g., ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or ethylene glycol), ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, their amides (e.g., dimethylformamide or fatty acid amides) and esters, lactams (e.g., N-alkylpyrrolidones, especially N-methylpyrrolidone) and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide), vegetable oils or oils derived from animals. The carrier can also be a liquefied gas extender, i.e., a liquid that is gaseous at standard temperature and standard pressure, such as aerosol propellants like halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.

[1089] Preferred solid carriers are selected from clay, talc and silica.

[1090] Preferred liquid carriers are selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams and carbonates.

[1091] The amount of the carrier is usually 1 to 99.99%, preferably 5 to 99.9%, more preferably 10 to 99.5%, most preferably 20 to 99%, based on the weight of the composition.

[1092] The liquid carrier is usually present in an amount of 20 to 99%, such as 30 to 80%, based on the weight of the composition.

[1093] The solid carrier is usually present in an amount of 0 to 50%, preferably 5 to 45%, such as 10 to 30%, based on the weight of the composition.

[1094] If the composition comprises more than two carriers, the above ranges refer to the total amount of the carriers.

[1095] 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, lignosulfonates (such as sodium lignosulfonate), phenolsulfonates or naphthalenesulfonates, condensates of ethylene oxide and / or propylene oxide with fatty alcohols, fatty acids or fatty amines (such as polyoxyethylene fatty acid esters, such as castor oil ethoxylate; polyoxyethylene fatty alcohol ethers, such as alkylaryl polyethylene glycol ethers), substituted phenols (preferably alkylphenols or arylphenols) and their ethoxylates (such as triphenylvinylphenol ethoxylate), salts of sulfosuccinates, taurine derivatives (preferably alkyl taurates), phosphates of polyethoxylated alcohols or phenols, fatty esters of polyols (such as fatty acid esters of glycerol, sorbitol or sucrose), sulfates (such as alkyl sulfates and alkyl ether sulfates), sulfonates (such as alkyl sulfonates, aryl sulfonates and alkylbenzene sulfonates), phosphates, protein hydrolysates, lignosulfate waste liquor and methylcellulose. Any salts mentioned in this paragraph preferably refer to their respective alkali metal salts, alkaline earth metal salts and ammonium salts.

[1096] Preferred surfactants are selected from polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, alkylbenzene sulfonates, such as calcium dodecylbenzenesulfonate, castor oil ethoxylate, sodium lignosulfonate and arylphenol ethoxylates, such as triphenylvinylphenol ethoxylate.

[1097] The amount of surfactant is usually 5 to 40%, such as 10 to 20%, based on the weight of the composition.

[1098] Suitable auxiliariesOther examples include water repellents, desiccants, adhesives (adhesives, tackifiers, fixatives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latexes (such as gum arabic, polyvinyl alcohol and polyvinyl acetate), natural phospholipids (such as cephalin and lecithin) and synthetic phospholipids, polyvinylpyrrolidone and sodium carboxymethylglycolate), thickeners and secondary thickeners (such as cellulose ethers, acrylic derivatives, xanthan gum, modified clays, such as available products named Bentone, and finely divided silica), stabilizers (such as cold stabilizers, preservatives (such as dichlorobenzene and benzyl alcohol hemiacetal), antioxidants, light stabilizers (especially UV stabilizers) or other reagents that can improve chemical and / or physical stability), dyes or pigments (such as inorganic pigments, such as iron oxide, titanium oxide and Prussian blue; organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes), defoamers (such as silicone defoamers and magnesium stearate), antifreeze agents, tackifiers, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including micronutrients, 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 complexing agents).

[1099] The choice of adjuvant is related to the intended mode of application of the compound of formula (I) and / or the physical properties of the compound. In addition, the adjuvant can be selected to impart specific properties (technical, physical and / or biological properties) to the composition or the use form prepared therefrom. The choice of adjuvant can allow the composition to be customized according to specific needs.

[1100] The composition of the present invention can be provided to the end user in the form of a ready-to-use formulation, i.e., a composition that can be directly applied to plants or seeds by means of a suitable device such as a spraying or dusting device. Alternatively, the composition can be provided to the end user in the form of a concentrate, which must be diluted before use, preferably with water.

[1101] The composition of the present invention can be prepared in a conventional manner, for example by mixing the compound of formula (I) with one or more suitable adjuvants (such as those disclosed above).

[1102] The composition contains a fungicidally effective amount of a compound of formula (I). The term "effective amount" means an amount sufficient to control harmful fungi on cultivated plants or to protect materials, and which does not cause substantial damage to the treated plants. Such amounts can vary within a wide range and depend on various factors such as the type of fungi to be controlled, the cultivated plants or materials to be treated, the climatic conditions and the particular compound of formula (I) used. Generally, the composition according to the invention contains from 0.01 to 99% by weight, preferably from 0.05 to 98% by weight, more preferably from 0.1 to 95% by weight, even more preferably from 0.5 to 90% by weight, most preferably from 1 to 80% by weight of the compound of formula (I). The composition may contain more than two compounds according to the invention. In this case, the above ranges refer to the total amount of the compounds according to the invention.

[1103] The composition according to the invention can be of any conventional Composition form , 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, broadcast granules), suspoemulsion concentrates, natural or synthetic products impregnated with the compound of formula (I), fertilizers and microcapsules in polymeric substances. The compound of formula (I) can be present in suspended, emulsified or dissolved form. Examples of particularly suitable forms of the composition 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), capsule suspensions (such as CS, ZC), pastes, tablets, wettable powders or dusts (such as WP, SP, WS, DP, DS), tablets (such as BR, TB, DT), granules (such as WG, SG, GR, FG, GG, MG), pesticidal articles (such as LN) and gel preparations (such as GW, GF) for treating plant propagation materials such as seeds. These and other composition types are defined by the Food and Agriculture Organization of the United Nations (FAO). A review of the given can be found in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th edition, May 2008, CropLife International.

[1104] Preferably, the composition according to the invention is in the form of one of the following types: EC, SC, FS, SE, OD and WG, more preferably EC, SC, OD and WG.

[1105] Further details of examples of composition types and their preparation are given below. If there are more than two compounds of the invention, the total amount of the compounds of the invention refers to the total amount of the compounds of the invention. This is with reference to any other components applicable to the composition, if there are more than two such components (e.g., wetting agents, binders).

[1106] i) Water-soluble concentrates (SL, LS)

[1107] 10 - 60% by weight of at least one compound of formula (I) and 5 - 15% by weight of a surfactant (e.g., polyoxyethylene fatty alcohol ether) are dissolved in a corresponding amount of water and / or water-soluble solvent (e.g., alcohol such as propylene glycol, or carbonate such as propylene carbonate) to obtain a total amount of 100% by weight. The concentrate is diluted with water before application.

[1108] ii) Dispersible concentrates (DC)

[1109] 5 - 25% by weight of at least one compound of formula (I) and 1 - 10% by weight of a surfactant and / or binder (e.g., polyvinylpyrrolidone) are dissolved in a corresponding amount of an organic solvent (e.g., cyclohexanone) to obtain a total amount of 100% by weight. A dispersant is obtained by dilution with water.

[1110] iii) Emulsifiable concentrates (EC)

[1111] 15 - 70% by weight of at least one compound of formula (I) 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., aromatic hydrocarbon or fatty acid amide), and if necessary, a water-soluble solvent is added to obtain a total amount of 100% by weight. An emulsion is obtained by dilution with water.

[1112] iv) Emulsions (EW, EO, ES)

[1113] 5 - 40% by weight of at least one compound of formula (I) and 1 - 10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 - 40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon). The mixture is added to a corresponding amount of water by an emulsifier to obtain a total amount of 100% by weight. The resulting composition is a homogeneous emulsion. The emulsion can be further diluted with water before application.

[1114] v) Suspension agents and suspension concentrates

[1115] v-1) Water-based (SC, FS)

[1116] In a suitable grinding device (such as a stirred ball mill), 20 - 60% by weight of at least one compound of formula (I) is pulverized with 2 - 10% by weight of a surfactant added (such as sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1 - 2% by weight of a thickener (such as xanthan gum) and water to obtain a fine suspension of the active substance. Water is added in an appropriate amount to make the total amount 100% by weight. The stable suspension of the active substance is obtained by diluting with water. For FS-type compositions, up to 40% by weight of a binder (such as polyvinyl alcohol) is added.

[1117] v-2) Oil-based (OD, OF)

[1118] In a suitable grinding device (such as a stirred ball mill), 20 - 60% by weight of at least one compound of formula (I) is ground with 2 - 10% by weight of a surfactant added (such as sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1 - 2% by weight of a thickener (such as modified clay, especially Bentone or silica) and an organic carrier to obtain a fine oil suspension of the active substance. The organic carrier is added in an appropriate amount to make the total amount 100% by weight. The stable dispersant of the active substance is obtained by diluting with water.

[1119] vi) Water-dispersible granules and water-soluble granules (WG, SG)

[1120] 50 - 80% by weight of at least one compound of formula (I) is finely ground with a surfactant added (such as sodium lignosulfonate and polyoxyethylene fatty alcohol ether) and is converted into water-dispersible or water-soluble granules by technical equipment (such as extrusion, spray tower, fluidized bed). The surfactant is used in an appropriate amount to make the total amount 100% by weight. The stable dispersant or solution of the active substance is obtained by diluting with water.

[1121] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[1122] In a rotor-stator mill, 50 - 80% by weight of at least one compound of formula (I) is finely ground with 1 - 8% by weight of a surfactant added (such as sodium lignosulfonate, polyoxyethylene fatty alcohol ether) and an appropriate amount of a solid carrier (such as silica gel) to make the total amount 100% by weight. The stable dispersant or solution of the active substance is obtained by diluting with water.

[1123] viii) Gels (GW, GF)

[1124] In a stirred ball mill, 5 - 25% by weight of at least one compound of formula (I) is comminuted with 3 - 10% by weight of a surfactant added (such as sodium lignosulfonate), 1 - 5% by weight of a binder (such as carboxymethyl cellulose) and the corresponding amount of water to give a total of 100% by weight. This results in a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[1125] ix) Microemulsion (ME)

[1126] 5 - 20% by weight of at least one compound of formula (I) is added to 5 - 30% by weight of an organic solvent mixture (such as fatty acid dimethylamide and cyclohexanone), 10 - 25% by weight of a surfactant mixture (such as polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and the corresponding amount of water to give a total of 100% by weight. The mixture is stirred for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[1127] x) Capsule suspension (CS)

[1128] An oil phase comprising 5 - 50% by weight of at least one compound of formula (I), 0 - 40% by weight of a water-insoluble organic solvent (such as aromatic hydrocarbons), 2 - 15% by weight of an acrylic monomer (such as methyl methacrylate, methacrylic acid and diacrylate or triacrylate) is dispersed in an aqueous solution of a protective colloid (such as polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate capsule suspensions. Alternatively, an oil phase comprising 5 - 50% by weight of at least one compound of formula (I), 0 - 40% by weight of a water-insoluble organic solvent (such as aromatic hydrocarbons) and an isocyanate monomer (such as diphenylmethylene - 4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (such as polyvinyl alcohol). Addition of a polyamine (such as hexamethylenediamine) results in the formation of a polyurea capsule suspension. The monomer amount is 1 - 10% by weight, based on the weight of the total CS composition.

[1129] xi) Dustable powder (DP, DS)

[1130] 1 - 10% by weight of at least one compound of formula (I) is finely ground and intimately mixed with the corresponding amount of a solid carrier (such as finely divided kaolin) to give a total of 100% by weight.

[1131] xii) Granule (GR, FG)

[1132] 0.5 - 30% by weight of at least one compound of formula (I) is finely ground and combined with the corresponding amount of a solid carrier (such as silicate) to give a total of 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed.

[1133] xiii) Ultra-low volume liquid agent (UL)

[1134] Dissolve 1-50% by weight of at least one compound of formula (I) in a corresponding amount of an organic solvent (such as aromatic hydrocarbons) to obtain a total amount of 100% by weight.

[1135] The composition types i) to xiii) may optionally contain other auxiliaries, such as 0.1-1% by weight of a preservative, 0.1-1% by weight of an antifoaming agent, 0.1-1% by weight of a dye and / or pigment, and 5-10% by weight of an antifreeze.

[1136] Mixture / composition

[1137] The compound of formula (I) and the composition of the present invention can be mixed with other active ingredients, such as fungicides, bactericides, acaricides, nematicides, insecticides, biocontrol agents or herbicides. Mixtures with fertilizers, growth regulators, safeners, nitrification inhibitors, semiochemicals and / or other agriculturally beneficial formulations are also possible. This can broaden the activity spectrum or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in the Pesticide Manual, 17th edition.

[1138] Examples of fungicides that can be mixed with the compound of formula (I) and the composition of the present invention are:

[1139] 1) Inhibitors of ergosterol biosynthesis, such as (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) 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, (1.027) (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-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.(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)oxiranyl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl]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, (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, (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) mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-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)oxirane-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)oxirane-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (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)oxiranyl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylthio)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylthio)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl]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-methylformimidamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-methylformimidamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]thio}phenyl)-N-ethyl-N-methylformimidamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-methylformimidamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-methylformimidamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-methylformimidamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)thio]phenoxy}phenyl)-N-ethyl-N-methylformimidamide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-methylformimidamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformimidamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]thio}-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, (1.073) N'-(4-{3-[(difluoromethyl)thio]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, (1.N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylformimidamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformimidamide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformimidamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformimidamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformimidamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformimidamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformimidamide and (1.081) ipfentrifluconazole, (1.082) 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, (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]benzonitrile, (1.087) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylformimidamide, (1.088) N'-{5-bromo-2-methyl-6-[(1-propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylformimidamide, (1.089) hexaconazole, (1.090) penconazole, (1.091) fenbuconazole, (1.092) Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate.

[1140] 2) Inhibitors of respiratory chain 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) isopyrazam (trans - epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (trans - epimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (trans - epimeric racemate 1RS,4SR,9SR), (2.013) isopyrazam (mixture of cis - epimeric racemate 1RS,4SR,9RS and trans - epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (cis - epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam (cis - epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (cis - epimeric racemate 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 - indene - 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 - indene - 4 - yl) benzamide, (2.027) 3 - (difluoromethyl) - 1 - methyl - N - (1,1,3 - trimethyl - 2,3 - dihydro - 1H - indene - 4 - yl) - 1H - pyrazole - 4 - carboxamide, (2.(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) isoflucypram, (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-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-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-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, (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, (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) pyrapropoyne, (2.058) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059) N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide and (2.060) cyclobutrifluram.

[1141] 3) Inhibitors of respiratory chain 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) famoxadone, (3.010) fenamidone, (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, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]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.Methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) metyltetraprole, (3.031) florylpicoxamid, (3.032) N-{[4-methoxy-3-(propanoyloxy)-2-pyridinyl]carbonyl}-L-alanine (2S,3S)-3-(o-tolyl)butan-2-yl ester.

[1142] 4) Inhibitors of mitosis and cell division, such as (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) pyridachlometyl, (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-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-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-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.026) fluopimomide.

[1143] 5) Compounds capable of having multi-site action, 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, (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) metiram zinc, (5.017) oxine-copper, (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.

[1144] 6) Compounds that can induce host defense, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

[1145] 7) Inhibitors of amino acid and / or protein biosynthesis, such as (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.

[1146] 8) Inhibitors of ATP production, such as (8.001) silthiofam.

[1147] 9) Inhibitors of cell wall synthesis, such as (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.

[1148] 10) Inhibitors of lipid and membrane synthesis, such as (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[1149] 11) Inhibitors of melanin biosynthesis, such as (11.001) tricyclazole, (11.002) tolprocarb.

[1150] 12) Inhibitors of nucleic acid synthesis, such as (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[1151] 13) Inhibitors of signal transduction, such as (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.

[1152] 14) Compounds capable of acting as uncoupling agents, such as (14.001) fluazinam, (14.002) meptyldinocap.

[1153] 15) Other fungicides, such as (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) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl 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) phosphorous 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) 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]ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-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)-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}phenyl methanesulfonate, (15.045) 2-phenylphenol and salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) 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]butanoic 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) {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}but-3-yn-1-yl carbamate, (15.056) (2Z)-ethyl 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) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (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-methylformimidamide, (15.065) N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylformimidamide, (15.066) 2-{2-[(7,8-difluoro-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-benzimidazol-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, (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-methyl-carbodiimido]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.084) N-[(Z)-N-Methoxy-C-methyl-carbodiimido]-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]propanamide, (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-trifluoro-propanamide, (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]propanamide, (15.093) N-Methoxy-N-[[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) 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) ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylate, (15.109) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.111) N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.113) 1-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114) 1-(6-(difluoromethyl)-5-methylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115) 1-(5-(fluoromethyl)-6-methylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116) 1-(6-(difluoromethyl)-5-methoxypyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.117) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl dimethylcarbamate, (15.118) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propanamide, (15.119) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxazol-6-yl methanesulfonate, (15.120) 9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxazol-6-yl methanesulfonate, (15.121) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxazol-6-yl methanesulfonate, (15.122) 3-[2-(1-{[3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxin-6-yl mesylate, (15.123) 1-(6,7-Dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.124) 8-Fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide, (15.125) 8-Fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15.126) N-(2,4-Dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide, (15.127) N-[(2S)-2,4-Dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide and (15.128) D-tagatose.

[1154] All named mixed components of classes (1) to (15) described above may exist in the form of the free compound or, if their functional groups are capable of forming salts, in the form of their agriculturally acceptable active salts.

[1155] The compounds of formula (I) and the compositions of the present invention may also be combined with one or more biocontrol agents.

[1156] As used herein, the term "biocontrol" is defined as the control of pests, such as phytopathogenic fungi and / or insects and / or mites and / or nematodes, by the use or utilization of biocontrol agents.

[1157] As used herein, the term "biocontrol agent" is defined as organisms that are not pests and / or proteins or secondary metabolites produced by such organisms for the purpose of biocontrol. Mutants of the second organism should be included within the definition of biocontrol agents. The term "mutant" refers to variants of the parent strain, as well as the methods for obtaining mutants or variants, in which the pesticidal activity is greater than the pesticidal activity expressed by the parent strain. The "parent strain" herein is defined as the original strain before mutagenesis. In order to obtain such mutants, the parent strain can be treated with chemicals such as N-methyl-N'-nitro-N-nitrosoguanidine, ethyl methylsulfone, or irradiated with gamma rays, x-rays or ultraviolet light, or by other methods well known to those skilled in the art. Known biocontrol agent mechanisms include controlling root rot by competing for fungal space on the root surface by gut bacteria. Bacterial toxins (such as antibiotics) have been used to control pathogens. The toxins can be isolated and applied directly to plants, or bacterial species can be applied to produce the toxin in situ.

[1158] "Variant" means a strain having all the identifying characteristics of the NRRL or ATCC accession number shown herein and can be identified as having a genome that hybridizes with the genome of the NRRL or ATCC accession number under high stringency conditions.

[1159] "Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex stabilized by hydrogen bonds between nucleotide residues. The hydrogen bonds can occur through Watson-Crick base pairing, Hoogstein binding, or any other specific sequence means. The complex can contain two strands that form a double-stranded structure, three or more strands that form a multi-stranded complex, a single self-hybridizing strand, or any combination of these. The hybridization reaction can be carried out under different "stringency" conditions. Generally, low stringency hybridization reactions are carried out in a solution of 10X SSC or equivalent ionic strength / temperature at about 40 °C. Normal stringency hybridizations are usually carried out in 6X SSC at about 50 °C, while high stringency hybridization reactions are usually carried out in 1X SSC at about 60 °C.

[1160] A variant of the specified NRRL or ATCC accession number can also be defined as a strain having a genomic sequence with greater than 85%, more preferably greater than 90%, or more preferably greater than 95% sequence identity compared to the genome of the specified NRRL or ATCC accession number. A polynucleotide or polynucleotide region (or a polypeptide or polypeptide region) has a certain percentage (e.g., 80%, 85%, 90%, or 95%) of "sequence identity" with another sequence means that when aligned, the two sequences being compared have the same percentage of bases (or amino acids). Such alignments and the percentage of homology or sequence identity can be determined using software programs known in the art, for example, those described in Current Protocols in Molecular Biology (F.M. Ausubel et al., eds., 1987).

[1161] NRRL is the abbreviation of Agricultural Research Service Culture Collection, which is an international depository institution established for the purpose of depositing microbial strains under the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure. Its address is National Center for Agricultural Utilization Research, Agricultural Research service, U.S. Department of Agriculture, 1815 North university Street, Peroira, Illinois 61604 USA.

[1162] ATCC is the abbreviation of American Type Culture Collection. According to the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure, this institution is an international depository established for the purpose of depositing microbial strains. Its address is ATCC Patent Depository, 10801 University Blvd., Manassas, VA 10110 USA.

[1163] Examples of biocontrol agents that can be combined with the compounds of formula (I) and the compositions of the present invention are:

[1164] (A) Antibacterial agents selected from:

[1165] (A1) Bacteria, such as (A1.1) Bacillus subtilis, especially strain QST713 / AQ713 (available from Bayer CropScience LP, US under the name SERENADE OPTI or SERENADE ASO, NRRL accession number B21661, US Patent No. 6,060,051); (A1.2) Bacillus sp., especially strain D747 (available from Kumiai Chemical Industry Co., Ltd. under the name DOUBLE obtained), accession number FERM BP-8234, US Patent No. 7,094,592; (A1.3) Bacillus pumilus, especially strain BU F-33, NRRL accession number 50185 (available from BASF as part of the product, EPA registration number 71840-19); (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24, accession number DSM 10271 (available from Novozymes under the name or ECO (EPA registration number 70127-5) obtained); (A1.5) Paenibacillus sp. strains, accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297; (A1.6) Bacillus subtilis strain BU1814, (available from BASF SE under the name PLUS, FLEX and (A1.7) Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (WO 2013 / 034938) from Certis USA LLC, a subsidiary of Mitsui & Co.; (A1.8) Bacillus subtilis CX-9060 from Certis USA LLC, a subsidiary of Mitsui & Co.; (A1.9) Paenibacillus polymyxa, especially strain AC-1 (e.g., from Green Biotech Company Ltd.) ); (A1.10) Pseudomonas proradix (e.g., from Sourcon Padena) ); (A1.11) Pantoea agglomerans, especially strain E325 (accession number NRRL B-21856) (available from Northwest Agri Products as BLOOMTIME BIOLOGICAL TM FD BIOPESTICIDE); and

[1166] (A2) Fungi, such as (A2.1) Aureobasidium pullulans, especially blastospores of strain DSM14940, blastospores of strain DSM14941, or a mixture of blastospores of strains DSM14940 and DSM14941 (e.g., from bio-ferm, CH and BLOSSOM ); (A2.2) Pseudozyma aphidis (as disclosed in WO2011 / 151819 by Yissum Research Development Company of the Hebrew University of Jerusalem); (A2.3) Saccharomyces cerevisiae, especially strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938, or CNCM No. I-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790);

[1167] (B) A biocidal fungicide selected from the following:

[1168] (B1) Bacteria, such as (B1.1) Bacillus subtilis, in particular strain QST713 / AQ713 (available from Bayer CropScience LP, US under the name SERENADE OPTI or SERENADE ASO, NRRL accession number B21661 and described in US Patent No. 6,060,051); (B1.2) Bacillus pumilus, in particular strain QST2808 (available from Bayer CropScience LP, US under such name, NRRL accession number B-30087 and described in US Patent No. 6,245,551); (B1.3) Bacillus pumilus, in particular strain GB34 (available from Bayer AG, DE under the name Yield such name); (B1.4) Bacillus pumilus, in particular strain BU F-33, NRRL accession number 50185 (available as part of the CARTISSA product from BASF, EPA registration number 71840-19); (B1.5) Bacillus amyloliquefaciens, in particular strain D747 (available from Kumiai Chemical Industry Co., Ltd. under the name Double Nickel TM such name, accession number FERM BP-8234, US Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan under the name WP, registered as a biopesticide in Taiwan, China under the accession numbers 4764, 5454, 5096 and 5277); (B1.7) Bacillus subtilis strain MBI 600 (available from BASF SE under the name SUBTILEX), accession number NRRL B-50595, US Patent No. 5,061,495; (B1.8) Bacillus subtilis strain GB03 (available from Bayer AG, DE under the name such name); (B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24, accession number DSM 10271 (available from Novozymes under the name or ECO (EPA registration number 70127-5)); (B1.10) Bacillus mycoides, isolate J, accession number B-30890 (available from Certis USA LLC (a subsidiary of Mitsui & Co.) under the name BMJ or WG and LifeGard TM(obtained); (B1.11) Bacillus licheniformis, especially strain SB3086, accession number ATCC 55406, WO 2003 / 000051 (available from Novozymes as Biocontrol fungicide and GREEN RELEAF TM (obtained); (B1.12) Paenibacillus sp. strain, accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297; (B1.13) Bacillus subtilis strain BU1814, (available from BASF SE as PLUS, FLEX and EXTR obtained); (B1.14) Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co.); (B1.15) Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768; WO 2014 / 028521) (from Marrone Bio Innovations ); (B1.16) Bacillus amyloliquefaciens strain FZB42, accession number DSM 23117 (available from ABiTEP, DE as obtained); (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC Corporation (WG) and (WP)); (B1.18) Paenibacillus mojavensis strain R3B from Certis USA LLC (a subsidiary of Mitsui & Co.) (accession number NCAIM(P)B001389) (WO 2013 / 034938); (B1.19) Paenibacillus polymyxa subsp. plantarum from BASF SE (WO 2016 / 020371); (B1.20) Paenibacillus epiphyticus from BASF SE (WO2016 / 020371); (B.1.21) Pseudomonas chlororaphis strain AFS009, accession number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER from AgBiome Innovations, US TM and ); (B1.22) Pseudomonas chlororaphis, in particular strain MA342 (e.g., supplied by Bioagri and Koppert and ); (B1.23) Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (from Novozymes and ); (B1.24) Agrobacterium radiobacter strain K84 (e.g., from AgBioChem, CA ); (B1.25) Agrobacterium radiobacter strain K1026 (e.g., NOGALL from BASF SE TM ); (B1.26) Bacillus subtilis KTSB strain (from Donaghys ); (B1.27) Bacillus subtilis IAB / BS03 (AVIV from STK Bio-AgTechnologies TM ); (B1.28) Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan as WP, registered as a biopesticide in Taiwan, China under registration numbers 4764, 5454, 5096 and 5277); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN from the University of Pretoria TM ); (B1.30) Bacillus methylotrophicus strain BAC-9912 (from the Chinese Academy of Sciences’ Institute of Applied Ecology); (B1.31) Pseudomonas proradix (e.g., from Sourcon Padena ); (B1.32) Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (registration number DSM 7206) (from Verdera from BioWorks see Crop Protection 2006, 25, 468-475); (B1.33) Pseudomonas fluorescens strain A506 (e.g., supplied by NuFarm ); and

[1169] (B2) Fungi, such as: (B2.1) Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM-9660; for example from Bayer CropScience Biologics GmbH ); (B2.2) Metschnikowia fructicola, especially strain NRRL Y-30752; (B2.3) Microsphaeropsis ochracea; (B2.5) Trichoderma atroviride, especially strain SC1 (registration number CBS 122089, WO 2009 / 116106 and US Patent No. 8,431,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g., Sentinel from Agrimm Technologies Limited); (B2.6) Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa Simb-T5 (from Simbiose Agro); (B2.14) Gliocladium roseum (also known as Clonostachys rosea f. rosea), especially strain 321U from Adjuvants Plus, strain ACM941 disclosed in Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3):519-524), or strain IK726 (Jensen DF et al Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain ‘IK726’; Australas Plant Pathol. 2007;36:95–101); (B2.35) Talaromyces flavus, strain V117b; (B2.36) Trichoderma viride, especially strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161:125-137); (B2.37) Trichoderma asperellum, especially strain SKT-1, accession number FERM P-16510 (e.g., from Kumiai Chemical Industry Co., Ltd.). ), strain T34 (e.g., T34 Biocontrol provided by Biocontrol Technologies S.L., ES) or strain ICC 012 from Isagro; (B2.38) Trichoderma atroviride, strain CNCM I-1237 (e.g., WP from Agrauxine, FR). ; (B2.39) Trichoderma atroviride, strain number V08 / 002387; (B2.40) Trichoderma atroviride, strain NMI number V08 / 002388; (B2.41) Trichoderma atroviride, strain NMI number V08 / 002389; (B2.42) Trichoderma atroviride, strain NMI number V08 / 002390; (B2.43) Trichoderma atroviride, strain LC52 (e.g., Tenet provided by Agrimm Technologies Limited); (B2.44) Trichoderma atroviride, strain ATCC 20476 (IMI206040); (B2.45) Trichoderma atroviride, strain T11 (IMI352941 / CECT20498); (B2.46); Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g., from Makhteshim, US). ); (B2.49) Trichoderma asperellum, especially strain kd (e.g., T-Gro from Andermatt Biocontrol); (B2.50) Trichoderma harzianum, strain ITEM 908 (e.g., Trianum-P from Koppert); (B2.51) Trichoderma harzianum, strain TH35 (e.g., Root-Pro provided by Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens), especially strain GL-21 (e.g., SoilGard provided by Certis, US); (B2.53) Trichoderma viride, strain TV1 (e.g., Trianum-P provided by Koppert); (B2.54) Ampelomyces quisqualis, especially strain AQ 10 (e.g., AQ provided by IntrachemBio Italia). ); (B2.56) Blastospores of Aureobasidium pullulans, especially strain DSM14940; (B2.57) Blastospores of Aureobasidium pullulans, especially strain DSM 14941; (B2.58) A mixture of blastospores of Aureobasidium pullulans, especially strains DSM14940 and DSM 14941 (e.g., provided by bio-ferm, CH) ); (B2.64) Cladosporium cladosporioides, strain H39, accession number CBS122244, US 2010 / 0291039 (provided by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonostachys roseaf.catenulate) strain J1446 (e.g., provided by Lallemand) ); (B2.70) Conidia of Lecanicillium lecanii (formerly known as Verticillium lecanii) strain KV01 (e.g., provided by Koppert / Arysta) ); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183; (B2.75) Trichoderma atroviride, strain SKT-1 (FERM P-16510), Japanese Patent Publication (Kokai) No. 11-253151 A; (B2.76) Trichoderma atroviride, strain SKT-2 (FERM P-16511), Japanese Patent Publication (Kokai) No. 11-253151A; (B2.77) Trichoderma atroviride, strain SKT-3 (FERM P-17021), Japanese Patent Publication (Kokai) No. 11-253151A; (B2.78) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMICC 392151 CABI, e.g., BioDerma provided by AGROBIOSOL DE MEXICO, S.A. DE C.V.); (B2.79) Trichoderma harzianum, strain DB 103 (obtainable as T-Gro 7456 from Dagutat Biolab); (B2.80) Trichoderma polysporum, strain IMI 206039 (e.g., Binab TF WP provided by BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum, accession number Ts3550 (e.g., Tricovab provided by CEPLAC, Brazil); (B2.83) Ulocladium oudemansii strain U3, accession number NM 99 / 06216 (e.g., and from BioWorks, Inc. ); (B2.84) Verticillium albo-atrum (formerly V. dahliae), strain WCS850 with accession number WCS850, deposited at Central Bureau for Fungi Cultures (e.g., DUTCH provided by Tree Care Innovations ); (B2.86) Verticillium chlamydosporium; (B2.87) a mixture of Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012) (accession number CABI CC IMI 392716) and Trichoderma gamsii strain (formerly T. viride) strain ICC080 (accession number IMI 392151) (e.g., BIO-TAM from Isagro USA, Inc. TM and provided by Agrobiosol de Mexico, S.A.de C.V. ); (B2.88) Trichoderma asperelloides JM41R (accession number NRRL B-50759) (TRICHO from BASF SE ); (B2.89) Aspergillus flavus strain NRRL 21882 (product known as from Syngenta / ChemChina); (B2.90) Chaetomium cupreum (accession number CABI 353812) (e.g., BIOKUPRUM provided by AgriLife TM ); (B2.91) Saccharomyces cerevisiae, especially strain LASO2 (from Agro-Levures et Dérivés), strain LAS117 cell wall (from Lesaffre from BASF SE ), strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938, CNCM No. I-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790); (B2.92) Trichoderma virens strain G-41, formerly also known as Gliocladium virens (accession number ATCC 20906) (e.g., PLUS WP and PLUS WP) from BioWorks, US; (B2.93) Trichoderma hamatum, accession number ATCC28012; (B2.94) Ampelomyces quisqualis strain AQ10, accession number CNCM I-807 (e.g., AQ ) provided by IntrachemBio Italia; (B2.95) Phlebiopsis gigantea strain VRA 1992 (from Danstar Ferment (C); (B2.96) Penicillium steckii from BASF SE (DSM 27859; WO2015 / 067800); (B2.97) Chaetomium globosum (available from Rivale obtained); (B2.98) Cryptococcus flavescens, strain 3C (NRRL Y-50378); (B2.99) Dactylaria candida; (B2.100) Dilophosphora alopecuri (can be obtained from TWIST ); (B2.101) Fusarium oxysporum, strain Fo47 (available from NaturalPlant Protection ); (B2.102) Pseudozyma flocculosa, strain PF-A22 UL (available from Plant Products Co., CA L); (B2.103) Trichoderma gamsii (formerly T. viride), strain ICC 080 (IMI CC 392151CABI) (available from AGROBIOSOL DEMEXICO, S.A.DE C.V. ); (B2.104) Trichoderma fertile (e.g., the product TrichoPlus from BASF); (B2.105) Muscodor roseus, especially strain A3-5 (accession number NRRL30548); (B2.106) Simplicillium lanosoniveum;

[1170] Biological control agents having the effect of improving plant growth and / or plant health, which can be combined with the compounds of the present invention, including:

[1171] (C1) Bacteria selected from: Bacillus pumilus, especially strain QST2808 (accession number NRRL No. B-30087); Bacillus subtilis, especially strain QST713 / AQ713 (NRRL accession number B-21661 and described in U.S. Patent No. 6,060,051; available from Bayer CropScience LP, US in OPTI or obtained by ASO; Bacillus subtilis, especially strain AQ30002 (accession number NRRL B-50421 and described in US Patent Application No. 13 / 330,576); Bacillus subtilis, especially strain AQ30004 (NRRL B-50455 and described in US Patent Application No. 13 / 330,576); Sinorhizobium meliloti strain NRG-185-1 (from Bayer CropScience's GOLD); Bacillus subtilis strain BU1814, (available from BASF SE as obtained); Bacillus subtilis rm303 (from Biofilm CropProtection's ); Bacillus amyloliquefaciens pm414 (from Biofilm Crop Protection's ); Bacillus mycoides BT155 (NRRL No. B-50921), Bacillus mycoides EE118 (NRRL No. B-50918), Bacillus mycoides EE141 (NRRL No. B-50916), Bacillus mycoides BT46-3 (NRRL No. B-50922), a member of the Bacillus cereus family EE128 (NRRL No. B-50917), Bacillus thuringiensis BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7), a member of the Bacillus cereus family EE349 (NRRL No. B-50928), Bacillus amyloliquefaciens SB3281 (ATCC#PTA-7542; WO2017 / 205258), Bacillus amyloliquefaciens TJ1000 (available from Novozymes as obtained); Bacillus firmus, especially strain CNMC I-1582 (e.g., from BASF SE's ); Bacillus pumilus, especially strain GB34 (e.g., from Bayer Crop Science, DE's YIELD ); Bacillus amyloliquefaciens, especially strain IN937a; Bacillus amyloliquefaciens, especially strain FZB42 (e.g., from ABiTEP, DE's ); Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015); a mixture of Bacillus muscicola FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as (WG), (WP) obtained); Bacillus cereus, especially strain BP01 (ATCC 55675; e.g., from Arysta Lifescience, US ); Bacillus subtilis, especially strain MBI 600 (e.g., from BASF SE ); Bradyrhizobium japonicum (e.g., from Novozymes ); Mesorhizobium cicer (e.g., NODULATOR from BASF SE); Rhizobium leguminosarium biovar viciae (e.g., NODULATOR from BASF SE); Delftia acidovorans, especially strain RAY209 (e.g., from BrettYoung Seeds ); Lactobacillus sp. (e.g., from LactoPAFI ); Paenibacillus polymyxa, especially strain AC-1 (e.g., from Green Biotech Company Ltd. ); Pseudomonas proradix (e.g., from Sourcon Padena ); Azospirillum brasilense (e.g., from KALO, Inc. ); Azospirillum lipoferum (e.g., VERTEX-IF from TerraMax, Inc. TM ); a mixture of Azotobacter vinelandii and Clostridium pasteurianum (available from Agrinos as obtained); Pseudomonas aeruginosa, especially strain PN1; Rhizobium leguminosarum, especially bv. viceae strain Z25 (accession number CECT 4585); Azorhizobium caulinodans, especially strain ZB-SK-5; Azotobacter chroococcum, especially strain H23; Azotobacter vinelandii, especially strain ATCC 12837; Bacillus siamensis, especially strain KCTC 13613T; Bacillus tequilensis, especially strain NII-0943; Serratia marcescens, especially strain SRM (accession number MTCC 8708); Thiobacillus sp. (e.g., from Cropaid Ltd UK ); and

[1172] (C2) Fungi selected from the following: Purpureocillium lilacinum (formerly Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550; e.g., BioAct from Bayer CropScience Biologics GmbH), Penicillium bilaii, strain ATCC 22348 (e.g., ) from Acceleron BioAg, Scopulariopsis flava strain V117b; Trichoderma atroviride strain CNCM I-1237 (e.g., WP), Trichoderma viride, such as strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161:125 - 137); Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132; e.g., Sentinel from Agrimm Technologies Limited); Trichoderma atroviride strain SC1 described in International Application No. PCT / IT2008 / 000196; Trichoderma asperellum strain kd (e.g., T - Gro from Andermatt Biocontrol); Trichoderma asperellum strain Eco - T (Plant Health Products, ZA); Trichoderma harzianum strain T - 22 (e.g., Trianum - P from Andermatt Biocontrol or Koppert); Myrothecium verrucaria strain AARC - 0255 (e.g., DiTera from Valent Biosciences TM ); Penicillium strain ATCCATCC20851; Pythium oligandrum strain M1 (ATCC 38472; e.g., Polyversum from Bioprepraty, CZ); Trichoderma viride strain GL - 21 (e.g., ) from Certis, USA; Verticillium albo - atrum (formerly V. dahliae) strain WCS850 (CBS 276.92; e.g., DutchTrig from Tree Care Innovations); Trichoderma atroviride, especially strain number V08 / 002387, strain number NMI number V08 / 002388, strain number NMI number V08 / 002389, strain number NMI number V08 / 002390; Trichoderma harzianum strain ITEM 908; Trichoderma harzianum, strain TSTh20; Trichoderma harzianum strain 1295 - 22; Pythium oligandrum strain DV74; Rhizopogon amylopogon (e.g., included in Myco - Sol from Helena Chemical Company); Rhizopogon fulvigleba (e.g., included in Myco - Sol from Helena Chemical Company); and Trichoderma viride strain GI - 3;

[1173] Insecticidal active biocontrol agents, selected from:

[1174] (D1) Bacteria selected from the following: Bacillus thuringiensis subsp. aizawai, especially strain ABTS-1857 (SD-1372; e.g., ) from Valent BioSciences); Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC, a subsidiary of Mitsui & Co.); Bacillus sphaericus, especially serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., ) from Valent BioSciences, US); Bacillus thuringiensis subsp. kurstaki strain BMP 123 from Becker Microbial Products, IL; Bacillus thuringiensis subsp. aizawai, especially serotype H-7 (e.g., WG) from Valent BioSciences, US); Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g., ES) from Valent BioSciences, US); Bacillus thuringiensis subsp. kurstaki strain BMP 123 provided by Becker Microbial Products, IL; Bacillus thuringiensis israelensis strain BMP 144 (e.g., ) provided by Becker Microbial Products IL; Burkholderia spp., especially Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (accession number NRRL B-50319; WO 2011 / 106491 and WO 2013 / 032693; e.g., MBI-206TGAI and ) from Marrone Bio Innovations; Chromobacterium subtsugae, especially strain PRAA4-1T (MBI-203; e.g., ); Milky white pathogenic bacteria (Paenibacillus popilliae) (previously Bacillus popilliae; e.g., MILKY SPORE POWDER from St. Gabriel Laboratories TM and MILKY SPORE GRANULAR TM ); Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., provided by Valent BioSciences, US ); Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., from AEF Global ); Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428; e.g., FC from BioFa DE ); Bacillus thuringiensis var. japonensis strain Buibui; Bacillus thuringiensis subsp. kurstaki strain ABTS 351; Bacillus thuringiensis subsp. kurstaki strain PB 54; Bacillus thuringiensis subsp. kurstaki strain SA 11; Bacillus thuringiensis subsp. kurstaki strain SA 12; Bacillus thuringiensis subsp. kurstaki strain EG 2348; Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC provided by Changzhou Jianghai Chemical Factory); Bacillus thuringiensis subsp. aizawai strain GC-91; Serratia entomophila (e.g., provided by Wrightson Seeds ); Serratia marcescens, especially strain SRM (accession number MTCC 8708); and Wolbachia pipientis ZAP strain (e.g., ZAP from MosquitoMate ); and

[1175] (D2)Fungi selected from the following: Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain apopka 97; Beauveria bassiana strain ATCC 74040 (e.g., from Intrachem Bio Italia ); Beauveria bassiana strain GHA (accession number ATCC 74250; e.g., from Laverlam International Corporation ES and ); Zoophtora radicans; Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073), Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075), and Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074) (WO 2017 / 066094; Pioneer Hi-Bred International); Beauveria bassiana strain ATP02 (accession number DSM 24665). Among these, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain apopka 97 is particularly preferred;

[1176] (E)Viruses selected from the following: Adoxophyes orana (summerfruit tortrix) granulovirus (GV), Cydia pomonella (codling moth) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nucleopolyhedrovirus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, and Spodoptera littoralis (African cotton leafworm) NPV;

[1177] (F) Bacteria and fungi that can be added as an "inoculant" to a plant or plant part or plant organ and promote plant growth and plant health by virtue of their specific properties. Examples of such bacteria and fungi are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., especially 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., especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp. and Streptomyces spp.; and

[1178] (G) Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that can be used as biocontrol agents are: for example, garlic (Allium sativum), wormwood (Artemisia absinthium), azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), pyrethrum / pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem TM insecticide", rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extracts (especially rapeseed powder or mustard powder), and bio-insecticidal / acaricidal active substances obtained from olive oil, especially unsaturated fats / carboxylic acids with a carbon chain length of C 16 -C 20 as the active ingredient, for example, as contained in a product with the trade name .

[1179] The compounds of formula (I) and the compositions of the present invention can be combined with one or more active ingredients selected from insecticides, acaricides, and nematicides.

[1180] "Insecticides" and the term "insecticidal" refer to a substance that can increase the mortality rate of insects or inhibit their growth rate. As used herein, the term "insects" includes all organisms in the class "Insecta".

[1181] "Nematicide" and "nematicidal" mean a substance that can increase the mortality rate of nematodes or inhibit their growth rate. Generally, the term "nematode" includes the eggs, larvae, juveniles, and mature forms of said organisms.

[1182] "Acaricide" and "acaricidal" mean a substance that can increase the mortality rate of ectoparasites belonging to the subclass Acari of the class Arachnida or inhibit their growth rate.

[1183] Examples of insecticides, acaricides, and nematicides that can be mixed with the compounds of formula (I) and the compositions of the present invention are:

[1184] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, such as alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, 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, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

[1185] (2) GABA-gated chloride channel blockers, such as cyclodiene-organochlorines, such as chlordane and endosulfan, or phenylpyrazoles (fiproles), such as ethiprole and fipronil.

[1186] (3) Sodium channel modulators, such as pyrethroids, for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, and transfluthrin, or DDT, or methoxychlor.

[1187] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone.

[1188] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosyns, such as spinetoram and spinosad.

[1189] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin, and milbemectin.

[1190] (7) Juvenile hormone mimics, such as juvenile hormone analogs, such as hydroprene, kinoprene, and methoprene, or fenoxycarb, or pyriproxyfen.

[1191] (8) Various non-specific (multisite) inhibitors, such as alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate generators, such as diazomet and metam.

[1192] (9) Chordotonal Organ modulators, such as pymetrozine or flonicamid.

[1193] (10)Mite growth inhibitors, such as clofentezine, hexythiazox, diflovidazin, or etoxazole.

[1194] (11)Insect gut membrane microbial disruptors, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and the following B.t. plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1.

[1195] (12)Mitochondrial ATP synthase inhibitors, such as ATP disruptors, such as diafenthiuron; or organotin compounds, such as azocyclotin, cyhexatin, and fenbutatinoxide; or propargite, or tetradifon.

[1196] (13)Uncoupling agents that interrupt oxidative phosphorylation by disrupting the proton gradient, such as chlorfenapyr, DNOC, and sulfluramid.

[1197] (14)Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium.

[1198] (15)Type 0 chitin biosynthesis inhibitors, such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[1199] (16)Type 1 chitin biosynthesis inhibitors, such as buprofezin.

[1200] (17)Ecdysis disruptors (especially for Diptera, i.e., two-winged insects), such as cyromazine.

[1201] (18)Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

[1202] (19)Octopamine receptor agonists, such as amitraz.

[1203] (20)Mitochondrial complex III electron transport inhibitors, such as hydramethylnone, acequinocyl, or fluacrypyrim.

[1204] (21)Mitochondrial complex I electron transport inhibitors, such as METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, and tolfenpyrad, or rotenone (Derris).

[1205] (22)Voltage-dependent sodium channel blockers, such as indoxacarb and metaflumizone.

[1206] (23) Acetyl-CoA carboxylase inhibitors, such as tetronic acid and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[1207] (24) Mitochondrial complex IV electron transport inhibitors, such as phosphines, such as aluminium phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides, such as calcium cyanide, potassium cyanide and sodium cyanide.

[1208] (25) Mitochondrial complex II electron transport inhibitors, such as β-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen, and carboxanilides, such as pyflubumide.

[1209] (28) Ryanodine receptor modulators, such as diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide.

[1210] Other active compounds, such as afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, chloroprallethrin, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon-momfluthrin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, kappa-bifenthrin, kappa-tefluthrin, lotilaner, meperfluthrin, paichongding, pyridalyl, pyrifluquinazon, pyriminostrobin, spirobudiclofen, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tigolaner, tioxazafen, thiofluoximate, triflumezopyrim and methyl iodideiodomethane); there are also preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), 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), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 106457) (CAS 637360-23-7), 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 WO 2010052161) (CAS 1225292-17-0), ethyl 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carbonate (known from EP2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160) (CAS 792914-58-0), PF1364 (known from JP2010 / 018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO2012 / 029672) (CAS 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridinyl)methyl]-2-pyridinylidene]-1,1,1-trifluoro-propan-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-pyridinyl)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-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide, and (-)-N-[3-chloro-1-(3-pyridinyl)-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-pyridinyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-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-pyridinyl)-1H-pyrazole-5-carboxamide (known from WO2011 / 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); 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylate (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-mannopyranose (known from US2014 / 0275503 A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-azabicyclo[3.2.1]octane (known from WO 2007040280 A1, WO2007040282 A1) (CAS934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide (known from WO 2015 / 058021 A1, WO 2015 / 058028 A1) (CAS 1477919-27-9) and N-[4-(aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from WO 2013 / 115391 A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010 / 066780 A1, WO 2011 / 151146 A1) (CAS 1229023-34-0), 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-yl ethyl carbonate (known from WO 2010 / 066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide (known from DE 3639877 A1, WO 2012029672 A1) (CAS1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide (known from WO 2016005276 A1) (CAS 1689566-03-7), [N(Z)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide (CAS 1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from WO 2011 / 105506 A1, WO 2016 / 133011A1 is informed (CAS 1332838-17-1).

[1211] Examples of herbicides that can be mixed with the compounds of formula (I) and the compositions of the present invention are:

[1212] acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bixlozone, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassiumbromoxynil - heptanoate, bromoxynil - octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone - ethyl, chloramben, chlorbromuron, 1 - {2 - chloro - 3 - [(3 - cyclopropyl - 5 - hydroxy - 1 - methyl - 1H - pyrazol - 4 - yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin - 2 - one, 4 - {2 - chloro - 3 - [(3,5 - dimethyl - 1H - pyrazol - 1 - yl)methyl]-4-(methylsulfonyl)benzoyl}-1,3 - dimethyl - 1H - pyrazol - 5 - yl 1,3 - dimethyl - 1H - pyrazole - 4 - carboxylate, chlorfenac, chlorfenac - sodium, chlorfenprop, chlorflurenol, chlorflurenol - methyl, chloridazon, chlorimuron, chlorimuron - ethyl, 2 - [2 - chloro - 4-(methylsulfonyl)-3-(morpholin - 4 - ylmethyl)benzoyl]-3 - hydroxycyclohex - 2 - en - 1 - one, 4 - {2 - chloro - 4-(methylsulfonyl)-3 - [(2,2,2 - trifluoroethoxy)methyl]benzoyl}-1 - ethyl - 1H - pyrazol - 5 - yl 1,3 - dimethyl - 1H - pyrazole - 4 - carboxylate, chlorophthalim, chlorotoluron, chlorthal - dimethyl, 3 - [5 - chloro - 4-(trifluoromethyl)pyridin - 2 - yl]-4 - hydroxy - 1 - methylimidazolidin - 2 - one, chlorsulfuron, cinidon, cinidon - ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafopclodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium, 2,4-D-diolamin, 2,4-D-ethyl ester, 2,4-D-2-ethylhexyl ester, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester, 2,4-D-isopropylammonium salt, 2,4-D-potassium salt, 2,4-D-triisopropanolammonium salt and 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium salt, 2,4-DB-isooctyl ester, 2,4-DB-potassium salt and 2,4-DB-sodium salt, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2,4-dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametrynDimethenamid, dimethenamid-P, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 1,3-dimethyl-4-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-yl 1,3-dimethyl-1H-pyrazole-4-carboxylate, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, 2,2-dimethylolpropionic acid (DMPA), dinitro-o-cresol (DNOC), endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, ethyl [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, F-9960, F-5231 (i.e., N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methylFlazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium, and flurenol-methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium,Glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, and glyphosate-trimesium, H-9201 (i.e., O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropyl phosphorothioate), Halauxifen, Halauxifen-methyl, Halosafen, Halosulfuron, Halosulfuron-methyl, Haloxyfop, Haloxyfop-P, Haloxyfop-ethoxyethyl, Haloxyfop-P-ethoxyethyl, Haloxyfop-methyl, Haloxyfop-P-methyl, Hexazinone, HW-02 (i.e., 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)methanone, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione, Imazamethabenz, Imazamethabenz-methyl, Imazamox, Imazamox-ammonium, Imazapic, Imazapic-ammonium, Imazapyr, Imazapyr-isopropylammonium, Imazaquin, Imazaquin-ammonium,Imazethapyr, imazethapyr - immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron - methyl - sodium, ioxynil, ioxynil - octanoate, ioxynil - potassium, and ioxynil - sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH - 043 (i.e., 3 - ({[5 - (difluoromethyl)-1 - methyl - 3 - (trifluoromethyl)-1H - pyrazol - 4 - yl]methyl}sulfonyl)-5,5 - dimethyl - 4,5 - dihydro - 1,2 - oxazole), ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA - butotyl, MCPA - dimethylammonium salt, MCPA - 2 - ethylhexyl ester, MCPA - isopropylammonium salt, MCPA - potassium salt, and MCPA - sodium salt, MCPB, MCPB - methyl ester, MCPB - ethyl ester, and MCPB - sodium salt, 2 - methyl - 4 - chlorophenoxypropionic acid (mecoprop), mecoprop - sodium, and mecoprop - butotyl, mecoprop - P, mecoprop - P - butotyl, mecoprop - P - dimethylammonium salt, mecoprop - P - 2 - ethylhexyl ester, and mecoprop - P - potassium salt, mefenacet, mefluidide, mesosulfuron, mesosulfuron - methyl, mesotrione, methabenzthiazuron, metam,Metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, 2-({2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)pyridin-3-yl}carbonyl)cyclohexane-1,3-dione, methyl isothiocyanate, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl propan-1-sulfonate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950 (i.e., N-[3-chloro-4-isopropylphenyl]-2-methylpentanamide), NGGC-011, napropamide, NC-310 (i.e., [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)methanone), neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, pethoxamid, mineral oil, phenmediphamPicloram, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron, Primisulfuron-Methyl, Prodiamine, Profoxydim, Prometon, Prometryn, Propachlor, Propanil, Propaquizafop, Propazine, Propham, Propisochlor, Propoxycarbazone, Propoxycarbazone-Sodium, Propyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen, Pyraflufen-Ethyl, Pyrasulfotole, Pyrazolynate (Pyrazolate), Pyrazosulfuron, Pyrazosulfuron-Ethyl, Pyrazoxyfen, Pyribambenz, Pyribambenz-Isopropyl, Pyribambenz-Propyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyriminobac, Pyriminobac-Methyl, Pyrimisulfan, Pyrithiobac, Pyrithiobac-Sodium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop, Quizalofop-Ethyl, Quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM-201, QYR-301, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine,Trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline).

[1213] Examples of plant growth regulators are:

[1214] Activated ester (acibenzolar), benzothiadiazole, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolid, catechine, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propanoic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium and endothal mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flamprop-M, flamprop-isopropyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthoxyacetic acid, nitrophenolate-mixture, paclobutrazol, N-(2-phenylethyl)-β-alanine, N-phenylphthalamic acid, prohexadione, calcium prohexadione, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[1215] Examples of safeners that can be mixed with the compounds of formula (I) and the compositions of the present invention are, for example, 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 (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[1216] Examples of nitrification inhibitors that can be mixed with the compounds of formula (I) and the compositions of the present invention are selected from: 2-(3,4-dimethyl-1H-pyrazol-1-yl)succinic acid, 2-(4,5-dimethyl-1H-pyrazol-1-yl)succinic acid, pyrazolium glycolate 3,4-dimethyl ester, pyrazolium citrate 3,4-dimethyl ester, pyrazolium lactate 3,4-dimethyl ester, pyrazolium mandelate 3,4-dimethyl ester, 1,2,4-triazole, 4-chloro-3-methylpyrazole, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)acetamide, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)formamide, N-((3(5),4-dimethylpyrazol-1-yl)methyl)formamide, N-((4-chloro-3(5)-methyl-pyrazol-1-yl)methyl)formamide; reaction adducts of dicyandiamide, urea and formaldehyde, triazolyl-formaldehyde-dicyandiamide adducts, 2-cyano-1-((4-oxo-1,3,5-triazinane-1-yl)methyl)guanidine, 1-((2-cyanoguanidino)methyl)urea, 2-cyano-1-((2-cyanoguanidino)methyl)guanidine, 2-chloro-6-(trichloromethyl)-pyridine (nitrapyrin or N-serve), dicyandiamide, 3,4-dimethylpyrazole phosphate, 4,5-dimethylpyrazole phosphate, 3,4-dimethylpyrazole, 4,5-dimethylpyrazole, ammonium thiosulfate, neem, products based on neem, linoleic acid, α-linolenic acid components, methyl p-coumarate, methyl ferulate, methyl 3-(4-hydroxyphenyl)propionate, piscidic acid, brachialacton, p-benzoquinone sorgoleone, 4-amino-1,2,4-triazole hydrochloride, 1-amino-2-thiourea, 2-amino-4-chloro-6-methylpyrimidine, 2-mercapto-benzothiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (chlorozole, etridiazole), 2-sulfanilamidothiazole, 3-methylpyrazole, 1,2,4-triazole thiourea, cyanamide, melamine, zeolite powder, catechol, benzoquinone, sodium tetraborate, allylthiourea, chlorates and zinc sulfate.

[1217] The compounds of formula (I) and the compositions of the present invention can be combined with one or more agriculturally beneficial agents.

[1218] Examples of agriculturally beneficial agents include: biostimulants, plant growth regulators, plant signaling molecules, growth promoters, microbial stimulatory molecules, biomolecules, soil conditioners, nutrients, plant nutrient enhancers, etc., such as lipid-chitosan oligosaccharides (LCO), chitosan oligosaccharides (CO), chitin compounds, flavonoids, jasmonic acid or its derivatives (e.g., jasmonates), cytokinins, plant growth hormones, gibberellins, abscisic acid, ethylene, brassinosteroids, salicylates, macro- and micronutrients, linoleic acid or its derivatives, linolenic acid or its derivatives, karrikins, and beneficial microorganisms (e.g., Rhizobium, Bradyrhizobium, Sinorhizobium spp., Azorhizobium spp., Glomus, Gigaspora, Hymenoscyphous spp., Oidiodendron spp., Laccaria, Pisolithus spp., Scleroderma, Rhizoctonia spp., Acinetobacter spp., Arthrobacter spp., Arthrobotrys spp., Aspergillus spp., Azospirillum, Bacillus spp., Burkholderia, Candida spp., Chryseomonas spp., Enterobacter spp., Eupenicillium spp., Exiguobacterium spp., Klebsiella spp., Kluyvera spp., Microbacterium spp., Mucor spp., Paecilomyces spp., Paenibacillus spp., Penicillium spp., Pseudomonas, Serratia spp., Stenotrophomonas spp., Streptomyces, Streptosporangium spp., Swaminathania spp., Thiobacillus spp., Torulospora spp., Vibrio spp., Xanthobacter spp.) (Xanthomonas spp., etc.), and combinations thereof.

[1219] Methods and uses

[1220] The compounds of formula (I) and the compositions of the present invention have potential microbicidal activity and / or plant defense regulating potential. They can be used to control unwanted microorganisms on plants, such as unwanted fungi and bacteria. In particular, they are used for crop protection (they control microorganisms that cause diseases to plants) or for protecting materials described in more detail below (such as industrial materials, wood, stored goods). More specifically, the compounds of formula (I) and the compositions of the present invention can be used to protect seeds, germinating seeds, newly emerged seedlings, plants, plant parts, fruits, harvested items, and / or the soil in which the plants grow from being invaded by unwanted microorganisms.

[1221] As described herein Control (Control or controlling) includes prophylactic treatment, therapeutic treatment, and eradicative treatment of unwanted microorganisms. Unwanted microorganisms May be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes, or pathogenic fungi, more specifically plant pathogenic bacteria, plant pathogenic viruses, plant pathogenic oomycetes, or plant pathogenic fungi. As described in more detail below, these plant pathogenic microorganisms are causative agents of a broad spectrum of plant diseases.

[1222] More specifically, the compounds of formula (I) and the compositions of the present invention can be used as fungicides. For the purposes of the present invention, the term "fungicide" refers to a compound or composition that can be used in crop protection to control unwanted fungi and / or control oomycetes, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes.

[1223] The compounds of formula (I) and the compositions of the present invention can also be used as antibacterial agents. In particular, they can be used in crop protection, for example, to control unwanted bacteria, such as Pseudomonadaceae, Rhizobiaceae, Xanthomonadaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae.

[1224] The compounds of formula (I) and the compositions of the present invention can also be used as antiviral agents in crop protection. For example, the compounds of formula (I) and the compositions of the present invention can have an effect on diseases caused by pl...

Claims

1. Compounds of formula (I), and their salts wherein T is O or S, n is 0 or 1, m is 0 or 1, A is N or CR 8 , wherein R 8 is hydrogen or methyl, R 1 is hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy or -C(=O)R 10 , where R 10 is methyl or ethyl, R 2 and R 3 is hydrogen, R 4 and R 5 are independently hydrogen, fluorine, methyl or ethyl, or R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## wherein wherein **For the point connected to N(R 1 ), ## For the point connected to R 6 connection point and R 3 and R 5 is hydrogen, R 6 is tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzothiazolyl, phenoxy or benzyloxy, wherein tetrahydronaphthyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxanyl, tetrahydrobenzothienyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzothiazolyl, phenoxy or benzyloxy is optionally substituted with 1 to 3 R 6S substituents, wherein R 6S independently being halogen, cyano, oxo, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C5-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl or -C(=O)R 16 , wherein R 16 is a C1-C4-alkyl group, Ring Y together with the pyridine ring or pyridazine ring respectively forms a group of formula (II-a), (II-b), (II-g), (II-h), (II-j), (II-r), (II-s), (II-u) or (II-v), wherein * is the point of attachment to the group -O-Q, # a point connected to -N(R 1 ) p is 0, 1 or 2, x1 is 1 or 2, x2 is 0, 1 or 2, G is O or NR 7L , wherein R 7L is hydrogen, R 7A is hydrogen, R 7B is hydrogen, fluorine, methyl or methoxy, R 7C is hydrogen, fluorine, methyl or methoxy, R 7D is hydrogen, R 7E is hydrogen, R 7F is hydrogen, and R 7K is a hydroxyl group or a methyl group, Q is phenyl, pyridyl or pyrimidinyl, wherein the phenyl, pyridyl, and pyrimidinyl are each optionally substituted by one or two Q substituents independently selected from the following: S halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, cyclopropyl, and cyclobutyl.

2. The compound of formula (I) according to claim 1, wherein n is 0 or 1, m is 0 or 1, R 2 and R 3 is hydrogen, R 4 and R 5 are independently hydrogen, fluorine, methyl or ethyl, or R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## wherein wherein **For the point connected to N(R 1 ), and ## The point connected to R 6 ​ 3. The compound of formula (I) according to claim 1 or 2, wherein n is 0 or 1, m is 0, and R 6 is phenyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, phenoxy or benzyloxy, Among them, Phenyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, phenoxy or benzyloxy is optionally substituted by 1 or 2 substituents R 6S substituted, wherein R 6S independently is halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl or -C(=O)R 16 , wherein R 16 is a C1-C4-alkyl group.

4. The compound of formula (I) according to claim 1, wherein Q is phenyl or pyridyl, Among them, The phenyl and pyridyl groups are optionally substituted by 1 or 2 substituents Q independently selected from the following S substituents: halogen, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, cyclopropyl and cyclobutyl.

5. A composition for controlling phytopathogenic harmful fungi, which comprises at least one compound of formula (I) according to any one of claims 1 to 4 and at least one carrier and / or surfactant.

6. A method for controlling harmful microorganisms in crop protection and material protection, characterized in that, Applying at least one compound of formula (I) according to any one of claims 1 to 4 and / or the composition according to claim 5 to harmful microorganisms and / or their habitats.

7. Use of one or more compounds of formula (I) according to any one of claims 1 to 4 and / or a composition according to claim 5 for controlling harmful microorganisms in crop protection and material protection.

8. A method for preparing a compound of formula (I), the method comprising reacting a compound of formula (1) with an amine of formula (2) or its salt to prepare the compound of formula (I), Among them, m, n, p, A, Q, Y, R in formula (I) 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 as defined in any one of claims 1 to 4, and T is O, wherein, p, A, Q, Y, and R in formula (1) 7 are as defined in any one of claims 1-4, and T is O, U 1 is a hydroxyl group, a halogen or a C1-C6-alkoxy group, Among them, m, n, R in formula (2) 1 , R 2 , R 3 , R 4 , R 5 and R 6 are defined as in any one of claims 1-4.

9. A method for preparing a compound of formula (I), the method comprising reacting a compound of formula (3) with a compound of formula (4) in the presence of a base and optionally in the presence of a transition metal catalyst and, if appropriate, in the presence of a ligand to prepare the compound of formula (I), Among them, m, n, p, A, Q, Y, R in formula (I) 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 as defined in any one of claims 1 to 4, and T is O, Among them, m, n, A, Y, R in formula (3) 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined as in any one of claims 1-4, and X 1 is a halogen, T is O, wherein Q in formula (4) is as defined in any one of claims 1 - 4.

10. The method according to claim 9, wherein the transition metal catalyst is a copper salt or complex.

11. Compounds of formula (1), and their salts, wherein A, Y, p, R 7 and Q are as defined in any one of claims 1 - 4 U 1 is a hydroxyl group, a halogen or a C1-C6-alkoxy group.

12. Compounds of formula (3), and their salts, wherein X 1 is a halogen, T is O, m, n, p, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 as defined in any one of claims 1 - 4.

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