Pyridine(thio)amides as fungicidal compounds

Abstract

The present disclosure relates to pyridine(thio)amide compounds, methods and intermediates for their preparation, and their use for controlling phytopathogenic microorganisms such as phytopathogenic fungi.

Description

Field of the Invention

[0001] The present invention relates to pyridine(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. Background Art

[0002] To date, many crop protection agents have been developed for combating or preventing 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, that 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] Substituted benzylformamides as herbicides are disclosed in WO 2005 / 070889. Phenoxypyridylformamides as GPBAR1 agonists for the treatment of diabetes are described in WO 2010 / 049302. Phenylformamides as sodium channel modulators are described in WO 2019 / 014352. N-[2-(2-pyridyl)ethyl]formamide derivatives as fungicides are disclosed in WO 2004 / 074280. Detailed Embodiments

[0005] Compound of formula (I)

[0006] The present invention relates to compounds of formula (I) and their salts, N-oxides and solvates:

[0007]

[0008] T is O or S,

[0009] n is 0 or 1,

[0010] m is 0 or 1,

[0011] Provided that when n is 0 and m is 0, then R 6 is C1-C3-alkoxy or C1-C3-haloalkoxy, wherein the C1-C3-alkoxy or C1-C3-haloalkoxy is substituted as defined for R 6 as defined,

[0012] R 1is hydrogen, hydroxy, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 , -S(=O)2R 12 ,

[0013] , -C(=O)N(R 13 )2 or S(=O)2N(R 14 )2,

[0014] wherein

[0015] R 10 , R 11 and R 12 are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[0016] R 13 and R 14 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[0017] 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,

[0018] or

[0019] 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,

[0020] 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,

[0021] or

[0022] 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,

[0023] or

[0024] R 2and 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,

[0025] and

[0026] R 3 and R 5 are independently hydrogen or halogen,

[0027] or

[0028] R 2 and R 4 together form a group of the formula **-C(R 3 )=C(R 5 )- ## ,

[0029] wherein

[0030] ** is the point of attachment to N(R 1 ),

[0031] ## is the point of attachment to R 6 ,

[0032] and

[0033] R 3 and R 5 are independently hydrogen or C1-C6-alkyl,

[0034] R 6 is C3-C 12 -carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclyloxy, C6-C 14 -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 independently substituted by one substituent selected from C3-C 12 -carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic and 5- to 14-membered heteroaryl,

[0035] wherein said C3-C 12 -carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic and 5- to 14-membered heteroaryl are optionally further substituted by one to four R 6s substituents,

[0036] wherein C3-C 12 -carbocyclic, C6-C 14-aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl group, C3-C 12 -carbocyclic ring oxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy and 3- to 14-membered heterocyclic ring oxy are optionally substituted by one to four R 6s substituents,

[0037] wherein

[0038] R 6S is independently 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, 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,

[0039] 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 also optionally substituted by one to three 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,

[0040] and

[0041] 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 also optionally substituted by one to four 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,

[0042] or

[0043] two substituents C1-C6-alkyl attached to the same carbon atom form a C3-C8-cycloalkyl ring,

[0044] or

[0045] two R 6S substituents optionally together with the carbon atom to which they are attached form a C3-C8-cycloalkyl ring,

[0046] and wherein

[0047] R 15 is hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0048] wherein the C1-C6-alkyl is also optionally substituted by one to three 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,

[0049] and

[0050] wherein the C3-C8-cycloalkyl is also optionally substituted by one to four 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,

[0051] R 16 、R 17 、R 18 and R 19 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0052] wherein the C1-C6-alkyl or C1-C6-haloalkyl is also optionally substituted by one to three 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, R 7 is hydrogen, halogen, cyano, isocyano, hydroxy, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, 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-C6-cycloalkenyl, C6-C 14-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkyloxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclic oxy group, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 20 )2, -C(=NR 21 )R 22 , -NR 23 C(=O)R 24 , -C(=O)(OR 25 ), -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2 or -S(=O)(=NR 28 )R 29 ,

[0053] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents,

[0054] wherein C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkyloxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocyclic oxy group are optionally substituted by one to three R 7Sc substituents,

[0055] and wherein

[0056] R 20 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14-aryl, 5- or 6-membered heteroaryl, or 3- to 7-membered heterocyclic group,

[0057] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl are optionally substituted with one to three substituents R 7Sa substituted,

[0058] and

[0059] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, and 3- to 7-membered heterocyclic group are optionally substituted with one to three substituents R 7Sc substituted,

[0060] R 21 and R 22 are independently hydrogen, hydroxy, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino, or di-(C1-C6-alkyl)amino,

[0061] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino, or di-(C1-C6-alkyl)amino is optionally substituted with one to three R 7Sa substituents,

[0062] R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, and C3-C8-cycloalkyl,

[0063] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted with one to three R 7Sa substituents,

[0064] and

[0065] wherein the C3-C8-cycloalkyl is optionally substituted with one to three R 7Sc substituents,

[0066] wherein

[0067] R 7Saindependently is cyano, hydroxy, carboxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C6-C 14 -aryl or a 3- to 7-membered heterocyclic group,

[0068] R 7Sc independently is halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 or a 3- to 7-membered heterocyclic group,

[0069] or

[0070] two Rs bonded to the same carbon atom 7Sc substituent C1-C6-alkyls together form C3-C8-cycloalkyl,

[0071] R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxy, mercapto, carboxy, C1-C6-alkoxycarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C 14 -aryl, a 3- to 14-membered heterocyclic group, a 5- to 14-membered heteroaryl, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, a 3- to 14-membered heterocyclic group oxy, a 5- to 14-membered heteroaryl oxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 30 )2, -SR 31 , -S(=O)R 31 or -S(=O)2R 31 ,

[0072] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, 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 one to three R 8Sa substituents,

[0073] the C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C8-cycloalkoxy, C6-C 14 -aryloxy and 3- to 14-membered heterocyclic oxy group and 5- to 14-membered heteroaryloxy group are optionally substituted by 1 to 3 R 8Sc substituents,

[0074] and wherein

[0075] R 30 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclic group,

[0076] wherein

[0077] the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are further optionally substituted by one to three R 8Sa substituents,

[0078] the C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclic group are further optionally substituted by one to three R 8Sc substituents,

[0079] R 31is C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclic group,

[0080] wherein

[0081] the C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are each optionally substituted with one to three R 8Sa substituents,

[0082] the C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclic group are each optionally substituted with one to three R 8Sc substituents,

[0083] and wherein

[0084] R 8Sa is independently selected from cyano, amino, nitro, hydroxy, formyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, 3- to 7-membered heterocyclic group and -N(R 32 )2,

[0085] wherein

[0086] the 3- to 7-membered heterocyclic group is optionally substituted with one to three C1-C6-alkyl substituents which may be the same or different,

[0087] R 32 is hydrogen, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C1-C6-alkylcarbonyl,

[0088] R 8Scindependently 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, C2-C6-alkenyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0089] wherein

[0090] said 3- to 7-membered heterocyclic group is optionally substituted by one to three substituents which may be the same or different and are C1-C6-alkyl,

[0091] or

[0092] two R 8Sc substituents optionally together with the carbon atom to which they are attached form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclic group ring,

[0093] wherein said 3- to 7-membered heterocyclic group ring is optionally substituted by one to three substituents which may be the same or different and are C1-C6-alkyl,

[0094] R 9 is hydrogen, halogen, cyano or C1-C4-alkyl,

[0095] Q is phenyl, azulenyl, naphthyl, C3-C 12 carbocyclic ring, 3- to 14-membered heterocyclic group or 5- to 14-membered heteroaryl,

[0096] wherein the phenyl is substituted by one to five substituents Q S substituted,

[0097] and

[0098] wherein azulenyl, naphthyl, C3-C 12 carbocyclic ring, 3- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl are optionally substituted by one to five substituents Q S substituted,

[0099] wherein

[0100] Q Sindependently selected from 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-C 6- 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, phenyl, naphthyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -O-C(=O)R 33 , -NR 34 C(=O)R 35 , -C(=O)N(R 36 )2, C(=S)R 37 , -C(=S)N(R 38 )2, -C(=NR 39 )R 40 , -C(=NOR 41 )R 42 and -N(R 43 )2,

[0101] wherein

[0102] 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-C 6-A haloalkenyl group, a C2-C6-alkynyl group, a C2-C6-haloalkynyl group, a C2-C6-alkenyloxy group, a C2-C6-haloalkenyloxy group, a C1-C6-alkylthio group, a C1-C6-haloalkylthio group, a C1-C6-alkylsulfinyl group, a C1-C6-haloalkylsulfinyl group, a C1-C6-alkylsulfonyl group, a C1-C6-haloalkylsulfonyl group, -O-Si(C1-C6-alkyl)3 and -Si(C1-C6-alkyl)3 are optionally substituted by one to three substituents independently selected from a cyano group, an amino group, a nitro group, a hydroxy group, a C1-C6-alkoxy group, a C1-C6-haloalkoxy group, a C1-C6-alkoxycarbonyl group, a C1-C6-haloalkoxycarbonyl group, a C3-C8-cycloalkyl group, a C3-C8-halocycloalkyl group, -Si(C1-C6-alkyl)3 and a 3- to 7-membered heterocyclic group.

[0103] The C3-C8-cycloalkyl group, the C3-C8-cycloalkoxy group, the C3-C6-cycloalkenyl group, the 3- to 7-membered heterocyclic group, the phenyl group, the naphthyl group and the 5- to 14-membered heteroaryl group are optionally substituted by one to three substituents independently selected from a halogen atom, a cyano group, an amino group, a nitro group, a hydroxy group, a formyl group, a carboxyl group, an oxo group, a methylene group, a halomethylene group, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C1-C6-alkoxy group, a C1-C6-haloalkoxy group, a C1-C6-alkoxycarbonyl group, a C1-C6-haloalkoxycarbonyl group, a C3-C8-cycloalkyl group, a C3-C8-halocycloalkyl group, a C2-C6-alkenyl group and a 3- to 7-membered heterocyclic group.

[0104] Wherein the C3-C8-cycloalkyl group, the C3-C8-halocycloalkyl group and the 3- to 7-membered heterocyclic group are optionally substituted by two substituents, and the two substituents together with the carbon atom to which they are attached form a C3-C8-cycloalkyl group.

[0105] R 34 、R 35 、R 36 、R 37 、R 38 、R 39 、R 40 、R 41 and R 42 are independently hydrogen, a C1-C6-alkyl group, a C1-C6-haloalkyl group or a C1-C6-alkoxy group.

[0106] Wherein

[0107] The C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy are optionally substituted by one to three 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,

[0108] and wherein

[0109] R 43 is independently hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl,

[0110] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted by one to three 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, and wherein the C3-C8-cycloalkyl is optionally substituted by one to three 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,

[0111] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic groups are in turn optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0112] provided that the compound of formula (I) is not:

[0113] 3-chloro-N-[4-(methylthio)benzyl]-5-(tetrahydrofuran-2-yloxy)isonicotinamide.

[0114] 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.

[0115] 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.

[0116] 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 the soil in which the plant grows.

[0117] The present invention also relates to methods and intermediates for preparing the compounds of formula (I).

[0118] Unless otherwise indicated, the following definitions apply to the substituents and residues used in this specification and the claims:

[0119] As used herein, the term "halogen" means a fluorine, chlorine, bromine or iodine atom.

[0120] As used herein, the term "methylene" means a CH2 group attached to a carbon atom by a double bond.

[0121] As used herein, the term "halomethylene" means a CX2 group attached to a carbon atom by a double bond, where X is halogen.

[0122] As used herein, the term "oxo" means an oxygen atom bonded to a carbon atom or a sulfur atom by a double bond.

[0123] As used herein, the term "C1-C6-alkyl" means a saturated branched or straight-chain 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.

[0124] As used herein, the terms "C3-C8-cycloalkyl" and "C3-C8-cycloalkyl ring" refer to a saturated monocyclic hydrocarbon ring having 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.

[0125] As used herein, the term "C2-C6-alkenyl" refers to an unsaturated branched or straight-chain 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, ethenyl (or "vinyl"), 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.

[0126] 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.

[0127] As used herein, the term "C1-C6-haloalkyl" refers to a C1-C6-alkyl as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which 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-difluoroethyl, 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.

[0128] As used herein, the term "C1-C6-fluoroalkyl" refers to a C1-C6-alkyl as defined above, wherein one or more hydrogen atoms are replaced by one or more fluorine atoms which 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.

[0129] As used herein, the term "C2-C6-haloalkenyl" means a C2-C6-alkenyl as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0130] As used herein, the term "C2-C6-haloalkynyl" means a C2-C6-alkynyl as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0131] As used herein, the term "C1-C6-alkoxy" means a group of the formula (C1-C6-alkyl)-O-, wherein 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 elsewhere, this definition also applies to alkoxy as part of a complex substituent (such as alkoxyalkyl, alkoxyalkoxy).

[0132] As used herein, the term "C1-C6-haloalkoxy" means a C1-C6-alkoxy as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which 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.

[0133] As used herein, the term "C1-C6-hydroxyalkyl" refers to a C1-C6-alkyl as defined above, wherein at least one hydrogen atom is replaced by a hydroxy group. Examples of C1-C6-hydroxyalkyl include, but are not limited to, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 1-hydroxypropyl, 1-hydroxyprop-2-yl, 2-hydroxyprop-2-yl, 2,3-dihydroxypropyl, and 1,3-dihydroxyprop-2-yl.

[0134] As used herein, the term "C3-C8-cycloalkyloxy" refers to a monocyclic saturated cycloalkyloxy having 3 to 8 and preferably 3 to 6 carbon ring members, such as (but not limited to) cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy. Unless otherwise defined elsewhere, this definition also applies to cycloalkyloxy as part of a complex substituent (such as cycloalkyloxyalkyl).

[0135] As used herein, the term "C3-C8-halocycloalkyloxy" refers to a C3-C8-cycloalkyloxy as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different.

[0136] As used herein, the term "C2-C6-alkenyloxy" refers to the formula (C2-C6-alkenyl)-O-, where the term "C1-C6-alkenyl" is as defined herein.Examples of C2-C6 alkenyl groups include, but are not limited to, ethenyloxy (or “vinyloxy”), prop-2-en-1-yloxy (or “allyl”), prop-1-en-1-yloxy, 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-yloxy (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-propylethyloxy, 1-isopropylethyloxy, 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)ethyloxy, but-1,3-dienyloxy, pent-1,4-dienyloxy, hex-1,5-dienyloxy or methylhexadienyloxy.

[0137] As used herein, the term "C2-C6-haloalkenyloxy" means (C2-C6-alkenyl)-O-, as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0138] As used herein, the term "C1-C6-alkylthio" means a saturated straight-chain or branched-chain 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.

[0139] As used herein, the term "C1-C6-haloalkylthio" means C1-C6-alkylthio as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0140] As used herein, the term "C3-C8-cycloalkylthio" means a saturated monovalent monocyclic hydrocarbon ring having 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.

[0141] As used herein, the term “C1-C6-alkylsulfinyl” refers to a saturated straight-chain or branched-chain group of the formula (C1-C6-alkyl)-S(═O)-, wherein the term “C1-C6-alkyl” is as defined herein. Examples of C1-C6-alkylsulfinyl include, but are not limited to, saturated straight-chain or branched-chain 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.

[0142] As used herein, the term “C1-C6-haloalkylsulfinyl” refers to a C1-C6-alkylsulfinyl as defined above, wherein one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0143] As used herein, the term “C3-C8-cycloalkylsulfinyl” refers to a saturated monovalent monocyclic hydrocarbon ring having 3, 4, 5, 6, 7 or 8 carbon atoms and bonded to the backbone via an -S(═O)- group. Examples of monocyclic C3-C8-cycloalkylsulfinyl include, but are not limited to, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, cycloheptylsulfinyl or cyclooctylsulfinyl.

[0144] As used herein, the term "C1-C6-alkylsulfonyl" refers to a saturated straight-chain or branched-chain 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.

[0145] As used herein, the term "C1-C6-haloalkylsulfonyl" refers to a C1-C6-alkylsulfonyl as defined above, where one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0146] As used herein, the term "C3-C8-cycloalkylsulfonyl" refers to a saturated monovalent monocyclic hydrocarbon ring having 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.

[0147] As used herein, the term "C1-C6-alkylcarbonyl" refers to a saturated straight-chain or branched-chain group of the formula (C1-C6-alkyl)-C(=O)-, where the term "C1-C6-alkyl" is as defined herein.

[0148] As used herein, the term "C1-C6-haloalkylcarbonyl" refers to a C1-C6-alkylcarbonyl as defined above, where one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0149] As used herein, the term "C1-C6-alkoxycarbonyl" refers to a saturated straight-chain or branched-chain group of the formula (C1-C6-alkoxy)-C(=O)-, where the term "C1-C6-alkoxy" is as defined herein.

[0150] As used herein, the term "C1-C6-haloalkoxycarbonyl" refers to a C1-C6-alkoxycarbonyl as defined above, where one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0151] As used herein, the term "mono-(C1-C6-alkyl)amino" refers to an amino group having one C1-C6-alkyl as defined above. Examples of mono-(C1-C6-alkyl)amino include, but are not limited to, N-methylamino, N-ethylamino, N-isopropylamino, N-n-propylamino, N-isopropylamino and N-tert-butylamino.

[0152] As used herein, the term "di-(C1-C6-alkyl)amino" refers to an amino group having two independently selected C1-C6-alkyls as defined herein. Examples of C1-C6-dialkylamino include, but are not limited to, N,N-dimethylamino, N,N-diethylamino, N,N-diisopropylamino, N-ethyl-N-methylamino, N-methyl-N-n-propylamino, N-isopropyl-N-n-propylamino and N-tert-butyl-N-methylamino.

[0153] As used herein, the term "C3-C 12 -carbocycle" refers to a saturated or partially unsaturated hydrocarbon ring system, where 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 -carbocycle includes, but is not limited to, C3-C 12 -cycloalkyl (monocyclic or bicyclic), C3-C 12 -cycloalkenyl (monocyclic or bicyclic), a bicyclic system (such as tetrahydronaphthyl, indanyl) containing an aryl (such as phenyl) fused to a monocyclic C3-C8-cycloalkyl, a bicyclic system (such as indene, dihydronaphthyl) containing an aryl (such as phenyl) fused to a monocyclic C3-C8-cycloalkenyl, and a tricyclic system containing a cyclopropyl attached via one carbon atom to a bicyclic system which contains an aryl (such as phenyl) fused to a C3-C8-cycloalkyl or C3-C8-cycloalkenyl. The C3-C 12 -carbocycle may be attached to the parent molecular moiety through any carbon atom.

[0154] As used herein, the term "C3-C 12"-Cycloalkenyl" means an unsaturated monovalent monocyclic or bicyclic hydrocarbon ring containing 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms and one or two double bonds. Examples of monocyclic C3-C8-cycloalkenyl include but are not limited to cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl. 12 Examples of bicyclic C6-C

[0155] -cycloalkenyl include but are not limited to bicyclo[2.2.1]hept-2-enyl or bicyclo[2.2.2]oct-2-enyl. 14 As used herein, the term "C6-C

[0156] As used herein, the term "3- to 14-membered heterocyclic group" refers to a saturated or partially unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13- or 14-membered 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 6- to 14-membered polycyclic (e.g., bicyclic or tricyclic) heterocycles. The 3- to 14-membered heterocyclic group can be attached 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-dioxolyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl; 6-membered rings such as piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothienyl, dithianyl, morpholinyl, 1,2-oxazinanyl, oxathianyl, thiomorpholinyl; or 7-membered rings such as oxepanyl, azepanyl, 1,4-diazepanyl and 1,4-oxazepanyl. Examples of unsaturated heterocycles include, but are not limited to, 5-membered rings such as dihydrofuryl, 1,3-dioxolyl, dihydrothienyl, pyrroline, dihydroimidazole, dihydropyrazole, isoxazoline, dihydrooxazole, dihydrothiazole; or 6-membered rings such as pyranyl, thianyl, thiazine and thiadiazine. 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. When two monocyclic heterocycles containing nitrogen atoms or a monocyclic heterocycle and a monocyclic heteroaryl are fused, the nitrogen atom can be located at the bridge (such as 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 cycloalkyl attached to the bicyclic heterocycle through a shared atom.

[0157] As used herein, the terms "3- to 7-membered heterocyclic group" and "3- to 7-membered heterocyclic ring" refer to saturated 3-, 4-, 5-, 6- or 7-membered ring systems that contain 1 or 2 heteroatoms independently selected from oxygen, nitrogen and sulfur. Examples include, but are not limited to, oxiranyl, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothianyl, dithianyl, morpholinyl, 1,2-oxazepanyl, oxathiepanyl, thiomorpholinyl, oxepanyl, azepanyl, 1,4-diazepanyl and 1,4-oxazepanyl. Preferred 3- to 7-membered heterocyclic groups are oxiranyl, aziridinyl, azetidinyl, oxetanyl, tetrahydrofuranyl, 1,3-dioxolanyl, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxanyl, morpholinyl and thiomorpholinyl.

[0158] As used herein, the term "5- to 14-membered heteroaryl" refers to an aromatic ring system that contains 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 attached to the parent molecular moiety through any carbon atom or nitrogen atom contained in the heterocycle.

[0159] As used herein, the term "5- or 6-membered heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring system that contains 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.

[0160] 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 that contains 1, 2 or 3 heteroatoms independently selected from oxygen, nitrogen and sulfur. The 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 heteroaryl include, but are not limited to, 9-membered rings such as indolyl, indolizinyl, isoindolyl, benzimidazolyl, imidazopyridyl, indazolyl, benzotriazolyl, purinyl, benzofuranyl, benzothienyl, 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 bridge (such as imidazo[1,2-a]pyridyl, [1,2,4]triazolo[4,3-a]pyridyl, imidazo[1,2-a]pyridyl, imidazo[2,1-b]oxazolyl, furano[2,3-d]isoxazolyl). Examples of tricyclic aromatic heterocycles include, but are not limited to, carbazolyl, acridinyl and phenazinyl.

[0161] As used herein, the term "C3-C 12 -carbocyclyloxy", "C3-C8-cycloalkyloxy", "C6-C 14 -aryloxy", "5- to 14-membered heteroaryloxy", "3- to 14-membered heterocyclyloxy" refers to a group of the formula -O-R, where R is C3-C 12 -carbocyclic, C3-C8-cycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 14-membered heterocyclyl as defined herein, respectively.

[0162] As used herein, the term "leaving group" should be understood to mean a group that is transferred from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulphonate ("triflate") group, an alkoxy group, a methanesulphonate group, a p-toluenesulphonate group, etc.

[0163] When referring to the variables Q, T, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9When referring to variables n and m, the term "as described herein" incorporates by reference the broad definition of the variable, as well as the preferred, more preferred, and even more preferred definitions (if any).

[0164] Compounds obtained from combinations that are contrary to the natural laws and that a person skilled in the art would thus exclude based on his / her general knowledge are not covered herein. For example, ring structures with three or more adjacent oxygen atoms are excluded.

[0165] The compounds of formula (I) may suitably be in their free form, salt form, N-oxide form, or solvate form (e.g., hydrate).

[0166] 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. Thus, 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 mentioned by means of one tautomeric description shall be considered to include all tautomeric forms.

[0167] 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. Thus, the present invention also relates to all geometric isomers and all possible mixtures in all ratios.

[0168] 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 salts having agrochemical activity).

[0169] Salts having agrochemical activity include acid addition salts of inorganic acids and organic acids as well as salts of conventional bases. Examples of inorganic acids are hydrohalic acids (such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide), sulfuric acid, phosphoric acid and nitric acid, and acid salts (such as sodium hydrogen sulfate and potassium hydrogen sulfate). 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, 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 bearing one or two sulfonic acid groups, such as phenyl and naphthyl), 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 bearing one or two phosphonic acid groups, such as phenyl and naphthyl), wherein the alkyl and aryl groups may bear further substituents, such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid and the like.

[0170] A solvate of a compound or a salt thereof according to the invention is a stoichiometric composition of the compound with a solvent.

[0171] The compounds according to the invention can exist in a variety of crystalline and / or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates and hydrates.

[0172] The invention also relates to compounds of formula (I) and their salts, N-oxides and solvates, wherein

[0173] T is O or S,

[0174] n is 1,

[0175] m is 0 or 1,

[0176] R 1 is hydrogen, hydroxy, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 , -S(=O)2R 12 ,

[0177] -C(=O)N(R 13 )2 or -S(=O)2N(R 14 )2,

[0178] wherein

[0179] R 10 、R11 and R 12 are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[0180] R 13 and R 14 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[0181] 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,

[0182] or

[0183] 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,

[0184] 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,

[0185] or

[0186] 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,

[0187] or

[0188] 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,

[0189] and

[0190] R 3 and R 5 are independently hydrogen or halogen,

[0191] or

[0192] R 2 and R 4 together form the formula **-C(R 3 )=C(R 5 )- ##group,

[0193] wherein

[0194] ** is the point connected to N(R 1 ),

[0195] ## is the point connected to R 6 ),

[0196] and

[0197] R 3 and R 5 are independently hydrogen or C1-C6-alkyl,

[0198] R 6 is C3-C 12 -carbocyclic ring, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclyloxy, C6-C 14 -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 independently substituted by a substituent selected from C3-C 12 -carbocyclic ring, C6-C 14 -aryl, 3- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl,

[0199] wherein the C3-C 12 -carbocyclic ring, C6-C 14 -aryl, 3- to 14-membered heterocyclic group and 5- to

[0200] 14-membered heteroaryl are optionally substituted by one to four R 6s substituents, wherein the C3-C 12 -carbocyclic ring, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C 12 -carbocyclyloxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy and 3- to 14-membered heterocyclyloxy are optionally substituted by one to four R 6s substituents,

[0201] wherein

[0202] R 6SIndependently 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, 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,

[0203] 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 also optionally substituted by one to three 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,

[0204] and

[0205] 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 also optionally substituted by one to four substituents independently selected from 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,

[0206] or

[0207] two C1-C6-alkyl substituents attached to the same carbon atom form a C3-C8-cycloalkyl ring,

[0208] or

[0209] two R 6S substituents optionally together with the carbon atom to which they are attached form a C3-C8-cycloalkyl ring,

[0210] and wherein

[0211] R 15 is hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl,

[0212] wherein said C1-C6-alkyl is also optionally substituted by one to three 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,

[0213] and

[0214] wherein said C3-C8-cycloalkyl is also optionally substituted by one to four substituents independently selected from 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,

[0215] R 16 , R 17 , R 18 and R 19 are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl,

[0216] wherein the C1-C6-alkyl or C1-C6-haloalkyl is also optionally substituted by one to three 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,

[0217] R 7 is hydrogen, halogen, cyano, isocyano, hydroxy, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl,

[0218] C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclic group oxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 20 )2, -C(=NR 21 )R 22 , -NR 23 C(=O)R 24 , -C(=O)(OR 25 ), -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2 or -S(=O)(=NR 28 )R 29 ,

[0219] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents,

[0220] wherein C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocyclic oxy group are optionally substituted by one to three R 7Sc substituents,

[0221] and wherein

[0222] R 20 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclic group,

[0223] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are optionally substituted by one to three substituents R 7Sa substituted,

[0224] and

[0225] wherein C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted by one to three substituents R 7Sc substituted,

[0226] R 21 and R 22is independently a hydroxyl group, an amino group, a cyano group, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C1-C6-alkoxy group, a mono-(C1-C6-alkyl)amino group or a di-(C1-C6-alkyl)amino group,

[0227] wherein the C1-C6-alkyl group, the C1-C6-haloalkyl group, the C1-C6-alkoxy group, the mono-(C1-C6-alkyl)amino group or the di-(C1-C6-alkyl)amino group is optionally substituted by one to three R 7Sa substituents,

[0228] R 23 、R 24 、R 25 、R 26 、R 27 、R 28 and R 29 is independently hydrogen, a C1-C6-alkyl group, a C1-C6-haloalkyl group and a C3-C8-cycloalkyl group,

[0229] wherein the C1-C6-alkyl group and the C1-C6-haloalkyl group are optionally substituted by one to three R 7Sa substituents,

[0230] and

[0231] wherein the C3-C8-cycloalkyl group is optionally substituted by one to three R 7Sc substituents,

[0232] wherein

[0233] R 7Sa is independently a cyano group, a hydroxyl group, a carboxyl group, a C1-C6-alkoxy group, a C1-C6-haloalkoxy group, a C3-C8-cycloalkyl group, a C3-C8-halocycloalkyl group, a C1-C6-alkoxycarbonyl group, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C6-C 14 -aryl or a 3- to 7-membered heterocyclic group,

[0234] R 7Sc is independently a halogen, a cyano group, a nitro group, a hydroxyl group, a formyl group, an oxo group, a methylene group, a halomethylene group, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C1-C6-alkoxy group, a C1-C6-haloalkoxy group, a C2-C6-alkenyl group, a C3-C8-cycloalkyl group, a C3-C8-halocycloalkyl group, -O-Si(C1-C6-alkyl)3 or a 3- to 7-membered heterocyclic group,

[0235] or

[0236] two R 7Sc substituents C1-C6-alkyl groups bonded to the same carbon atom together form a C3-C8-cycloalkyl group,

[0237] R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxy, mercapto, carboxy, C1-C6-alkoxycarbonyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 3- to 14-membered heterocyclic group oxy, 5- to 14-membered heteroaryloxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 30 )2, -SR 31 ,

[0238] -S(=O)R 31 and -S(=O)2R 31 ,

[0239] wherein

[0240] the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, 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 one to three R 8Sa substituents,

[0241] the C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C3-C8-cycloalkoxy, C6-C 14-aryloxy, 3- to 14-membered heterocyclyloxy, and 5- to 14-membered heteroaryloxy are optionally substituted by one to three R 8Sc substituents,

[0242] and wherein

[0243] R 30 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 7-membered heterocyclyl,

[0244] wherein

[0245] said C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl are optionally further substituted by one to three R 8Sa substituents,

[0246] said C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, and 3- to 7-membered heterocyclyl are optionally further substituted by one to three R 8Sc substituents,

[0247] R 31 is C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 7-membered heterocyclyl,

[0248] wherein

[0249] said C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl are optionally further substituted by one to three R 8Sa substituents,

[0250] said C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, and 3- to 7-membered heterocyclyl are optionally further substituted by one to three R 8Sc substituents,

[0251] and wherein

[0252] R 8SaIndependently selected from cyano, amino, nitro, hydroxy, formyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, 3- to 7-membered heterocyclic group and -N(R 32 )2,

[0253] wherein

[0254] said 3- to 7-membered heterocyclic group is optionally further substituted by one to three identical or different C1-C6-alkyl substituents,

[0255] R 32 is hydrogen, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C1-C6-alkylcarbonyl,

[0256] R 8Sc is 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, C2-C6-alkenyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic group,

[0257] wherein

[0258] said 3- to 7-membered heterocyclic group is optionally further substituted by one to three identical or different C1-C6-alkyl substituents,

[0259] or

[0260] two R 8Sc substituents are optionally joined with the carbon atom to which they are attached to form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclic ring,

[0261] wherein said 3- to 7-membered heterocyclic ring is optionally further substituted by one to three identical or different C1-C6-alkyl substituents,

[0262] R9 is hydrogen or a halogen,

[0263] Q is a C6-C 14 -aryl, C3-C 12 -carbocycle, a 3- to 14-membered heterocyclic group or a 5- to 14-membered heteroaryl group,

[0264] wherein the C6-C 14 -aryl, C3-C 12 -carbocycle, the 3- to 14-membered heterocyclic group and the 5- to 14-membered heteroaryl group are substituted by one to five Q S substituents, and the Q S substituents are independently selected from 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-C 6- 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, phenyl, a 5- to 14-membered heteroaryl group, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -O-C(=O)R 33 , -NR 34 C(=O)R 35 , -C(=O)N(R 36 )2, -C(=S)R 37 , -C(=S)N(R 38 )2, -C(=NR 39 )R 40 , -C(=NOR 41 )R 42 and -N(R 43 )2,

[0265] wherein

[0266] 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-C 6- 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 one to three 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,

[0267] 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 one to three 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,

[0268] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are optionally further substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0269] R 34 、R 35 、R 36 、R 37 、R 38 、R 39 、R 40 、R 41 and R 42 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0270] wherein

[0271] The C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxy are optionally substituted by one to three 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,

[0272] and wherein

[0273] R 43 is independently hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl, where the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted by one to three 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,

[0274] wherein the C3-C8-cycloalkyl is optionally substituted by one to three 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,

[0275] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0276] with the proviso that the compound of formula (I) is not:

[0277] 3-chloro-N-[4-(methylthio)benzyl]-5-(tetrahydrofuran-2-yloxy)isonicotinamide.

[0278] In a preferred embodiment, the present invention relates to compounds of formula (I) and their salts, N-oxides and solvates, wherein

[0279] T is O or S,

[0280] n is 0 or 1,

[0281] m is 0 or 1,

[0282] provided that when n is 0 and m is 0, then R 6 is C1-C3-alkoxy or C1-C3-haloalkoxy, where the C1-C3-alkoxy or C1-C3-haloalkoxy is substituted as defined for R 6 is hydrogen, hydroxy, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, -C(=O)R 1 or -C(=O)(OR 10 ) 11 ),

[0283] wherein

[0284] R 10 and R 11 are independently C1-C6-alkyl,

[0285] R 2 and R 3 are independently hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or C3-C6-cycloalkyl,

[0286] or

[0287] R 2 and R 3 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0288] R 4 and R 5 are independently hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl,

[0289] or

[0290] R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0291] or

[0292] R 2 and R 4 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0293] and

[0294] R 3 and R 5is independently hydrogen or a halogen,

[0295] R 6 is indanyl, tetrahydronaphthyl, spiro[cyclopropane-1,2'-indanyl], phenyl, naphthyl, dihydrobenzofuranyl, chromanyl, isochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxinyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzoxazolyl, benzimidazolyl, benzothienyl, imidazopyridyl, quinolinyl, isoquinolinyl, phenoxy or benzyloxy,

[0296] wherein the indanyl, tetrahydronaphthyl, spiro[cyclopropane-1,2'-indanyl], phenyl, naphthyl, dihydrobenzofuranyl, chromanyl, isochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxinyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzoxazolyl, imidazopyridyl, quinolinyl, isoquinolinyl, phenoxy and benzyloxy are optionally substituted by one to three R 6S substituents,

[0297] wherein

[0298] R 6S is independently halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R 16 or -C(=O)(OR 17 ),

[0299] 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 also optionally substituted by one or two substituents independently selected from 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, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl and tetrahydropyranyl,

[0300] and

[0301] wherein the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl and tetrahydropyranyl are also optionally substituted by one or two substituents independently selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxycarbonyl,

[0302] R 16 is C1-C6-alkyl,

[0303] R 17 is hydrogen or C1-C6-alkyl,

[0304] R 7 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C6-cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 20 )2, -C(=NR 21 )R 22 , -C(=O)(OR 25 ) or -C(=O)N(R 26 )2,

[0305] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents,

[0306] wherein the C3-C6-cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted by one to three R 7Sc substituents,

[0307] wherein

[0308] R 7Saindependently is cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C1-C6-alkoxycarbonyl, -Si(C1-C6-alkyl)3, and phenyl,

[0309] R 7Sc independently is halogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy,

[0310] and wherein

[0311] R 20 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl or C3-C6-cycloalkyl, where the C3-C6-cycloalkyl is optionally substituted by one or two substituents independently selected from halogen and C1-C4-alkyl,

[0312] R 21 is hydroxy, C1-C4-alkyl or C1-C4-alkoxy,

[0313] R 22 is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl,

[0314] R 25 and R 26 independently are hydrogen or C1-C6-alkyl,

[0315] R 8 is hydrogen, halogen, 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, phenyl, naphthyl, 3- to 10-membered heterocyclic group, 5- to 10-membered heteroaryl, C3-C8-cycloalkoxy, phenoxy, naphthoxy, 3- to 10-membered heterocyclic group oxy, 5- to 10-membered heteroaryloxy or -N(R 30 )2,

[0316] wherein

[0317] 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 one to three R 8Sa substituents,

[0318] The C3-C8-cycloalkyl, phenyl, naphthyl, 3- to 10-membered heterocyclic group, 5- to 10-membered heteroaryl, C3-C8-cycloalkoxy, phenoxy, naphthoxy and 3- to 10-membered heterocyclic oxy and 5- to 10-membered heteroaryloxy are optionally substituted by 1 to 3 R 8Sc substituents, and wherein

[0319] R 30 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C3-C6-cycloalkyl or phenyl,

[0320] wherein

[0321] the C1-C6-alkyl, C2-C6-alkenyl and C2-C6-haloalkenyl are further optionally substituted by one or two R 8Sa substituents,

[0322] the C3-C6-cycloalkyl and phenyl are further optionally substituted by one or two R 8Sc substituents,

[0323] and wherein

[0324] R 8Sa is independently selected from hydroxy, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl, C1-C6-alkylthio, -O-Si(C1-C6-alkyl)3, 3- to 7-membered heterocyclic group and -N(R 32 )2,

[0325] R 32 is hydrogen, formyl, C1-C6-alkyl or C1-C6-alkylcarbonyl,

[0326] R 8Sc is independently selected from halogen, cyano, hydroxy, oxo, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl and 3- to 7-membered heterocyclic group,

[0327] wherein

[0328] the 3- to 7-membered heterocyclic group is optionally substituted by one or two substituents independently selected from C1-C4-alkyl,

[0329] or

[0330] two Rs 8Sc substituents optionally together with the carbon atom to which they are attached form a 3- to 7-membered heterocyclic group ring,

[0331] R 9 is hydrogen, halogen, cyano or methyl,

[0332] Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxoleno[4,5-b]pyridinyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, tetrahydroquinolinyl, dihydro-5H-cyclopentadieno[b]pyridinyl, dihydrobenzofuranyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furopyridinyl, thienothiophenyl or thienothiazolyl,

[0333] wherein the phenyl is substituted by one to four substituents Q S substituted,

[0334] and

[0335] wherein naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxoleno[4,5-b]pyridinyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, tetrahydroquinolinyl, dihydro-5H-cyclopentadieno[b]pyridinyl, dihydrobenzofuranyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furopyridinyl, thienothiophenyl and thienothiazolyl are optionally substituted by one to four substituents Q S substituted,

[0336] wherein

[0337] Q S is independently selected from 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, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C 6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkyl, oxetanyl, phenyl, pyrazolyl, pyridyl, and -N(R 43 )2,

[0338] wherein

[0339] the C1-C6-alkyl and C1-C6-alkoxy are optionally substituted by one or two substituents independently selected from hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, and C1-C4-haloalkoxycarbonyl,

[0340] the C3-C6-cycloalkyl, oxetanyl, phenyl, pyrazolyl, and pyridyl are optionally substituted by one or two substituents independently selected from halogen, C1-C6-alkyl, and

[0341] C1-C6-haloalkyl,

[0342] and wherein

[0343] R 43 is independently hydrogen or C1-C6-alkyl.

[0344] In an equally preferred embodiment, the present invention relates to compounds of formula (I) and their salts, N-oxides, and solvates, wherein

[0345] T is O or S,

[0346] n is 1,

[0347] m is 0 or 1,

[0348] R 1 is hydrogen, hydroxy, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, -C(=O)R 10 or -C(=O)(OR 11 ),

[0349] wherein

[0350] R 10 and R 11 are independently C1-C6-alkyl or C2-C6-alkenyl,

[0351] R 2 and R 3 are independently hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxycarbonyl or C3-C8-cycloalkyl ring,

[0352] or

[0353] R 2 and R 3 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0354] R 4 and R 5 are independently hydrogen, halogen, hydroxy, C1-C6-alkyl or C1-C6-haloalkyl, or

[0355] R 4 and R 5 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0356] or

[0357] R 2 and R 4 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring,

[0358] and

[0359] R 3 and R 5 are independently hydrogen or halogen,

[0360] R 6 is indanyl, tetrahydronaphthyl, spiro[cyclopropane-1,2'-indanyl], phenyl, naphthyl, dihydrobenzofuranyl, chromanyl, isochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxinyl, tetrahydrobenzothienyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzoxazolyl, imidazopyridyl, quinolinyl, isoquinolinyl, phenoxy or benzyloxy,

[0361] wherein indanyl, tetrahydronaphthyl, spiro[cyclopropane-1,2'-indanyl], phenyl, naphthyl, dihydrobenzofuranyl, chromanyl, isochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxinyl, tetrahydrobenzothienyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzoxazolyl, imidazopyridyl, quinolinyl, isoquinolinyl, phenoxy and benzyloxy are optionally substituted by one to three R6S substituted by a substituent,

[0362] wherein

[0363] R 6S is independently halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R 16 or -C(=O)(OR 17 ),

[0364] 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 by one or two 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 groups,

[0365] and

[0366] wherein the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl and tetrahydropyranyl are further optionally substituted by one or two substituents independently selected from halogen, C1-C6-alkyl, C1-C6-haloalkyl and C1-C6-alkoxycarbonyl,

[0367] and wherein

[0368] R 16 is C1-C6-alkyl,

[0369] R 17 is hydrogen or C1-C6-alkyl,

[0370] R 7is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 20 )2, -C(=NR 21 )R 22 , -C(=O)(OR 25 ) or -C(=O)N(R 26 )2,

[0371] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents,

[0372] wherein

[0373] R 7Sa is independently cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl and phenyl,

[0374] wherein the C3-C8-cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted by one to three R 7Sc substituents,

[0375] wherein

[0376] R 7Sc is independently halogen, hydroxy, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,

[0377] R 20 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl, wherein the C3-C8-cycloalkyl is optionally substituted by one or two substituents independently selected from halogen and C1-C6-alkyl,

[0378] R 21 is a hydroxyl group, a C1-C6-alkyl group or a C1-C6-alkoxy group,

[0379] R 22 is hydrogen, a C1-C6-alkyl group or a C1-C6-haloalkyl group,

[0380] R 25 and R 26 are independently hydrogen or a C1-C6-alkyl group,

[0381] R 8 is hydrogen, a halogen, a hydroxyl group, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C1-C6-alkoxy group, a C1-C6-haloalkoxy group, a C2-C6-alkenyl group, a C2-C6-haloalkenyl group, a C2-C6-alkynyl group, a C2-C6-haloalkynyl group, a C1-C6-alkylthio group, a C1-C6-haloalkylthio group, a C1-C6-alkylsulfinyl group, a C1-C6-haloalkylsulfinyl group, a C1-C6-alkylsulfonyl group, a C1-C6-haloalkylsulfonyl group, a C3-C6-cycloalkyl group, a phenyl group, a naphthyl group, a 4- to 10-membered heterocyclic group, a 5- to 10-membered heteroaryl group, a C3-C6-cycloalkoxy group, a phenoxy group, a naphthoxy group, a 4- to 10-membered heterocyclic group oxy group, a 5- to 10-membered heteroaryl group oxy group or -N(R 30 )2,

[0382] wherein

[0383] the C1-C6-alkyl group, C1-C6-haloalkyl group, C1-C6-alkoxy group, C1-C6-haloalkoxy group, C2-C6-alkenyl group, C2-C6-haloalkenyl group, C2-C6-alkynyl group, C2-C6-haloalkynyl group, C1-C6-alkylthio group, C1-C6-haloalkylthio group, C1-C6-alkylsulfinyl group, C1-C6-haloalkylsulfinyl group, C1-C6-alkylsulfonyl group and C1-C6-haloalkylsulfonyl group are optionally substituted with one to three R 8Sa substituents,

[0384] the C3-C6-cycloalkyl group, phenyl group, naphthyl group, 4- to 10-membered heterocyclic group, 5- to 10-membered heteroaryl group, C3-C6-cycloalkoxy group, phenoxy group, naphthoxy group, 4- to 10-membered heterocyclic group oxy group and 5- to 10-membered heteroaryl group oxy group are optionally substituted with 1 to 3 R 8Sc substituents,

[0385] R 30 is hydrogen, a C1-C6-alkyl group, a C2-C6-alkenyl group, a C2-C6-haloalkenyl group, a C3-C6-cycloalkyl group or a phenyl group,

[0386] wherein

[0387] The C1-C6-alkyl, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally substituted by one or two R 8Sa substituents,

[0388] The C3-C6-cycloalkyl and phenyl are optionally substituted by one or two R 8Sc substituents,

[0389] R 8Sa is independently selected from hydroxy, carboxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl, C1-C6-alkylthio, -O-Si(C1-C6-alkyl)3, a 3- to 7-membered heterocyclic group and -N(R 32 )2,

[0390] wherein

[0391] R 32 is hydrogen, formyl, C1-C6-alkyl or C1-C6-alkylcarbonyl,

[0392] R 8Sc is independently selected from halogen, cyano, hydroxy, oxo, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, C3-C6-cycloalkyl and a 3- to 7-membered heterocyclic group,

[0393] wherein

[0394] the 3- to 7-membered heterocyclic group is optionally substituted by one or two identical or different substituents C1-C6-alkyl,

[0395] or

[0396] two R 8Sc substituents optionally together with the carbon atom to which they are attached form a 3- to 7-membered heterocyclic group ring,

[0397] R 9 is hydrogen or halogen,

[0398] Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolano[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, dihydrobenzofuranyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furanopyridinyl, thienothiophenyl or thienothiazolyl,

[0399] wherein the phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolano[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, dihydrobenzofuranyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furanopyridinyl, thienothiophenyl and thienothiazolyl are substituted with one to four Q S substituents, and the Q S substituents are independently selected from 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-C 6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkyl, oxetanyl and -N(R 43 )2,

[0400] wherein

[0401] the C3-C6-cycloalkyl and oxetanyl are optionally further substituted with one or two substituents independently selected from halogen, C1-C4-alkyl and C1-C4-haloalkyl,

[0402] and R 43 is hydrogen and C1-C6-alkyl.

[0403] In a more preferred embodiment, the present invention relates to compounds of general formula (I) and their salts, N-oxides and solvates, wherein

[0404] T is O,

[0405] n is 1,

[0406] m is 0 or 1,

[0407] R 1 is hydrogen, cyano, C1-C4-alkyl, C1-C4-alkoxy or -C(=O)R 10 ,

[0408] wherein

[0409] R 10 is C1-C4-alkyl,

[0410] R 2 and R 3 are independently hydrogen or C1-C4-alkyl,

[0411] R 4 and R 5 are independently hydrogen, fluorine or chlorine,

[0412] R 6 is phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxenyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzimidazolyl, benzothienyl or benzyloxy,

[0413] wherein phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxenyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzimidazolyl, benzothienyl and benzyloxy are optionally substituted with one to three R 6S substituents,

[0414] wherein

[0415] R 6S is independently halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, pyridyl, -C(=O)R 16 or -C(=O)(OR 17 ),

[0416] wherein the C1-C4-alkyl and C2-C4-alkynyl are also optionally substituted by one or two substituents independently selected from hydroxy, C1-C4-alkoxy, and -Si(C1-C4-alkyl)3,

[0417] and

[0418] wherein the C3-C6-cycloalkyl, phenyl, pyrazolyl, and pyridyl are also optionally substituted by one or two substituents independently selected from fluorine, chlorine, C1-C4-alkyl, and C1-C4-haloalkyl,

[0419] R 16 is C1-C4-alkyl,

[0420] R 17 is hydrogen or C1-C4-alkyl,

[0421] R 7 is hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, imidazolyl, pyrazolyl, pyridyl, oxetanyl, tetrahydrofuranyl, pyrrolidinyl, piperidinyl, -N(R 20 )2, -C(=NR 21 )R 22 or -C(=O)(OR 25 ),

[0422] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents,

[0423] wherein the C3-C6-cycloalkyl, imidazolyl, pyrazolyl, pyridyl, oxetanyl, pyrrolidinyl, and piperidinyl are optionally substituted by one or two R 7Sc substituents,

[0424] wherein

[0425] R 7Sa is independently C1-C4-alkoxy, -Si(C1-C4-alkyl)3, or phenyl,

[0426] R 7Sc is independently halogen or C1-C4-alkyl,

[0427] and wherein

[0428] R 20 is hydrogen, C1-C4-alkyl, or C3-C6-cycloalkyl,

[0429] R 21 is a C1-C4-alkyl or a C1-C4-alkoxy group,

[0430] R 22 is hydrogen or a C1-C4-alkyl group,

[0431] R 25 is hydrogen or a C1-C4-alkyl group,

[0432] R 8 is hydrogen, halogen, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkoxy group, a C2-C4-alkenyl group, a C2-C4-alkynyl group, a C1-C4-alkylthio group, a C3-C6-cycloalkyl group, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridyl, phenoxy or -N(R 30 )2,

[0433] wherein

[0434] said C3-C6-cycloalkyl group, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridyl and phenoxy are optionally substituted with one or two R 8Sc substituents,

[0435] wherein

[0436] R 8Sc is independently selected from halogen or a C1-C4-alkyl group,

[0437] wherein

[0438] R 30 is independently hydrogen or a C1-C4-alkyl group,

[0439] R 9 is hydrogen, fluorine, chlorine or cyano,

[0440] Q is phenyl, naphthyl, indanyl, 1,3-benzodioxolyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, thienyl, pyridyl or quinolinyl,

[0441] wherein phenyl is substituted with one to three substituents Q S substituents,

[0442] and

[0443] wherein naphthyl, indanyl, 1,3-benzodioxolyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, thienyl, pyridyl and quinolinyl are optionally substituted with one to three substituents Q S substituents,

[0444] wherein

[0445] Q S is independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl, oxetanyl, phenyl, pyrazolyl, pyridyl, and -N(R 43 )2,

[0446] wherein

[0447] the C1-C4-alkyl and C1-C4-alkoxy are optionally substituted by one or two substituents independently selected from hydroxy, C1-C4-alkoxy, and C1-C4-alkoxycarbonyl,

[0448] the C3-C6-cycloalkyl, phenyl, pyrazolyl, and pyridyl are optionally substituted by one or two substituents independently selected from halogen and C1-C4-alkyl,

[0449] and wherein

[0450] R 43 is independently hydrogen or C1-C4-alkyl.

[0451] In an equally more preferred embodiment, the invention relates to compounds of formula (I) and their salts, N-oxides, and solvates, wherein

[0452] T is O,

[0453] n is 1,

[0454] m is 0 or 1,

[0455] R 1 is hydrogen, C1-C4-alkyl, C1-C4-alkoxy, or -C(=O)R 10 ,

[0456] wherein

[0457] R 10 is C1-C4-alkyl,

[0458] R 2 and R 3 are independently hydrogen or C1-C4-alkyl,

[0459] or

[0460] R 2 and R 3 together with the carbon atom to which they are attached form a C3-C5-cycloalkyl,

[0461] R 4 and R 5 are independently hydrogen or halogen,

[0462] or

[0463] R 4 and R 5 together with the carbon atom to which they are attached form a C3-C5-cycloalkyl group,

[0464] R 6 is phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, phenoxy or benzyloxy,

[0465] wherein the phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, phenoxy or benzyloxy is optionally substituted by one to three R 6S substituents,

[0466] wherein

[0467] R 6S is independently 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 or -C(=O)(OR 17 ),

[0468] wherein the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl and pyridyl are also optionally substituted by one or two substituents independently selected from fluorine, chlorine, C1-C4-alkyl and C1-C4-haloalkyl,

[0469] and wherein

[0470] R 16 is C1-C4-alkyl,

[0471] R 17 is hydrogen or C1-C4-alkyl,

[0472] R 7is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, -N(R 20 )2, -C(=NR 21 )R 22 or -C(=O)(OR 25 ),

[0473] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents,

[0474] wherein the C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl are optionally substituted by one or two R 7Sc substituents,

[0475] wherein

[0476] R 20 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl,

[0477] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[0478] R 22 is C1-C4-alkyl,

[0479] R 25 is hydrogen or C1-C4-alkyl,

[0480] and wherein

[0481] R 7Sa is independently C1-C4-alkoxy or phenyl,

[0482] R 7Sc is independently halogen or C1-C4-alkyl,

[0483] R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridyl or -N(R 30 )2,

[0484] wherein said C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl and pyridyl are optionally substituted by one or two R 8Sc substituents,

[0485] wherein

[0486] R 30 is C1-C6-alkyl,

[0487] R 8Sc independently is halogen or C1-C4-alkyl,

[0488] R 9 is hydrogen or halogen,

[0489] Q is phenyl, 2,3-dihydrobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, 2,3-dihydro-1,4-benzodioxenyl, 5,6,7,8-tetrahydroquinolinyl, 2,3-dihydrobenzofuranyl, thienyl, pyridyl or indolyl,

[0490] wherein phenyl, 2,3-dihydrobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, 2,3-dihydro-1,4-benzodioxenyl, 5,6,7,8-tetrahydroquinolinyl, 2,3-dihydrobenzofuranyl, thienyl, pyridyl and indolyl are substituted by one to three Q S substituents, Q S substituents independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkynyl, C3-C6-cycloalkyl, oxetanyl and -N(R 43 )2,

[0491] wherein

[0492] said C3-C6-cycloalkyl and oxetanyl are further optionally substituted by one or two substituents independently selected from halogen and C1-C4-alkyl,

[0493] R 43 independently is hydrogen and C1-C4-alkyl.

[0494] In an even more preferred embodiment, the present invention relates to compounds of formula (I) and their salts, N-oxides and solvates, wherein

[0495] T is O,

[0496] n is 1,

[0497] m is 0 or 1,

[0498] R 1 is hydrogen,

[0499] wherein

[0500] R 10 is C1-C4-alkyl,

[0501] R 2 and R 3 are independently hydrogen or methyl,

[0502] R 4 and R 5 are independently hydrogen or fluorine,

[0503] R 6 is phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzimidazolyl, benzothienyl or benzyloxy,

[0504] wherein the phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, benzimidazolyl, benzothienyl and benzyloxy are optionally substituted by one to three R 6S substituents,

[0505] wherein

[0506] 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, pyrazolyl, pyridyl, -C(=O)R 16 or -C(=O)(OR 17 ),

[0507] wherein the C1-C4-alkyl and C2-C4-alkynyl are also optionally substituted by one or two substituents independently selected from hydroxy, methoxy, ethoxy and trimethylsilyl,

[0508] R 16 is C1-C4-alkyl,

[0509] R 17 is C1-C4-alkyl,

[0510] R 7is chlorine, iodine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, pyrazolyl, pyridyl, tetrahydrofuranyl, pyrrolidinyl, -N(R 20 )2, -C(=NR 21 )R 22 or -C(=O)(OR 25 ),

[0511] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents,

[0512] wherein the C3-C6-cycloalkyl, pyrazolyl, pyridyl, tetrahydrofuranyl and pyrrolidinyl are optionally substituted by one or two R 7Sc substituents,

[0513] wherein

[0514] R 7Sa is independently C1-C4-alkoxy, -Si(C1-C4-alkyl)3 or phenyl,

[0515] R 7Sc is independently halogen or C1-C4-alkyl,

[0516] and wherein

[0517] R 20 is hydrogen, C1-C4-alkyl, cyclopropyl or C3-C6-ring,

[0518] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[0519] R 22 is hydrogen or C1-C4-alkyl,

[0520] R 25 is hydrogen or C1-C4-alkyl,

[0521] R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl, phenyl, pyrrolidinyl, pyrazolyl, phenoxy or -N(R 30 )2,

[0522] wherein

[0523] The C3-C6-cycloalkyl, phenyl, pyrrolidinyl, pyrazolyl and phenoxy are optionally substituted by one or two R 8Sc substituents,

[0524] wherein

[0525] R 8Sc is independently selected from halogen or C1-C4-alkyl,

[0526] wherein

[0527] R 30 is independently hydrogen or C1-C4-alkyl,

[0528] R 9 is hydrogen, fluorine, chlorine or cyano,

[0529] Q is phenyl, naphthyl, indanyl, 1,3-benzodioxolyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, thienyl, pyridyl or quinolinyl,

[0530] wherein the phenyl is substituted by one to three substituents Q S substituents,

[0531] and

[0532] wherein the naphthyl, indanyl, 1,3-benzodioxolyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, thienyl, pyridyl and quinolinyl are optionally substituted by one to three substituents Q S substituents,

[0533] wherein

[0534] Q S is independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl, oxetanyl, phenyl, pyrazolyl, pyridyl and -N(R 43 )2,

[0535] wherein

[0536] the C1-C4-alkyl and C1-C4-alkoxy are optionally substituted by one or two substituents independently selected from hydroxy, methoxy or ethoxy,

[0537] the C3-C6-cycloalkyl, phenyl, pyrazolyl and pyridyl are optionally substituted by one or two substituents independently selected from halogen and C1-C4-alkyl,

[0538] and wherein

[0539] R 43 is independently hydrogen or a C1-C4-alkyl group.

[0540] In an equally even more preferred embodiment, the present invention relates to compounds of general formula (I) and their salts, N-oxides and solvates, wherein

[0541] T is O,

[0542] n is 1,

[0543] m is 0 or 1,

[0544] R 1 is hydrogen,

[0545] R 2 and R 3 are independently hydrogen,

[0546] R 4 and R 5 are independently hydrogen or fluorine,

[0547] R 6 is phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxenyl, furanyl, pyrazolyl, thienyl, pyrimidinyl, indolyl or benzyloxy,

[0548] wherein the phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxenyl, furanyl, pyrazolyl, thienyl, pyrimidinyl, indolyl and phenoxy are optionally substituted by one to three R 6S substituents,

[0549] wherein

[0550] R 6S is independently halogen, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, vinyl, allyl, ethynyl, propargyl, C3-C6-cycloalkyl, pyrazolyl or -C(=O)(OR 17 ),

[0551] wherein the C3-C6-cycloalkyl and pyrazolyl are also optionally substituted by one or two substituents independently selected from fluorine, chlorine and C1-C4-alkyl, R 17 is hydrogen or C1-C4-alkyl,

[0552] R 7is chlorine, iodine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, -N(R 20 )2 or -C(=NR 21 )R 22 ,

[0553] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents,

[0554] wherein the C3-C6-cycloalkyl is optionally substituted by one or two R 7Sc substituents,

[0555] wherein

[0556] R 7Sa is independently C1-C4-alkoxy,

[0557] R 7Sc is independently halogen,

[0558] R 20 is hydrogen, cyclopropyl or cyclobutyl,

[0559] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[0560] R 22 is C1-C4-alkyl,

[0561] R 8 is hydrogen, halogen or C1-C4-alkyl,

[0562] R 9 is hydrogen or halogen,

[0563] Q is phenyl,

[0564] wherein the phenyl is substituted by one to three Q S substituents, Q S substituents are independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkynyl, C3-C6-cycloalkyl and oxetanyl,

[0565] wherein

[0566] The C3-C6-cycloalkyl and oxetanyl are each independently optionally substituted with one or two substituents selected from the group consisting of halogen.

[0567] Preferably, R 1 is 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 each independently C1-C6-alkyl or C2-C6-alkenyl.

[0568] More preferably, R 1 is hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy or -C(=O)R 10 , where R 10 is each independently C1-C4-alkyl.

[0569] Even more preferably, R 1 is hydrogen,

[0570] Suitable non-limiting examples of R 1 include any R 1 group disclosed in the "R 1 " column of Table 1.

[0571] Preferably, n is 1 and m is 0 or 1,

[0572] Preferably, R 2 and R 3 are each independently hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxycarbonyl or C3-C8-cycloalkyl, or R 2 and R 3 together with the carbon atom to which they are attached form a C3-C6-cycloalkyl ring.

[0573] More preferably, R 2 and R 3 are each 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.

[0574] Even more preferably, R 2 and R 3 are hydrogen.

[0575] Preferably, R 4 and R 5 are each independently hydrogen, halogen, hydroxy, C1-C6-alkyl or C1-C6-haloalkyl, or R 4 and R5 Together with the carbon atom to which they are attached, form a C3-C6-cycloalkyl ring.

[0576] More preferably, R 4 and R 5 independently are hydrogen or halogen, or R 4 and R 5 together with the carbon atom to which they are attached, form a cyclopropyl ring.

[0577] Preferably, R 2 and R 4 form a cyclopropyl ring and R 3 and R 5 independently are hydrogen or halogen.

[0578] More preferably, R 1 is hydrogen, R 2 and R 3 independently are hydrogen or C1-C4-alkyl, or R 2 and R 3 together with the carbon atom to which they are attached, form a cyclopropyl, R 4 and R 5 independently are hydrogen or halogen, or R 4 and R 5 together with the carbon atom to which they are attached, form a cyclopropyl.

[0579] Even more preferably, R 1 is hydrogen, n is 1, m is 0 or 1, R 2 and R 3 independently are hydrogen or methyl, R 4 and R 5 independently are hydrogen or halogen.

[0580] Preferably, R 6 is C7-C 12 -carbocyclic ring, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl, C6-C 14 -aryloxy and C1-C3-alkoxy substituted by a C6-C 14 -aryl, wherein

[0581] the C6-C 14 -aryl is optionally substituted by one to three substituents R 6S substituted,

[0582] wherein C7-C 12 -carbocyclic ring, C6-C 14 -aryl, 3- to 14-membered heterocyclic group, 5- to 14-membered heteroaryl and C6-C 14 -aryloxy are optionally substituted by one to three substituents R 6S substituted,

[0583] wherein

[0584] R 6S is independently 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 or -C(=O)(OR 17 ),

[0585] 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 also optionally substituted by one or two 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 groups, and wherein the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl and tetrahydropyranyl are also optionally substituted by one or two 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.

[0586] More preferably, R 6is phenyl, naphthyl, indanyl, tetrahydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-2,1'-indanyl]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroindolyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, dihydro-1,4-benzodioxenyl, tetrahydrobenzothiophenyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, 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, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, 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,

[0587] Among them, phenyl, naphthyl, indanyl, tetrahydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-triene-1-yl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, dihydroindolyl, 1,3-benzodioxolyl, tetrahydroquinolyl, chromanyl, isochromanyl, thiochromanyl, dihydro-1,4-benzodioxenyl, tetrahydrobenzothiophenyl, dihydro-5H-cyclopenta[b]pyridyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, dihydro-4H-cyclopenta[b]thiophenyl, 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, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, 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, furo[2,3-d]isoxazolyl and thieno[2,3-d]isothiazolyl are optionally substituted by one or two substituents independently selected from 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 ), where the substituent R 6S substitutes, and the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl and pyridyl are optionally further substituted by one or two substituents independently selected from fluorine, chlorine, C1-C4-alkyl and C1-C4-haloalkyl, and where R 16 is C1-C4-alkyl, R 17 is hydrogen or C1-C4-alkyl.

[0588] Even more preferably, R 6is phenyl, 1,3-benzodioxol-5-yl, 2,3-dihydro-1,4-benzodioxin-6-yl, 4,5,6,7-tetrahydrobenzothiophen-7-yl, furan-2-yl, thiophene-2-yl, thiophene-3-yl, pyrazol-1-yl, pyrimidin-2-yl, pyrimidin-5-yl, indol-3-yl, indol-4-yl, indol-5-yl, phenoxy or benzyloxy,

[0589] wherein the phenyl, 1,3-benzodioxol-5-yl, 2,3-dihydro-1,4-benzodioxin-6-yl, 4,5,6,7-tetrahydrobenzothiophen-7-yl, furan-2-yl, thiophene-2-yl, thiophene-3-yl, pyrazol-1-yl, pyrimidin-2-yl, pyrimidin-5-yl, indol-3-yl, indol-4-yl, indol-5-yl, phenoxy and benzyloxy are optionally substituted by one or two substituents R 16 or -C(=O)R 17 ) independently selected from 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 6S substituted, where the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl and pyridyl are also optionally substituted by one or two substituents independently selected from fluorine, chlorine, C1-C4-alkyl and C1-C4-haloalkyl, and where R 16 is C1-C4-alkyl and R 17 is hydrogen or C1-C4-alkyl.

[0590] In yet another even more preferred embodiment, R 6 is

[0591]

[0592] where

[0593] § 1 is the point attached to C(R 4 R 5 ) m and

[0594] R 6S1 and R 6S2 are independently hydrogen or R 6S ,

[0595] where

[0596] R 6Sis hydrogen, 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 and pyrazolyl,

[0597] wherein the C3-C6-cycloalkyl and pyrazolyl are optionally substituted by one or two substituents independently selected from halogen and C1-C4-alkyl,

[0598] with the proviso that R 6S1 and R 6S2 are at least one different from hydrogen.

[0599] Suitable non-limiting examples of the chain include any chain disclosed in the column of Table 1. chain.

[0600] Preferably, R 7 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 20 )2, -C(=NR 21 )R 22 , -C(=O)(OR 25 ) or -C(=O)(OR 26 )2, wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents, and wherein C3-C8-cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted by one to three R 7Sc substituents,

[0601] wherein

[0602] R 20 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl,

[0603] wherein the C3-C8-cycloalkyl is optionally substituted by one or two substituents independently selected from halogen and C1-C6-alkyl,

[0604] R 21 is hydroxy, C1-C6-alkyl or C1-C6-alkoxy,

[0605] R 22 is hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[0606] R 25 and R 26 are independently hydrogen or C1-C6-alkyl,

[0607] and wherein

[0608] R 7Sa is independently cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl and phenyl,

[0609] R 7Sc is independently halogen, hydroxy, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy.

[0610] More preferably, R 7 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, -N(R 20 )2, -C(=NR 21 )R 22 or -C(=O)(OR 25 ), wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents, wherein the C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl are optionally substituted by one or two R 7Sc substituents,

[0611] wherein

[0612] R 20 is hydrogen, a C1-C4-alkyl or a C3-C6-cycloalkyl,

[0613] R 21 is a C1-C4-alkyl or a C1-C4-alkoxy,

[0614] R 22 is a C1-C4-alkyl,

[0615] R 25 is hydrogen or a C1-C4-alkyl,

[0616] and wherein

[0617] R 7Sa is independently a C1-C4-alkoxy or phenyl,

[0618] R 7Sc is independently a halogen or a C1-C4-alkyl.

[0619] Likewise more preferably, R 7 is chlorine, iodine, a C1-C4-alkyl, a C1-C4-haloalkyl, a C1-C4-hydroxyalkyl, a C1-C4-alkylcarbonyl, a C1-C4-alkoxy, a C2-C4-alkenyl, a C2-C4-alkynyl, a C3-C6-cycloalkyl, -N(R 20 )2 or -C(=NR 21 )R 22 ,

[0620] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents,

[0621] wherein the C3-C6-cycloalkyl is optionally substituted by one or two R 7Sc substituents,

[0622] wherein

[0623] R 20 is hydrogen, cyclopropyl or cyclobutyl,

[0624] R 21 is a C1-C4-alkyl or a C1-C4-alkoxy,

[0625] R 22 is a C1-C4-alkyl,

[0626] and wherein

[0627] R 7Sais independently a C1-C4-alkoxy,

[0628] R 7Sc is independently a halogen.

[0629] Even more preferably, R 7 is chlorine, iodine, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl or -C(=NR 21 )R 22 ,

[0630] wherein

[0631] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[0632] R 22 is C1-C4-alkyl.

[0633] Suitable non-limiting examples of R 7 include any R 7 group listed in the "R 7 " column of Table 1.

[0634] Preferably, R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridinyl or -N(R 30 )2,

[0635] wherein the C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl and pyridinyl are optionally substituted with one or two R 8Sc substituents,

[0636] R 30 is C1-C6-alkyl,

[0637] R 8Sc is independently selected from halogen and C1-C4-alkyl.

[0638] More preferably, R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio or C3-C6-cycloalkyl.

[0639] Also more preferably, R 8 is hydrogen, halogen or C1-C4-alkyl.

[0640] Even more preferably, R 8 is hydrogen, halogen or C1-C4-alkyl.

[0641] Suitable examples of R 8 include any R 8 listed in the "R 8 " column of Table 1.

[0642] Preferably, Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxoleno[4,5-b]pyridinyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, dihydrobenzofuranyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furanopyridyl, thienothiophenyl or thienothiazolyl, where

[0643] the phenyl is substituted by one to four substituents Q S substituted,

[0644] and where naphthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxoleno[4,5-b]pyridinyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, dihydrobenzofuranyl, pyrrolyl, furyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furanopyridyl, thienothiophenyl and thienothiazolyl are optionally substituted by one to four substituents Q S substituted,

[0645] where

[0646] Q Sindependently selected from 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-C 6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-cycloalkyl, oxetanyl and -N(R 43 )2, where the C3-C6-cycloalkyl and oxetanyl are optionally substituted by one or two substituents independently selected from halogen, C1-C4-alkyl and C1-C4-haloalkyl, and where R 43 is hydrogen or C1-C6-alkyl.

[0647] More preferably, Q is phenyl, naphthyl, bicyclo[4.2.0]oct-1(6)2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridyl, thienyl or indolyl, where the phenyl is substituted by one to three substituents Q S and where the naphthyl, bicyclo[4.2.0]oct-1(6)2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridyl, thienyl and indolyl are substituted by one to three substituents Q S substituted,

[0648] where Q S is independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkynyl and C3-C6-cycloalkyl, where the C3-C6-cycloalkyl and oxetanyl are optionally substituted by one or two substituents independently selected from fluorine or methyl.

[0649] Even more preferably, Q is phenyl, where the phenyl is substituted by one or two substituents Q independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, cyclopropyl and cyclobutyl S substituted, where the cyclopropyl and cyclobutyl are optionally substituted by one or two substituents independently selected from fluorine or methyl.

[0650] Even more preferably still, Q is

[0651]

[0652] wherein

[0653] § 2 is a point connected to an oxygen atom,

[0654] Q S1 is hydrogen or a halogen,

[0655] Q S2 is hydrogen, a halogen, a cyano group, a nitro group, a C1-C4-alkyl group, a trifluoromethyl group, a difluoromethyl group, a C1-C4-alkylcarbonyl group, a C1-C6-alkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a C2-C4-alkynyl group, a C3-C6-cycloalkyl group, an oxiranyl group or an oxetanyl group,

[0656] provided that at least one of Q S1 and Q S2 is different from hydrogen.

[0657] Non-limiting examples of suitable Qs include any Q group listed in the "Q" column of Table 1.

[0658] m, n, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and the above-defined definitions of Q (broad definitions as well as preferred, more preferred, and even more preferred definitions) can be combined in various ways. Thus, the combinations of these definitions provide subclasses of the compounds according to the invention, as disclosed below, for example.

[0659] The invention also relates to any compound of formula (I) disclosed in Table 1.

[0660] 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.

[0661] Process for preparing the compound of formula (I) and intermediates

[0662] The invention relates to a method for preparing the compounds of formula (I) and their intermediates. Unless otherwise specified, the groups Q, T, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R9 , m and n 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.

[0663] The compounds of formula (I-a) to (I-g) are subsets of formula (I). The compounds of formula (I-a-1) to (I-a-8) are subsets of formula (I-a). Unless otherwise specified, all substituents of formula (I-a) to (I-g) and (I-a-1) to (I-a-8) are defined as above for formula (I).

[0664] The compounds of general formula (I) can be prepared by different routes similar to known methods (see the examples and references in this article). Non-limiting examples of suitable methods are described herein.

[0665] The compounds of formula (I) can be obtained directly by carrying out Method A or B, 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. Non-limiting examples of such transformation or derivatization are described below (Methods C to G).

[0666] The methods described herein can be appropriately carried out using one or more inert organic solvents commonly used for 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-butylnitrile or isobutylnitrile 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.

[0667] Some of the methods described herein may require or optionally employ 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, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), quinuclidine, 3-acetoxyquinuclidine, guanidine, or aromatic bases (such as pyridine, methylpyridine, dimethylpyridine, or trimethylpyridine).

[0668] 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.

[0669] Suitable copper salts or complexes and their hydrates include, but are not limited to, copper metal, copper(I) iodide, copper(I) chloride, copper(I) bromide, copper(II) chloride, copper(II) bromide, copper(II) oxide, copper(I) oxide, copper(II) acetate, copper(I) acetate, copper(I) 2-thiophenecarboxylate, copper(I) cyanide, copper(II) sulfate, copper(II) bis(2,2,6,6-tetramethyl-3,5-heptanedionate), copper(II) trifluoromethanesulfonate, copper(I) tetra(acetonitrile) hexafluorophosphate, copper(I) tetra(acetonitrile) tetrafluorophosphate.

[0670] By adding a copper salt and a ligand or salt separately to the reaction, a suitable copper complex can also be generated in-situ in the reaction mixture, and the ligand or 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'-bipyridine, 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]-cyclohexanecarboxamide, 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, ethylenebis-(diphenylphosphine), N,N-diethylsalicylamide, 2-hydroxybenzaldehyde oxime, oxo[(2,4,6-trimethylphenyl)amino]acetic acid or 1H-pyrrole-2-carboxylic acid.

[0671] 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.

[0672] Palladium complexes can also be formed in the reaction mixture by adding a palladium salt and a ligand or salt separately to the reaction, the ligand or salt being, for example, triethylphosphine, tri-tert-butylphosphine, tri-tert-butylphosphine tetrafluoroborate, tricyclohexylphosphine, 2-(dicyclohexylphosphino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-(tert-butylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexyl ... Phosphine-2,6'-dimethoxybiphenyl, 2-dicyclohexylphosphine-2',6'-diisopropoxybiphenyl, triphenylphosphine, tri-(o-tolyl)phosphine, sodium 3-(diphenylphosphine)benzenesulfonate, tri-(2-methoxy-phenyl)phosphine, 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl, 1,4-bis(diphenylphosphine)butane, 1,2-bis(diphenylphosphine)ethane, 1,4-bis(dicyclohexylphosphine)butane, 1,2-bis(dicyclohexylphosphine)-ethane, 2-(dicyclohexylphosphine)-2'-(N,N-dimethylamino)-biphenyl, 1,1'-bis(diphenylphosphine)-ferrocene,

[0673] (R)-(-)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, tris-(2,4-tert-butyl-phenyl)phosphite, di(1-adamantyl)-2-morpholinophenylphosphine or 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride.

[0674] 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).

[0675] Some of the methods described herein can be carried out by metal photoredox catalysis according to the methods recorded 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). The method is then carried out in the presence of a photosensitizer (such as Ir and Ru complexes or organic dyes) and a metal catalyst (such as Ni complex). 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.

[0676] 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 (dFppy = 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-mesityl-10-acridinium, 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.

[0677] 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).

[0678] The processes described herein can be carried out at temperatures from -105 °C to 250 °C, preferably from -78 °C to 185 °C.

[0679] The reaction time varies depending on the reaction scale and the reaction temperature, but generally ranges from a few minutes to 48 hours.

[0680] The processes described herein are generally carried out at standard pressure. However, they can also be carried out at elevated or reduced pressure.

[0681] In the processes 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.

[0682] Process for preparing the compound of formula (I)

[0683] Process A

[0684] A compound of formula (I-a), wherein m, n, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 and Q are as defined above, and

[0685] T is O, can be prepared by the following process as shown in Scheme 1, said process comprising reacting a compound of formula (1), wherein R 7 、R 8 、R 9 and Q are as defined above, and

[0686] U 1 is hydroxy, halogen or C1-C6-alkoxy, with an amine of formula (2), wherein m, n, R 1 、R2 , R 3 , R 4 , R 5 and R 6 react as defined above, or a step of reacting with its salt.

[0687] Scheme 1: Method A - Synthesis of Amides of Formula (I-a)

[0688]

[0689] wherein U 1 is a hydroxyl group, and the compound of formula (1) can react with the amine of formula (2) in the presence of a condensation reagent by the method described in the literature (such as Tetrahedron 2005, 61, 10827-10852). Examples of suitable condensation reagents include, but are not limited to, halogenating reagents (such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride or thionyl chloride), dehydrating agents (such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride), carbodiimides (such as N,N'-dicyclohexylcarbodiimide (DCC)) or other conventional condensation (or peptide coupling) reagents (such as 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, tripyrrolidinylphosphonium bromide hexafluorophosphate or propylphosphonic anhydride (T3P)).

[0690] wherein U 1 is a halogen atom, and the compound of formula (1) can react with the amine of formula (2) in the presence of an acid scavenger by a well-known method. Suitable acid scavengers include any inorganic and organic bases commonly used in this reaction as described herein. Preferably alkali metal carbonates, alkaline earth metal acetates, tertiary amines or aromatic bases.

[0691] wherein U 1 is a C1-C6-alkoxy group, and the compound of formula (1) can react with an excess of the amine of formula (2), optionally in the presence of a Lewis acid (such as trimethylaluminum).

[0692] The compound of formula (1) can be prepared by one or more methods described herein (see Methods H, I, J and K).

[0693] The amine of formula (2) is commercially available or can be prepared according to the methods described in the literature (e.g., WO2007 / 141009, WO2013 / 064460, WO2015 / 078800, WO2016 / 066574, US2006 / 0116370, WO2007 / 134799, WO2014 / 177487, WO2011 / 144338, EP0807629).

[0694] Method B

[0695] A compound of formula (I-a-1), wherein m, n, R 2 , R 3 , R 4 , R 5 , R 6 , R 9 and Q are as defined above, and

[0696] T is O,

[0697] R 1 is hydrogen, hydroxy, cyano, C1-C6-alkyl or C1-C6-alkoxy,

[0698] R 7 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy,

[0699] R 8 is hydrogen, halogen or C1-C6-alkyl,

[0700] can be prepared by the following method as shown in Scheme 2, which method comprises reacting a compound of formula (3), wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 are as defined above, and

[0701] X is halogen,

[0702] with a compound of formula (4), wherein Q is as defined above, in the presence of an organic or inorganic base.

[0703] Scheme 2: Method B - Synthesis of the compound of formula (I-a-1)

[0704]

[0705] 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.

[0706] The compound of formula (3) can be prepared by method L described herein.

[0707] 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.

[0708] Method C

[0709] The compound of formula (I-b), wherein m, n, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and Q are as defined above, and

[0710] T is S,

[0711] R 1 is hydrogen, can be prepared by the following method as shown in Scheme 3, the method comprising reacting a compound of formula (I-a-2), wherein m, n, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and Q are as defined above, and

[0712] T is O,

[0713] R 1 is hydrogen,

[0714] with a thio reagent.

[0715] Scheme 3: Method C - Synthesis of thioamides of formula (I-b)

[0716]

[0717] Suitable thio reagents for carrying out Method C 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 polymer-supported sulfide reagents, such as those described in Journal of the Chemical Society, Perkin 1 (2001), 358.

[0718] This method is optionally carried out in the presence of a catalytic amount, stoichiometric amount, or 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).

[0719] The compound of formula (I-a-2) is a subset of the compounds of formula (I-a) and (I-a-1) and can be prepared by one or more of the methods described herein.

[0720] Method D

[0721] The compound of formula (I-a-3), wherein m, n, R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 and Q are as defined above, and

[0722] T is O,

[0723] R 1 is H,

[0724] R 7a is chlorine and can be converted to the corresponding compound of formula (I-a-4) in one or more steps by methods described in the literature as shown in Scheme 4, wherein m, n, R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 and Q are as defined above, and

[0725] R1 is H,

[0726] T is O,

[0727] R 7b is hydrogen, iodine, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 20 )2 or -C(=O)(OR 25 ),

[0728] wherein said R 20 and R 25 are as defined above, and

[0729] wherein said C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are substituted as defined above,

[0730] or is converted into a compound of formula (I-a-5), wherein m, n, R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 and Q are as defined above, and

[0731] T is O,

[0732] R 1 is H,

[0733] R 7c is nitro, formyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-hydroxyalkyl, C1-C6-fluoroalkyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, -C(=NR 21 )R 22, -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2 or -S(=O)(=NR 28 )R 29 ,

[0734] wherein said R 21 , R 22 , R 26 , R 27 , R 28 and R 29 are as defined above, and

[0735] wherein C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-hydroxyalkyl, C1-C6-fluoroalkyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl are substituted as defined above.

[0736] Scheme 4: Method D - Synthesis of Compounds of Formulas (I-a-4) and (I-a-5)

[0737]

[0738] Non-limiting examples of the transformation according to Scheme 4 are provided below.

[0739] wherein R 7a is a chlorine atom, a compound of formula (I-a-3) can be converted to a compound of formula (I-a-4) in the presence of a base or by a transition metal-catalyzed method or by a metal photoredox-catalyzed method as described herein, wherein R 7b is cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 20 )2 or -C(=O)(OR 25 ).

[0740] wherein R 7b is a C2-C6-alkenyl substituted with a C1-C3-alkoxy, a compound of formula (I-a-4) can be converted by the method described in the literature (e.g., J. Org. Chem. 1993, 55, 3114) to wherein R 7cA compound of formula (I-a-5) which is a C1-C6-alkylcarbonyl.

[0741] wherein R 7c A compound of formula (I-a-5) which is a C1-C6-alkylcarbonyl can be further converted by methods described in the literature (e.g., Greene's Protective Groups in organic Synthesis; Peter G.M. Wuts; Wiley; Fifth Edition; 2014; 655, 661, 667) into a compound of formula (I-a-5) wherein R 7c is -C(=NR 21 )-R 22 wherein R 21 is as defined above and R 22 is a C1-C6-alkyl.

[0742] wherein R 7c A compound of formula (I-a-5) which is a C1-C6-alkylcarbonyl can be further converted by conventional functional group interconversion methods (e.g., reduction of a ketone to an alcohol in MeOH in the presence of NaBH4) into a compound of formula (I-a-5) wherein R 7c is a C1-C6-hydroxyalkyl.

[0743] wherein R 7c A compound of formula (I-a-5) which is a C1-C6-hydroxyalkyl can be further converted in the presence of a fluorinating agent into a compound of formula (I-a-5) wherein R 7c is a C1-C6-fluoroalkyl. Non-limiting examples of fluorinating agents include sulfur fluorides such as sulfur tetrafluoride, diethylaminosulfur trifluoride, morpholine sulfur trifluoride, bis(2-methoxyethyl)aminosulfur trifluoride, 2,2-difluoro-1,3-dimethylimidazoline or 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride.

[0744] The compound of formula (I-a-3) can be prepared by one or more methods described herein.

[0745] Method E

[0746] A compound of formula (I-a-6), wherein m, n, R 2 , R 3 , R 4 , R 5 , R 6 , R 9 and Q are as defined above, and

[0747] R 1 is hydrogen,

[0748] T is O,

[0749] R 7 is a halogen,

[0750] R 8 is hydrogen and can be converted into the corresponding compound of formula (I-a-7) in one or more steps by methods described in the literature, where m, n, R 2 、R 3 、R 4 、R 5 、R 6 、R 9 and Q are as defined above, and

[0751] R 1 is H,

[0752] T is O,

[0753] R 7 is a halogen,

[0754] R 8a is hydrogen or C1-C6-alkyl,

[0755] wherein the C1-C6-alkyl is optionally substituted as defined above, or is converted into a compound of formula (I-a-8), where m, n, R 2 、R 3 、R 4 、R 5 、R 6 、R 9 and Q are as defined above, and

[0756] R 1 is H,

[0757] T is O,

[0758] R 7 is a halogen,

[0759] R 8b is cyano, amino, mercapto, hydroxy, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C6-cycloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 3- to 14-membered heterocycloxy, 5- to 14-membered heteroaryloxy, C6-C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclic, -N(R30 ) 2, -SR 31 , -S(=O)R 31 or -S(=O)₂R 31 ,

[0760] wherein R 30 and R 31 are as defined above,

[0761] wherein the C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl, C₃-C₆-cycloalkenyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₂-C₆-alkenyloxy, C₂-C₆-haloalkenyloxy, C₂-C₆-alkynyloxy, C₂-C₆-haloalkynyloxy, C₃-C₈-cycloalkoxy, C₆-C 14 -aryloxy, 3- to 14-membered heterocyclic oxy, 5- to 14-membered heteroaryloxy, C₆-C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclic are optionally substituted as defined above,

[0762] Scheme 5: Method E - Synthesis of Amides of Formula (I-a-7) and Formula (I-a-8)

[0763]

[0764] Non-limiting examples of the transformation according to Scheme 5 are provided below.

[0765] The compound of formula (I-a-6) can be converted into a compound of formula (I-a-7) wherein R 8a is halogen in the presence of a base and an electrophile (such as NCS, NBS, NIS, hexachloroethane, bromine or iodine) by the methods described in the literature (e.g., Org. Lett. 2009, 11, 1837). Suitable bases for carrying out the method can be selected from lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, n-butyllithium, methyllithium, TMPZnCl·LiCl (2,2,6,6-tetramethylpiperidyl zinc chloride lithium chloride complex), TMP₂Zn·2MgCl₂·2LiCl (bis(2,2,6,6-tetramethylpiperidyl)zinc magnesium chloride lithium chloride complex), see, for example, Dissertation Albrecht Metzer 2010, University Munich.

[0766] wherein R 8aCompounds of formula (I-a-7) that are halogens can be converted to compounds of formula (I-a-8) in a manner similar to the methods described in the literature (W02008 / 151211; W02000 / 050401; J. Org. Chem. 2005, 70, 1432-1437) in the presence of a base and optionally in the presence of a transition metal catalyst (such as a metal salt or complex), and if appropriate in the presence of a ligand, where R 8b is cyano, amino, mercapto, hydroxy, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C6-cycloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 3- to 14-membered heterocycloxy, 5- to 14-membered heteroaryloxy, C6-C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclo, -N(R 30 )2 or -SR 31 , where R 30 and R 31 are as defined above and where the C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C6-cycloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 3- to 14-membered heterocycloxy, 5- to 14-membered heteroaryloxy, C6-C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclo are optionally substituted as defined above.

[0767] where R 8b is -SR 31 of formula (I-a-8) can be further converted to one where R 8b is -S(=O)R 31 or -S(=O)2R 31 of formula (I-a-8) by reacting the starting compound of formula (I-a-8) with an oxidizing agent (such as hydrogen peroxide), where R 31 each occurrence is as defined above.

[0768] The compound of formula (I-a-6) can be prepared by one or more methods described herein.

[0769] Method F

[0770] A compound of formula (I-d), wherein m, n, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、Q and T are as defined above, and

[0771] G is G 1 ,

[0772] wherein G 1 is a halogen,

[0773] or a compound of formula (6), wherein m, n, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、Q and T are as defined above, and

[0774] G is G 2 ,

[0775] wherein G 2 is a leaving group selected from methanesulfonyloxy, toluenesulfonyloxy and trifluoromethanesulfonyloxy,

[0776] can be reacted with a compound of formula (7) as shown in Scheme 6, wherein

[0777] W 1 is hydrogen, a halogen, potassium trifluoroborate or a group of formula *-B(OR 44 )2, *-Sn(R 45 )3, *-MgX 1

[0778] and *-ZnX 2 ,

[0779] * is the point of attachment to R 6S ,

[0780] R 44 is hydrogen or C1-C6-alkyl or two R 44 together form a -C(CH3)2-C(CH3)2- bridge,

[0781] R 45 is a C1-C6-alkyl group,

[0782] X 1 is a halogen,

[0783] X 2 is a halogen,

[0784] R 6S is cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclic group,

[0785] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted as defined above,

[0786] to provide a compound of formula (I-e), wherein m, n, R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 6S 、R 7 、R 8 、R 9 、Q and T are as defined above.

[0787] Scheme 6: Method F - Synthesis of Compounds of Formula (I-e)

[0788]

[0789] Method F can be carried out by metal catalysis as described herein.

[0790] Alternatively, Method F can be carried out by metal photoredox catalysis. More specifically, a compound of formula (I-d) (wherein G 1The compound of formula (I-d) can be prepared by one or more methods described herein.

[0791] The compound of formula (I-d) can be prepared by one or more methods described herein.

[0792] The compound of formula (6) can be prepared by well-known methods.

[0793] The compound of formula (7) is commercially available.

[0794] Method G

[0795] The compound of formula (I-f), wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q and T are as defined above, and

[0796] G is G 1 ,

[0797] wherein G 1 is a halogen,

[0798] or a compound of formula 8, wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q and T are as defined above, and

[0799] G is G 2 ,

[0800] wherein G 2 is a leaving group selected from methanesulfonyloxy, toluenesulfonyloxy and trifluoromethanesulfonyloxy,

[0801] can be reacted with a compound of formula 9 as shown in Scheme 7, wherein

[0802] Q S is cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6- a haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, a 3- to 7-membered heterocyclic group or a 5- to 6-membered heteroaryl group,

[0803] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C 6- the haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclic group and 5- to 6-membered heteroaryl group are optionally substituted as defined above,

[0804] W 2 is hydrogen, a halogen, potassium trifluoroborate, or a group of the formula # -B(OR 46 )2, # -Sn(R 47 )3, # -MgX 3 or # -ZnX 4 group,

[0805] # is the point connecting to Q S point,

[0806] R 46 is hydrogen or C1-C6-alkyl or two R 46 together form a -C(CH3)2-C(CH3)2- bridge,

[0807] R 47 is C1-C6-alkyl,

[0808] X 3 is a halogen,

[0809] X 4 is a halogen,

[0810] to provide a compound of formula (I-g), wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q, Q S and T are as defined above.

[0811] Scheme 7: Method G - Synthesis of the compound of formula (I-g)

[0812]

[0813] Method G can be carried out by transition metal catalysis.

[0814] Alternatively, Method G can be carried out by metal photoredox catalysis. More specifically, the compound of formula (I-f) (wherein G 1 is preferably Br or I) can be converted into the compound of formula (I-g) by a method of metal photoredox catalysis in the presence of a photosensitizer (such as Ir and Ru complexes) or an organic dye and a metal catalyst (such as Ni complex). This reaction can be carried out in the presence of a ligand and, if appropriate, in the presence of a base under blue light or white light irradiation.

[0815] The compound of formula (I-f) can be prepared by one or more methods described herein.

[0816] The compound of formula (8) can be prepared by well-known methods.

[0817] The compound of formula (9) is commercially available.

[0818] Process for preparing the compound of formula (1)

[0819] The compound of formula (1) can be obtained directly by carrying out Method H described below, or can be obtained by converting or derivatizing another compound of formula (1) prepared according to the methods described herein. The compounds of formula (1-a)-(1-h) are various subsets of formula (1).

[0820] Method H

[0821] The compound of formula (1-a), wherein R 9 and Q are as defined above, and

[0822] R 7 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy,

[0823] R 8 is hydrogen, halogen or C1-C6-alkyl,

[0824] U 1 is hydroxy or C1-C6-alkoxy,

[0825] can be prepared as shown in Scheme 8 in the presence of a base and in the presence of a suitable transition metal catalyst salt or complex, and if appropriate in the presence of a ligand by the following method. First, the compound of formula (10), wherein R 7 、R 8 and R 9 are as defined above, and

[0826] X 5 is a halogen,

[0827] is treated with a base (such as nBuLi or LDA) and carbon dioxide or a reagent of formula (11), where

[0828] E is a halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy,

[0829] U 2 is C1-C6-alkoxy,

[0830] to give a compound of formula (12), where X 5 , R 7 , R 8 and R 9 are as defined above, and

[0831] U 1 is hydroxy or C1-C6-alkoxy,

[0832] which is then reacted with a compound of formula (4), where Q is as defined above.

[0833] Scheme 8: Method H - Synthesis of compounds of formula (1-a)

[0834]

[0835] Compounds of formula (10) and formula (11) are commercially available.

[0836] Compounds of formula (4) are commercially available or can be obtained by conversion or derivatization of another compound of formula (4) according to well-known methods.

[0837] Method I

[0838] A compound of formula (1-b), where R 8 , R 9 and Q are as defined above, and

[0839] U 1 is C1-C6-alkoxy,

[0840] R 7a is hydrogen or chlorine,

[0841] can be converted to the corresponding compound of formula (1-c) in one or more steps by known methods as shown in Scheme 9, where U 1 , R 8 , R 9 and Q are as defined above, and

[0842] R 7bis hydrogen, iodine, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 20 )2 or -C(=O)(OR 25 ),

[0843] wherein C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C8-cycloalkylthio, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, -N(R 20 )2 and -C(=O)(OR 25 ) are as defined above and are optionally substituted as defined above,

[0844] or is converted to a compound of formula (1-d), wherein U 1 , R 8 , R 9 and Q are as defined above, and

[0845] R 7c is nitro, formyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-hydroxyalkyl, C1-C6-fluoroalkyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, -C(=NR 21 )R 22 , -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2 or -S(=O)2N(R 28 )R 29 ,

[0846] wherein C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-hydroxyalkyl, C1-C6-fluoroalkyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, -C(=NR 21 )R 22 、-C(=O)N(R 26 )2、-S(=O)2N(R 27 )2 and -S(=O)2N(R 28 )R 29 as defined above and optionally substituted as defined above.

[0847] Scheme 9: Process I - Synthesis of Compounds of Formula (1-c) and Formula (1-d)

[0848]

[0849] Non-limiting examples of the transformation can be carried out according to the description provided in Process D.

[0850] The compounds of formula (1-b) can be prepared by one or more of the methods described herein.

[0851] Process J

[0852] A compound of formula (1-e), wherein R 7 、R 9 and Q are as defined above, and

[0853] U 1 is C1-C6-alkoxy,

[0854] can be converted in one or more steps to the corresponding compound of formula (1-f) as shown in Scheme 10 by methods described in the literature, wherein U 1 、R 7 、R 9 and Q are as defined above, and

[0855] R 8a is halogen, preferably fluorine and iodine, or C1-C6-alkyl,

[0856] or a compound of formula (1-g), wherein U 1 、R 7 、R 9 and Q are as defined above, and

[0857] R 8bis cyano, amino, mercapto, hydroxy, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C6-cycloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 3- to 14-membered heterocycloxy, 5- to 14-membered heteroaryloxy, C6-C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclo, -N(R 30 )2, -SR 31 , -S(=O)R 31 or -S(=O)2R 31 ,

[0858] wherein C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C3-C6-cycloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 3- to 14-membered heterocycloxy, 5- to 14-membered heteroaryloxy, C6-C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclo, -N(R 30 )2, -SR 31 , -S(=O)R 31 or -S(=O)2R 31 are as defined above and are optionally substituted as defined above.

[0859] Scheme 10: Process J - Synthesis of Compounds of Formulas (1-f) and (1-g)

[0860]

[0861] Non-limiting examples of the transformation can be carried out according to the description provided in Process E.

[0862] The compounds of formula (1-e) can be prepared by one or more of the methods described herein.

[0863] Process K

[0864] A compound of formula (1-h), wherein Q is as defined above, and

[0865] U 1 is a C1-C6-alkoxy group,

[0866] R 7 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy,

[0867] R 8 is hydrogen, halogen or C1-C6-alkyl,

[0868] R 9 is halogen,

[0869] can be prepared by the following method as shown in Scheme 11: reacting a compound of formula (15), wherein R 7 、R 8 、R 9 and Q are as defined above, with carbon dioxide or a reagent of formula (11), wherein

[0870] U 2 is a C1-C6-alkoxy group,

[0871] E is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy.

[0872] Scheme 11: Method K - Synthesis of Compounds of Formula (1-h)

[0873]

[0874] The compound of formula (15) can be prepared by a method analogous to that described in the literature (W02009 / 044160; W02016 / 040222) in the presence of a base and in the presence of a suitable transition metal catalyst salt or complex, and if appropriate in the presence of a ligand, by reacting a compound of formula (13), wherein R 7 、R 8 and R 9 are as defined above, with a reagent of formula (4), wherein Q is as defined above, and

[0875] G 3 is a group of formula # -B(OR 46 )2,

[0876] wherein

[0877] # is the point of attachment to Q,

[0878] R 46 is hydrogen or C1-C6-alkyl or two R 46Together form a -C(CH3)2-C(CH3)2- bridge.

[0879] The starting materials of formulas (11), (13), and (14) are commercially available.

[0880] Process for preparing the compound of formula (3)

[0881] Method L

[0882] A compound of formula (3), wherein m, n, R 2 , R 3 , R 4 , R 5 , R 6 and R 9 are as defined above, and

[0883] X is a halogen,

[0884] R 1 is hydrogen, hydroxy, cyano, C1-C6-alkyl or C1-C6-alkoxy,

[0885] R 7 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy,

[0886] R 8 is hydrogen, halogen or C1-C6-alkyl,

[0887] can be prepared by a method comprising reacting a compound of formula (12), wherein X, R 7 , R 8 and R 9 are as defined above, and

[0888] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[0889] with an amine of formula (2), wherein m, n, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined above.

[0890] Scheme 12: Method L - Synthesis of the compound of formula (3)

[0891]

[0892] Method L can be carried out using the same conditions as described in Method A.

[0893] wherein U1 Compounds of formulas (1-a), (1-b), (1-c), (1-d), (1-e), (1-f), (1-g) and (1-h) that are C1-C6-alkoxy can be converted, by well-known functional group interconversion methods (e.g., by hydrolyzing an ester group with LiOH in THF / water), into those in which U 1 is a hydroxyl group, of formulas (1-a), (1-b), (1-c), (1-d), (1-e), (1-f), (1-g) and (1-h).

[0894] wherein U 1 is a hydroxyl group, of formulas (1-a), (1-b), (1-c), (1-d), (1-e), (1-f), (1-g) and (1-h), can be converted, by well-known methods, in the presence of a halogenating agent, into those in which U 1 is a halogen, of formulas (1-a), (1-b), (1-c), (1-d), (1-e), (1-f), (1-g) and (1-h). Suitable halogenating reagents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride or thionyl chloride.

[0895] Examples of such conversions are described below.

[0896] The compounds of the present invention can be prepared according to the above methods. However, it should be understood that, based on his common knowledge and 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 present invention to be synthesized as desired.

[0897] Intermediate for preparing the compound of formula (I)

[0898] The present invention also relates to intermediates for the preparation of the compounds of formula (I).

[0899] Accordingly, the present invention relates to compounds of formula (1):

[0900]

[0901] wherein

[0902] Q is phenyl, azulenyl, naphthyl, C7-C 12 -carbocyclic ring, 6- to 14-membered heterocyclic group or 5- to 14-membered heteroaryl group,

[0903] wherein the phenyl group is substituted with one to five substituents Q S substituted,

[0904] wherein the azulenyl, naphthyl, C7-C 12 -carbocyclic ring, 6- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl group are optionally substituted with one to five substituents Q S substituted,

[0905] wherein Q S is independently selected from 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 33 , -NR 34 C(=O)R 35 , -C(=O)N(R 36 )2, -C(=S)R 37 , -C(=S)N(R 38 )2, -C(=NR 39 )R 40 and -C(=NOR 41 )R 42 and -N(R 43 )2,

[0906] wherein

[0907] 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-C 6-A haloalkenyl group, a C2-C6-alkynyl group, a C2-C6-haloalkynyl group, a C2-C6-alkenyloxy group, a C2-C6-haloalkenyloxy group, a C1-C6-alkylthio group, a C1-C6-haloalkylthio group, a C1-C6-alkylsulfinyl group, a C1-C6-haloalkylsulfinyl group, a C1-C6-alkylsulfonyl group, a C1-C6-haloalkylsulfonyl group, -O-Si(C1-C6-alkyl)3 and -Si(C1-C6-alkyl)3 are each optionally substituted by one to three 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 a 3- to 7-membered heterocyclic group,

[0908] The C3-C8-cycloalkyl group, C3-C8-cycloalkoxy group, C3-C6-cycloalkenyl group, 3- to 7-membered heterocyclic group and 5- to 14-membered heteroaryl group are each optionally substituted by one to three 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 a 3- to 7-membered heterocyclic group,

[0909] wherein the C3-C8-cycloalkyl group, C3-C8-halocycloalkyl group and non-aromatic 3- to 7-membered heterocyclic group are also optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl group,

[0910] R 34 、R 35 、R 36 、R 37 、R 38 、R 39 、R 40 、R 41 and R 42 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0911] wherein

[0912] The C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy group is optionally further substituted by one to three 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,

[0913] R 43 is hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl or C3-C8-cycloalkyl,

[0914] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl and C2-C6-haloalkenyl are optionally further substituted by one to three 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,

[0915] wherein the C3-C8-cycloalkyl is further optionally substituted by one to three 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 R Qs substituents,

[0916] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic groups are further optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0917] R 7is halogen, cyano, isocyano, hydroxy, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, 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-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclic oxy group, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 20 )2, -C(=NR 21 )R 22 , -NR 23 C(=O)R 24 , -C(=O)(OR 25 ), -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2 or -S(=O)(=NR 28 )R 29 ,

[0918] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents,

[0919] wherein C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocycloalkyloxy are optionally substituted with one to three R 7Sc substituents,

[0920] R 20 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C 14 -carbocycle, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclic group,

[0921] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are optionally substituted with one to three substituents R 7Sa substituted,

[0922] and

[0923] wherein C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted with one to three substituents R 7Sc substituted,

[0924] R 21 and R 22 are independently hydroxy, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino,

[0925] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino are optionally substituted with one to three R 7Sa substituents,

[0926] R 23 、R 24 、R 25 、R 26 、R 27 、R 28 and R 29Independently is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl,

[0927] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted by one to three R 7Sa substituents,

[0928] and

[0929] wherein the C3-C8-cycloalkyl is optionally substituted by one to three R 7Sc substituents,

[0930] wherein

[0931] R 7Sa independently is cyano, hydroxy, carboxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C6-C 14 -aryl or a 3- to 7-membered heterocyclic group,

[0932] R 7Sc independently is halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 or a 3- to 7-membered heterocyclic group,

[0933] or

[0934] two R 7Sc substituents bonded to the same carbon atom, C1-C6-alkyl, together form a C3-C8-cycloalkyl,

[0935] R 8 and R 9 are as defined above,

[0936] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[0937] provided that the compound of formula (1) is not:

[0938] 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinic acid

[0939] 2267344-96-5

[0940] 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinic acid chloride

[0941] 2267344-97-6

[0942] Ethyl 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinate

[0943] 2267344-95-4

[0944] 5-[2-Methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid

[0945] 2267344-69-2

[0946] 3-Fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid 2267343-60-0

[0947] 3-Fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid chloride 2267343-61-1

[0948] Ethyl 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinate 2267343-59-7

[0949] 3-Fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid

[0950] 2267342-98-1

[0951] Ethyl 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinate

[0952] 2267342-97-0

[0953] Methyl 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinate

[0954] 2-Nitro-5-(pyridin-3-yloxy)isonicotinic acid 1984094-45-2

[0955] 2-Chloro-5-(4-methoxyphenoxy)isonicotinic acid 1215868-10-2

[0956] 2-Methyl-5-(4-nitrophenoxy)isonicotinic acid 52736-42-2

[0957] Ethyl 2-methyl-5-(4-nitrophenoxy)isonicotinate 52685-78-6

[0958] 3-Methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylic acid

[0959] 2267345-11-7

[0960] Methyl 3-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylate

[0961] 2267345-12-8

[0962] 3-Methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carbonyl chloride

[0963] 2267345-13-9

[0964] 3-Fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylic acid 2267344-46-5

[0965] 3-Fluoro-5-[2-methyl-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)pyridine-4-carboxylic acid

[0966] 2597220-53-4

[0967] 5-[2-Chloro-4-(trifluoromethoxy)phenoxy]-3-fluoro-2-(trifluoromethyl)pyridine-4-carboxylic acid

[0968] 2600737-76-4

[0969] 5-[2-Methoxy-4-(trifluoromethoxy)phenoxy]-3-methyl-2-(trifluoromethyl)pyridine-4-carboxylic acid

[0970] 2451904-00-8

[0971] 5-(3,4-Difluoro-2-methoxyphenoxy)-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylic acid

[0972] 2451904-62-2

[0973] Ethyl 5-(3,4-difluoro-2-methoxyphenoxy)-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylate

[0974] 3-Fluoro-5-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451905-95-4

[0975] 5-[3-Fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-methyl-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451906-03-7

[0976] 5-[3-Fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451905-97-6

[0977] Accordingly, the present invention relates to compounds of formula (1):

[0978]

[0979] wherein

[0980] Q is C6-C 14 -aryl, C7-C 12 -carbocycle, a 6- to 14-membered heterocyclic group or a 5- to 14-membered heteroaryl group,

[0981] wherein the C6-C 14 -aryl, C7-C 12 -carbocycle, 6- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl group are optionally substituted by one to five Q S substituents, and the Q S substituents are independently selected from 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-C 6- 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 33 , -NR 34 C(=O)R 35 , -C(=O)N(R 36 )2, -C(=S)R 37 , -C(=S)N(R 38)2, -C(=NR 39 )R 40 and -C(=NOR 41 )R 42 and -N(R 43 )2,

[0982] wherein

[0983] 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-C 6- 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 further substituted by one to three 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,

[0984] the C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclic groups and 5- to 14-membered heteroaryl groups are optionally further substituted by one to three 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,

[0985] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and non-aromatic 3- to 7-membered heterocyclic groups are further optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0986] R 34 、R 35 、R 36 、R 37 、R38 , R 39 , R 40 , R 41 and R 42 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy,

[0987] wherein

[0988] the C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy is optionally further substituted by one to three 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,

[0989] R 43 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 further substituted by one to three 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,

[0990] wherein the C3-C8-cycloalkyl is further optionally substituted by one to three 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 R Qs substituents,

[0991] wherein the C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic group are further optionally substituted by two substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[0992] R 7is halogen, cyano, isocyano, hydroxy, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, 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-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclic oxy group, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 20 )2, -C(=NR 21 )R 22 , -NR 23 C(=O)R 24 , -C(=O)(OR 25 ), -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2 or -S(=O)(=NR 28 )R 29 ,

[0993] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents,

[0994] Among them, C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocycloaryloxy are optionally substituted by one to three R 7Sc substituents,

[0995] R 20 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C 14 -carbocycle, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclic group,

[0996] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are optionally substituted by one to three substituents R 7Sa substituted,

[0997] and

[0998] wherein C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted by one to three substituents R 7Sc substituted,

[0999] R 21 and R 22 are independently hydroxyl, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino,

[1000] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino are optionally substituted by one to three R 7Sa substituents,

[1001] R 23 、R 24 、R 25 、R 26 、R 27 、R 28 and R 29Independently is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl,

[1002] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted by one to three R 7Sa substituents,

[1003] and

[1004] wherein the C3-C8-cycloalkyl is optionally substituted by one to three R 7Sc substituents,

[1005] wherein

[1006] R 7Sa is independently cyano, hydroxy, carboxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C6-C 14 -aryl or a 3- to 7-membered heterocyclic group,

[1007] R 7Sc is independently halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 or a 3- to 7-membered heterocyclic group,

[1008] or

[1009] two R 7Sc substituents C1-C6-alkyl bonded to the same carbon atom together form a C3-C8-cycloalkyl,

[1010] R 8 and R 9 are as defined above,

[1011] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[1012] provided that the compound of formula (1) is not:

[1013] 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinic acid

[1014] 2267344-96-5

[1015] 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinic acid chloride

[1016] 2267344-97-6

[1017] Ethyl 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinate

[1018] 2267344-95-4

[1019] 5-[2-Methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid

[1020] 2267344-69-2

[1021] 3-Fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid 2267343-60-0

[1022] 3-Fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid chloride 2267343-61-1

[1023] Ethyl 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinate 2267343-59-7

[1024] 3-Fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid

[1025] 2267342-98-1

[1026] Ethyl 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinate

[1027] 2267342-97-0

[1028] Methyl 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinate

[1029] 2-Nitro-5-(pyridin-3-yloxy)isonicotinic acid 1984094-45-2

[1030] 2-Chloro-5-(4-methoxyphenoxy)isonicotinic acid 1215868-10-2

[1031] 2-Methyl-5-(4-nitrophenoxy)isonicotinic acid 52736-42-2

[1032] Ethyl 2-methyl-5-(4-nitrophenoxy)isonicotinate 52685-78-6

[1033] 3-Methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylic acid

[1034] 2267345-11-7

[1035] Methyl 3-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylate

[1036] 2267345-12-8

[1037] 3-Methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carbonyl chloride

[1038] 2267345-13-9

[1039] 3-Fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylic acid 2267344-46-5

[1040] 3-Fluoro-5-[2-methyl-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)pyridine-4-carboxylic acid

[1041] 2597220-53-4

[1042] 5-[2-Chloro-4-(trifluoromethoxy)phenoxy]-3-fluoro-2-(trifluoromethyl)pyridine-4-carboxylic acid

[1043] 2600737-76-4

[1044] 5-[2-Methoxy-4-(trifluoromethoxy)phenoxy]-3-methyl-2-(trifluoromethyl)pyridine-4-carboxylic acid

[1045] 2451904-00-8

[1046] 5-(3,4-Difluoro-2-methoxyphenoxy)-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylic acid

[1047] 2451904-62-2

[1048] Ethyl 5-(3,4-difluoro-2-methoxyphenoxy)-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylate

[1049] 3-Fluoro-5-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451905-95-4

[1050] 5-[3-Fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-methyl-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451906-03-7

[1051] 5-[3-Fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451905-97-6

[1052] Accordingly, the present invention also preferably relates to a compound of formula (1):

[1053]

[1054] wherein

[1055] Q is phenyl, 2,3-dihydrobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, 2,3-dihydro-1,4-benzodioxenyl, 5,6,7,8-tetrahydroquinolinyl, 2,3-dihydrobenzofuranyl, thienyl, pyridyl or indolyl,

[1056] wherein the phenyl is substituted with one to three substituents Q S substituted,

[1057] and wherein 2,3-dihydrobenzofuranyl, dihydroindolyl, 1,3-benzodioxolyl, chromanyl, 2,3-dihydro-1,4-benzodioxenyl, 5,6,7,8-tetrahydroquinolinyl, 2,3-dihydrobenzofuranyl, thienyl, pyridyl, indolyl are optionally substituted with one to three substituents Q S substituted,

[1058] wherein

[1059] Q S is independently selected from halogen, cyano, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkynyl, C3-C6-cycloalkyl, oxetanyl and -N(R 43 )2,

[1060] wherein

[1061] the C3-C6-cycloalkyl and oxetanyl are optionally further substituted with one or two substituents independently selected from halogen and C1-C4-alkyl,

[1062] R 43 is independently hydrogen or C1-C4-alkyl,

[1063] R 7is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, -N(R 20 )2, -C(=NR 21 )R 22 or -C(=O)(OR 25 ),

[1064] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents,

[1065] wherein the C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl are optionally substituted by one or two R 7Sc substituents,

[1066] wherein

[1067] R 20 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl,

[1068] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[1069] R 22 is C1-C4-alkyl,

[1070] R 25 is hydrogen or C1-C4-alkyl,

[1071] and wherein

[1072] R 7Sa is independently C1-C4-alkoxy or phenyl,

[1073] R 7Sc is independently halogen or C1-C4-alkyl,

[1074] R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridyl or -N(R 30 )2,

[1075] wherein the C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl and pyridinyl are each optionally substituted by one or two R 8Sc substituents,

[1076] R 30 is C1-C6-alkyl,

[1077] R 8Sc independently is halogen or C1-C4-alkyl,

[1078] R 9 is hydrogen or halogen,

[1079] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[1080] with the proviso that the compound of formula (1) is not:

[1081] 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinic acid

[1082] 2267344-96-5

[1083] 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinic acid chloride

[1084] 2267344-97-6

[1085] 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]isonicotinic acid ethyl ester

[1086] 2267344-95-4

[1087] 5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid

[1088] 2267344-69-2

[1089] 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid 2267343-60-0

[1090] 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid chloride 2267343-61-1

[1091] 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid ethyl ester 2267343-59-7

[1092] 3-Fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinic acid

[1093] 2267342-98-1

[1094] Ethyl 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinate

[1095] 2267342-97-0

[1096] Methyl 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)isonicotinate

[1097] 2-Nitro-5-(pyridin-3-yloxy)isonicotinic acid 1984094-45-2

[1098] 2-Chloro-5-(4-methoxyphenoxy)isonicotinic acid 1215868-10-2

[1099] 2-Methyl-5-(4-nitrophenoxy)isonicotinic acid 52736-42-2

[1100] Ethyl 2-methyl-5-(4-nitrophenoxy)isonicotinate 52685-78-6

[1101] 3-Methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylic acid

[1102] 2267345-11-7

[1103] Methyl 3-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylate

[1104] 2267345-12-8

[1105] 3-Methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carbonyl chloride

[1106] 2267345-13-9

[1107] 3-Fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]pyridine-4-carboxylic acid 2267344-46-5

[1108] 3-Fluoro-5-[2-methyl-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)pyridine-4-carboxylic acid

[1109] 2597220-53-4

[1110] 5-[2-Chloro-4-(trifluoromethoxy)phenoxy]-3-fluoro-2-(trifluoromethyl)pyridine-4-carboxylic acid

[1111] 2600737-76-4

[1112] 5-[2-Methoxy-4-(trifluoromethoxy)phenoxy]-3-methyl-2-(trifluoromethyl)pyridine-4-carboxylic acid

[1113] 2451904-00-8

[1114] 5-(3,4-Difluoro-2-methoxyphenoxy)-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylic acid

[1115] 2451904-62-2

[1116] Ethyl 5-(3,4-difluoro-2-methoxyphenoxy)-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylate

[1117] 3-Fluoro-5-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451905-95-4

[1118] 5-[3-Fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-methyl-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451906-03-7

[1119] 5-[3-Fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]-3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylic acid 2451905-97-6

[1120] Therefore, the present invention more preferably relates to a compound of formula (1)

[1121]

[1122] wherein

[1123] Q is naphthyl, indanyl, 1,3-benzodioxolyl, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl, thienyl, pyridyl, quinolinyl or a group of the following formula

[1124]

[1125] wherein

[1126] § 2 is the point of attachment to the oxygen atom

[1127] Q S1 is hydrogen or a halogen,

[1128] Q S2 is hydrogen, a halogen, a cyano group, a nitro group, a C1-C4-alkyl group, a trifluoromethyl group, a difluoromethyl group, a C1-C4-alkylcarbonyl group, a C1-C6-alkoxy group, a difluoromethoxy group, a trifluoromethoxy group, a C2-C4-alkynyl group, a C3-C6-cycloalkyl group, an oxiranyl group or an oxetanyl group,

[1129] with the proviso that Q S1 and Q S2 are each independently of the other different from hydrogen.

[1130] and

[1131] wherein the naphthyl group, indanyl group, 1,3-benzodioxolyl group, 4a,5,6,7-tetrahydropyrrolo[1,2-b]pyridazinyl group, thienyl group, pyridyl group and quinolinyl group are each optionally substituted by one to three substituents Q S substituted,

[1132] wherein

[1133] Q S is independently selected from a halogen, a cyano group, a nitro group, a formyl group, a C1-C4-alkyl group, a C1-C4-haloalkyl group, a C1-C4-alkylcarbonyl group, a C1-C4-alkoxy group, a C1-C4-haloalkoxy group, a C1-C4-alkoxycarbonyl group, a C2-C4-alkenyl group, a C2-C4-alkynyl group, a C1-C4-alkylthio group, a C3-C6-cycloalkyl group, an oxetanyl group, a phenyl group, a pyrazolyl group, a pyridyl group and -N(R 43 )2,

[1134] wherein

[1135] the C1-C4-alkyl group and the C1-C4-alkoxy group are each optionally substituted by one or two substituents independently selected from a hydroxyl group, a C1-C4-alkoxy group and a C1-C4-alkoxycarbonyl group,

[1136] the C3-C6-cycloalkyl group, the phenyl group, the pyrazolyl group and the pyridyl group are each optionally substituted by one or two substituents independently selected from a halogen and a C1-C4-alkyl group,

[1137] and wherein

[1138] R 43 is independently hydrogen or a C1-C4-alkyl group,

[1139] R 7is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, -N(R 20 )2, -C(=NR 21 )R 22 or -C(=O)(OR 25 ),

[1140] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents,

[1141] wherein the C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl and piperidinyl are optionally substituted by one or two R 7Sc substituents,

[1142] wherein

[1143] R 20 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl,

[1144] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[1145] R 22 is C1-C4-alkyl,

[1146] R 25 is hydrogen or C1-C4-alkyl,

[1147] and wherein

[1148] R 7Sa is independently C1-C4-alkoxy or phenyl,

[1149] R 7Sc is independently halogen or C1-C4-alkyl,

[1150] R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridyl or -N(R 30 )2,

[1151] wherein the C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl and pyridinyl are optionally substituted by one or two R 8Sc substituents,

[1152] R 30 is C1-C6-alkyl,

[1153] R 8Sc independently are halogen or C1-C4-alkyl,

[1154] R 9 is hydrogen or halogen,

[1155] U 1 is hydroxy, halogen or C1-C6-alkoxy.

[1156] The present invention also relates to a compound of formula (3)

[1157]

[1158] wherein

[1159] n is 1,

[1160] m is 1,

[1161] R 1 is hydrogen,

[1162] R 2 and R 3 are hydrogen,

[1163] R 4 and R 5 independently are hydrogen or fluorine, provided that at least one of R 4 and R 5 is not hydrogen,

[1164] R 6 is C7-C 12 -carbocycle, C6-C 14 -aryl, 3- to 14-membered heterocyclic group or 5- to 14-membered heteroaryl,

[1165] wherein the C7-C 12 -carbocycle, C6-C 14 -aryl, 3- to 14-membered heterocyclic group and 5- to 14-membered heteroaryl are optionally substituted by one to four R 6S substituents,

[1166] wherein

[1167] R 6SIndependently 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, 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,

[1168] 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 one to three 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,

[1169] and

[1170] 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 also optionally substituted with one to four substituents independently selected from 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,

[1171] or

[1172] two C1-C6-alkyl substituents attached to the same carbon atom form a C3-C8-cycloalkyl ring,

[1173] or

[1174] two R 6S substituents optionally together with the carbon atom to which they are attached form a C3-C8-cycloalkyl ring,

[1175] and wherein

[1176] R 15 is hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl,

[1177] wherein said C1-C6-alkyl is also optionally substituted with one to three 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,

[1178] and

[1179] wherein said C3-C8-cycloalkyl is also optionally substituted with one to four substituents independently selected from 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,

[1180] R 16 , R 17 , R 18 and R 19 are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl,

[1181] wherein the C1-C6-alkyl or C1-C6-haloalkyl is also optionally substituted by one to three 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,

[1182] R 7 is halogen, cyano, isocyano, hydroxy, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, 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-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclic group oxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 20 )2, -C(=NR 21 )R 22 , -NR 23 C(=O)R 24 , -C(=O)(OR 25 ),

[1183] , -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2 or -S(=O)(=NR 28 )R 29, where C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents,

[1184] where C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocyclic oxy group are optionally substituted by one to three R 7Sc substituents,

[1185] R 20 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C 14 -carbocyclic ring, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclic group,

[1186] where C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are optionally substituted by one to three substituents R 7Sa substituted,

[1187] and

[1188] where C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted by one to three substituents R 7Sc substituted,

[1189] R 21 and R 22independently is hydroxy, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino,

[1190] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino is optionally substituted by one to three R 7Sa substituents,

[1191] R 23 、R 24 、R 25 、R 26 、R 27 、R 28 and R 29 independently is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl,

[1192] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted by one to three R 7Sa substituents,

[1193] and

[1194] wherein the C3-C8-cycloalkyl is optionally substituted by one to three R 7Sc substituents,

[1195] wherein

[1196] R 7Sa independently is cyano, hydroxy, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C6-C 14 -aryl or a 3- to 7-membered heterocyclic group,

[1197] R 7Sc independently is halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 or a 3- to 7-membered heterocyclic group,

[1198] or

[1199] two R 7Sc substituents C1-C6-alkyl bonded to the same carbon atom together form a C3-C8-cycloalkyl,

[1200] R 8 is hydrogen, a halogen or a C1-C6-alkyl group,

[1201] R 9 is hydrogen, a halogen, a cyano group or a C1-C4-alkyl group,

[1202] X is a halogen,

[1203] provided that the compound of formula (3) is not:

[1204] 5-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-2-(trifluoromethyl)isonicotinamide

[1205] 1918165-74-8

[1206] 3-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide 1918165-35-1

[1207] 3-bromo-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide 1918165-33-9

[1208] The present invention also relates to a compound of formula (3)

[1209]

[1210] wherein

[1211] n is 1,

[1212] m is 1,

[1213] R 1 is hydrogen,

[1214] R 2 and R 3 are hydrogen,

[1215] R 4 and R 5 are independently hydrogen or fluorine, provided that at least one of R 4 and R 5 is not hydrogen,

[1216] R 6 is a C7-C 12 -carbocycle, a C6-C 14 -aryl, a 5- to 14-membered heteroaryl and a 6- to 14-membered heterocyclic group,

[1217] wherein the C7-C 12 -carbocycle, the C6-C 14-Aryl, 6- to 14-membered heterocyclic group, and 5- to 14-membered heteroaryl are optionally substituted with one to four R 6S substituents,

[1218] wherein

[1219] R 6S is independently 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, 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,

[1220] 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 with one to three 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,

[1221] and

[1222] 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 also optionally substituted by one to four 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,

[1223] or

[1224] two substituents C1-C6-alkyl attached to the same carbon atom form a C3-C8-cycloalkyl,

[1225] or

[1226] two R 6S substituents optionally together with the carbon atom to which they are attached form a C3-C8-cycloalkyl,

[1227] R 15 is hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[1228] wherein the C1-C6-alkyl is also optionally substituted by one to three 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,

[1229] and

[1230] wherein the C3-C8-cycloalkyl is also optionally substituted by one to four 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,

[1231] R 16 、R 17 、R 18 and R 19 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl,

[1232] wherein the C1-C6-alkyl or C1-C6-haloalkyl substituent is also optionally substituted by one to three 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 non-aromatic 3- to 7-membered heterocyclic groups,

[1233] R 7 is halogen, cyano, isocyano, hydroxy, mercapto, nitro, amino, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, 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-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclic oxy group, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 20 )2, -C(=NR 21 )R 22 , -NR 23 C(=O)R 24 , -C(=O)(OR 25 ), -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2 or -S(=O)(=NR 28 )R 29 ,

[1234] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by one to three R 7Sa substituents,

[1235] wherein C3-C8-cycloalkylthio, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclic group, C3-C8-cycloalkoxy, C6-C 14 -aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocycloxy are optionally substituted by one to three R 7Sc substituents,

[1236] R 20 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, aromatic C6-C 14 -carbocycle, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclic group,

[1237] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl are optionally substituted by one to three substituents R 7Sa substituted,

[1238] and

[1239] wherein C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclic group are optionally substituted by one to three substituents R 7Sc substituted,

[1240] R 21 and R 22independently is hydroxy, amino, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino,

[1241] wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino or di-(C1-C6-alkyl)amino is optionally substituted by one to three R 7Sa substituents,

[1242] R 23 、R 24 、R 25 、R 26 、R 27 、R 28 and R 29 independently is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl and C3-C8-cycloalkyl,

[1243] wherein the C1-C6-alkyl and C1-C6-haloalkyl are optionally substituted by one to three R 7Sa substituents,

[1244] and

[1245] wherein the C3-C8-cycloalkyl is optionally substituted by one to three R 7Sc substituents,

[1246] wherein

[1247] R 7Sa independently is cyano, hydroxy, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C6-C 14 -aryl or a 3- to 7-membered heterocyclic group,

[1248] R 7Sc independently is halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 or a 3- to 7-membered heterocyclic group,

[1249] or

[1250] two R 7Sc substituents C1-C6-alkyl bonded to the same carbon atom together form a C3-C8-cycloalkyl,

[1251] R 8 is hydrogen, a halogen or a C1-C6-alkyl group,

[1252] R 9 as defined above,

[1253] X is a halogen,

[1254] with the proviso that the compound of formula (3) is not:

[1255] 5-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-2-(trifluoromethyl)isonicotinamide

[1256] 1918165-74-8

[1257] 3-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide 1918165-35-1

[1258] 3-bromo-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide 1918165-33-9

[1259] The present invention also preferably relates to a compound of formula (3)

[1260]

[1261] wherein

[1262] n is 1,

[1263] m is 1,

[1264] R 1 is hydrogen,

[1265] R 2 and R 3 are hydrogen,

[1266] R 4 and R 5 are independently hydrogen or fluorine,

[1267] with the proviso that at least one of R 4 and R 5 is not hydrogen,

[1268] R 6 is phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, phenoxy or benzyloxy,

[1269] wherein the phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl, indolyl, phenoxy or benzyloxy is optionally substituted by one to three R 6S substituents,

[1270] wherein

[1271] R 6S is independently 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 or -C(=O)(OR 17 ),

[1272] wherein the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl and pyridyl are further optionally substituted by one or two substituents independently selected from fluorine, chlorine, C1-C4-alkyl and C1-C4-haloalkyl,

[1273] and wherein

[1274] R 16 is C1-C4-alkyl,

[1275] R 17 is hydrogen or C1-C4-alkyl,

[1276] R 7 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, -N(R 20 )2, -C(=NR 21 )R 22 or -C(=O)(OR 25 ),

[1277] wherein the C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa substituents,

[1278] wherein the C3-C6-cycloalkyl, pyridyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl are optionally substituted by one or two R 7Sc substituents,

[1279] wherein

[1280] R 20 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl,

[1281] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[1282] R 22 is C1-C4-alkyl,

[1283] R 25 is hydrogen or C1-C4-alkyl,

[1284] and wherein

[1285] R 7Sa is independently C1-C4-alkoxy or phenyl,

[1286] R 7Sc is independently halogen or C1-C4-alkyl,

[1287] R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridyl or -N(R 30 )2,

[1288] wherein the C3-C6-cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl and pyridyl are optionally substituted by one or two R 8Sc substituents,

[1289] R 30 is C1-C6-alkyl,

[1290] R 8Sc is independently halogen or C1-C4-alkyl,

[1291] R 9 is hydrogen or halogen,

[1292] X is halogen,

[1293] provided that the compound of formula (3) is not:

[1294] 5-Chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-2-(trifluoromethyl)isonicotinamide

[1295] 1918165-74-8

[1296] 3-Chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide 1918165-35-1

[1297] 3-Bromo-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide 1918165-33-9

[1298] The present invention also relates to an intermediate of formula (4)

[1299] Q-OH (4),

[1300] wherein

[1301] Q is a group of the following formula

[1302]

[1303] wherein

[1304] *** is the point of attachment to the hydroxyl group,

[1305] A is C or N,

[1306] Q S is C3-C4-cycloalkyl, C3-C8-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl or C2-C6-alkynyl,

[1307] provided that the compound of formula (4) does not represent:

[1308] 2-Fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)phenol 2168012-00-6

[1309] 3-(1-Ethoxyvinyl)-2-fluorophenol 2137960-04-2

[1310] 1-(2-Fluoro-3-hydroxyphenyl)cyclopropanecarbonitrile 1881320-49-5

[1311] 3-(1-Aminocyclopropyl)-2-fluorophenol 1785193-75-0

[1312] 1-(2-Fluoro-3-hydroxyphenyl)cyclopropanecarboxylic acid 1507131-96-5

[1313] 2-Fluoro-3-(prop-1-en-2-yl)phenol 1375066-38-8

[1314] 3-Cyclopropyl-2-fluorophenol 2290421-25-7

[1315] 2-Fluoro-3-(1-fluorocyclopropyl)phenol 2385918-06-7

[1316] 2-Fluoro-3-vinylphenol 2290411-18-4

[1317] 2-Fluoro-3-[(E)-prop-1-enyl]phenol 2435608-23-2

[1318] 2-Fluoro-3-isopropenylphenol 1375066-38-8

[1319] 3-Ethyl-2-fluorophenol 1243456-02-1

[1320] 2-Fluoro-3-propylphenol 2284409-52-3

[1321] 3-Butyl-2-fluorophenol 2284271-78-7

[1322] Compositions and formulations

[1323] 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.

[1324] Said composition Comprising at least one compound of formula (I) and at least one agriculturally suitable adjuvant, such as a carrier and / or a surfactant.

[1325] Carrieris a solid or liquid, natural or synthetic, organic or inorganic substance that is usually inert. The carrier usually 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, paraffin, alkylbenzenes, xylenes, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or dichloromethane), alcohols or polyols (which may also 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, amides (e.g., dimethylformamide or fatty acid amides) and their esters, lactams (e.g., N-alkylpyrrolidones, especially N-methylpyrrolidone) and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide), oils of plant or animal origin. 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.

[1326] Preferred solid carriers are selected from clay, talc and silica.

[1327] Preferred liquid carriers are selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams and carbonates.

[1328] The amount of the carrier is usually 1 to 99.99% by weight of the composition, preferably 5 to 99.9% by weight, more preferably 10 to 99.5% by weight, and most preferably 20 to 99% by weight.

[1329] The liquid carrier is usually present in the composition in an amount of 20 to 90% by weight, e.g., 30 to 80% by weight.

[1330] The solid carrier is usually present in the composition in an amount of 0 to 50% by weight, preferably 5 to 45% by weight, e.g., 10 to 30% by weight.

[1331] If the composition contains two or more carriers, the range refers to the total amount of the carriers.

[1332] Surfactant It can be an ionic (cationic or anionic), amphoteric or non-ionic surfactant, such as an ionic or non-ionic emulsifier, foaming agent, dispersant, wetting agent, penetration enhancer, and any mixture thereof. Examples of suitable surfactants include, but are not limited to: polyacrylates, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenol sulfonic acid or naphthalene sulfonic acid, condensates of ethylene oxide and / or propylene oxide with fatty alcohols, fatty acids or with fatty amines (e.g., 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 polyoxyethylene ether), salts of sulfosuccinates, taurine derivatives (preferably taurine alkyl esters), 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, lignosulfite waste liquor and methylcellulose. Any mention of salts in this paragraph preferably refers to the respective alkali metal salts, alkaline earth metal salts and ammonium salts.

[1333] Preferred surfactants are selected from polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, alkylbenzene sulfonates such as calcium dodecylbenzene sulfonate, castor oil ethoxylate, sodium lignosulfonate, and arylphenol ethoxylates such as triphenylvinylphenol polyoxyethylene ether.

[1334] The amount of surfactant is usually 5 to 40%, for example 10 to 20%, based on the weight of the composition.

[1335] 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 methyl cellulose (tylose)), thickeners and secondary thickeners (such as cellulose ethers, acrylic derivatives, xanthan gum, modified clays, such as the product available under the name Bentone, and finely divided silica), stabilizers (such as cold stabilizers, preservatives (such as dichlorophen and benzyl alcohol hemiacetal), antioxidants, light stabilizers, especially UV stabilizers or other agents 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, sticking agents, 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.

[1336] The choice of adjuvant depends on 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.

[1337] The compositions of the present invention can be provided to the end user in the form of ready-to-use formulations, i.e., compositions that can be directly applied to plants or seeds by means of suitable equipment such as spraying or dusting devices. Alternatively, the compositions can be provided to the end user in the form of concentrates, which must be diluted before use, preferably with water.

[1338] The compositions 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).

[1339] 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. The amount can vary within a wide range and depends on various factors such as the type of fungi to be controlled, the cultivated plants or materials treated, the climatic conditions and the specific 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 also contain two or more compounds of formula (I). In this case, the ranges given refer to the total amount of the compounds according to the invention.

[1340] The composition according to the invention can be any conventional Composition type , for example solutions (such as aqueous solutions), emulsions, water-based and oil-based suspensions, powders (such as wettable powders, soluble powders), dusts, pastes, granules (such as soluble granules, broadcast granules), suspoemulsion concentrates, natural or synthetic products impregnated with the compound of formula (I), fertilizers and microcapsules in polymers. The compound of formula (I) can be present in suspended, emulsified or dissolved form. Examples of particularly suitable composition types are solutions, water-soluble concentrates (such as SL, LS), dispersible concentrates (DC), suspensions and suspension concentrates (such as SC, OD, OF, FS), emulsifiable concentrates (such as EC), emulsions (such as EW, EO, ES, ME, SE), capsules (such as CS, ZC), pastes, tablets, wettable powders or dusts (such as WP, SP, WS, DP, DS), pressings (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 composition types and other composition types are defined by the Food and Agriculture Organization of the United Nations (FAO). An overview is given in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.

[1341] Preferably, the composition according to the invention is in one of the following forms: EC, SC, FS, SE, OD and WG, more preferably EC, SC, OD and WG.

[1342] More details about the examples of the composition types and their preparation are given below. If there are two or more compounds of the present invention, the amounts of the compounds of the present invention refer to the total amounts of the compounds of the present invention. If there are representatives of any other components of two or more compositions, such as wetting agents, binders, this will apply mutatis mutandis to such components.

[1343] i) Water-soluble concentrates (SL, LS)

[1344] 10 - 60% by weight of at least one compound of formula (I) and 5 - 15% by weight of a surfactant (such as polyoxyethylene fatty alcohol ether) are dissolved in the amount of water and / or water-soluble solvent (such as alcohol, e.g., propylene glycol or carbonate, e.g., propylene carbonate) to obtain a total amount of 100% by weight. Before application, the concentrate is diluted with water.

[1345] ii) Dispersible concentrates (DC)

[1346] 5 - 25% by weight of at least one compound of formula (I) and 1 - 10% by weight of a surfactant and / or binder (such as polyvinylpyrrolidone) are dissolved in the amount of organic solvent (such as cyclohexanone) to obtain a total amount of 100% by weight. Diluting with water gives a dispersant.

[1347] iii) Emulsifiable concentrates (EC)

[1348] 15 - 70% by weight of at least one compound of formula (I) and 5 - 10% by weight of a surfactant (such as a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in the amount of water-insoluble organic solvent (such as aromatic hydrocarbon or fatty acid amide) and if necessary an additional water-soluble solvent to obtain a total amount of 100% by weight. Diluting with water gives an emulsion.

[1349] iv) Emulsions (EW, EO, ES)

[1350] 5 - 40% by weight of at least one compound of formula (I) and 1 - 10% by weight of a surfactant (such as a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20 - 40% by weight of water-insoluble organic solvent (such as aromatic hydrocarbon). The mixture is added to the amount of water by an emulsifier to obtain a total amount of 100% by weight. The resulting composition is a homogeneous emulsion. Before application, the emulsion can be further diluted with water.

[1351] v) Suspensions and suspension concentrates

[1352] v-1) Aqueous-based (SC, FS)

[1353] 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 in the presence of 2 - 10% by weight of a surfactant (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. The amount of water is added to obtain a total of 100% by weight. Diluting with water gives a stable suspension of the active substance. For FS type compositions, up to 40% by weight of a binder (such as polyvinyl alcohol) is added.

[1354] v - 2) Oil - based (OD, OF)

[1355] 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 in the presence of 2 - 10% by weight of a surfactant (such as sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1 - 2% by weight of a thickener (such as modified clay, especially bentonite or silica), and an organic carrier to obtain a fine oil suspension of the active substance. The amount of the organic carrier is added to obtain a total of 100% by weight. Diluting with water gives a stable suspension of the active substance.

[1356] vi) Water - dispersible granules and water - soluble granules (WG, SG)

[1357] 50 - 80% by weight of at least one compound of formula (I) is ground finely in the presence of a surfactant (such as sodium lignosulfonate and polyoxyethylene fatty alcohol ether) and converted into water - dispersible or water - soluble granules by technical equipment (such as extrusion, spray tower, fluidized bed). The surfactant is used in the amount to obtain a total of 100% by weight. Diluting with water gives a stable suspension or solution of the active substance.

[1358] vii) Water - dispersible powders and water - soluble powders (WP, SP, WS)

[1359] 50 - 80% by weight of at least one compound of formula (I) is ground in a rotor - stator mill in the presence of 1 - 8% by weight of a surfactant (such as sodium lignosulfonate, polyoxyethylene fatty alcohol ether) and the amount of a solid carrier (such as silica gel) to obtain a total of 100% by weight. Diluting with water gives a stable suspension or solution of the active substance.

[1360] viii) Gels (GW, GF)

[1361] In a stirred ball mill, 5 - 25% by weight of at least one compound of formula (I) is ground in the presence of 3 - 10% by weight of a surfactant (such as sodium lignosulfonate), 1 - 5% by weight of a binder (such as carboxymethyl cellulose) and the amount of water to give a total of 100% by weight. This gives a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[1362] ix) Microemulsion (ME)

[1363] 5 - 20% by weight of at least one compound of formula (I) is added to 5 - 30% by weight of an organic solvent blend (such as fatty acid dimethylamide and cyclohexanone), 10 - 25% by weight of a surfactant blend (such as polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and the amount of water to give a total of 100% by weight. The mixture is stirred for 1 hour to spontaneously form a thermodynamically stable microemulsion.

[1364] x) Microcapsule (CS)

[1365] 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 hydrocarbon), 2 - 15% by weight of an acrylic monomer (such as methyl methacrylate, methacrylic acid and di- or triacrylate) is dispersed into 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 microcapsules. 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 hydrocarbon) and an isocyanate monomer (such as diphenylmethane - 4,4'-diisocyanate) is dispersed into an aqueous solution of a protective colloid (such as polyvinyl alcohol). Addition of a polyamine (such as hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomer accounts for 1 - 10% by weight of the total CS composition.

[1366] xi) Dustable powder (DP, DS)

[1367] 1 - 10% by weight of at least one compound of formula (I) is finely ground and intimately mixed with the amount of a solid carrier (such as finely divided kaolin) to give a total of 100% by weight.

[1368] xii) Granule (GR, FG)

[1369] 0.5 - 30% by weight of at least one compound of formula (I) is finely ground and combined with the amount of a solid carrier (such as silicate) to give a total of 100% by weight. Granulation is achieved by extrusion, spray tower or fluidized bed.

[1370] xiii) Ultra - low volume liquid (UL)

[1371] Dissolve 1 to 50% by weight of at least one compound of formula (I) in the said amount of organic solvent (such as aromatic hydrocarbons) to obtain a total amount of 100% by weight.

[1372] The composition types i) to xii) may optionally contain other auxiliaries, such as 0.1 to 1% by weight of a preservative, 0.1 to 1% by weight of an antifoaming agent, 0.1 to 1% by weight of a dye and / or pigment, and 5 to 10% by weight of an antifreeze.

[1373] Mixture / combination

[1374] The compounds of formula (I) and the compositions 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, chemical pheromones and / or other agricultural beneficial agents 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.

[1375] Examples of fungicides that can be mixed with the compounds and compositions of formula (I) of the present invention are:

[1376] 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) paclobutrazole, (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-trimethylheptan-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-trimethylheptan-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-trimethylheptan-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-trimethylheptan-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-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-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)oxiranyl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiranyl]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, (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.

[1377] 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-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.(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, (2.060) flubeneteram.

[1378] 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) famoxadon, (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) (2S,3S)-3-(o-tolyl)butan-2-yl N-{[4-methoxy-3-(propanoyloxy)-2-pyridinyl]carbonyl}-L-alaninate.

[1379] 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.

[1380] 5) Compounds capable of having multi-site action, such as (5.001) bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorthalonil, (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.

[1381] 6) Compounds that can induce host defense, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

[1382] 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.

[1383] 8) Inhibitors of ATP production, such as (8.001) silthiofam.

[1384] 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.

[1385] 10) Inhibitors of lipid and membrane synthesis, such as (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[1386] 11) Inhibitors of melanin biosynthesis, such as (11.001) tricyclazole, (11.002) tolprocarb.

[1387] 12) Inhibitors of nucleic acid synthesis, such as (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[1388] 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.

[1389] 14) Compounds capable of acting as uncoupling agents, such as (14.001) fluazinam, (14.002) meptyldinocap.

[1390] 15) Other fungicides selected from (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) 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 its 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) {6-[({(Z)-[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}tert-butyl 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-carbamimidoyl]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.084) N-[(Z)-N-methoxy-C-methyl-carbamimidoyl]-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-trifluoropropanamide, (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}butyramide, (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-benzodioxepin-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-benzodioxepin-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-benzodioxepin-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-benzodioxepin-6-yl methanesulfonate, (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 and (15.127) N-[(2S)-2,4-dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide, (15.128) D-tagatose.

[1391] All the named mixed components of classes (1) to (15) mentioned above can exist in the form of free compounds or, if their functional groups are capable of forming salts, in the form of their agrochemically active salts.

[1392] The compounds and compositions of formula (I) of the present invention can also be combined with one or more biocontrol agents.

[1393] 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.

[1394] As used herein, the term "biocontrol agent" is defined as an organism other than a pest organism for biocontrol purposes and / or a protein or secondary metabolite produced by such an organism. Mutants of the second organism should be included within the definition of biocontrol agents. The term "mutation" refers to variants of the parental strain and methods for obtaining mutants or variants with pesticidal activity greater than that expressed by the parental strain. As used herein, "parental strain" is defined as the original strain before mutation occurs. To obtain the mutants, the parental strain can be treated with chemicals such as N-methyl-N'-nitro-N-nitrosoguanidine, ethyl methanesulfonate, or irradiated with γ-rays, x-rays or ultraviolet light, or by other methods well known to those skilled in the art. Known mechanisms of biocontrol agents include gut bacteria that control root rot by competing for space with fungi on the root surface. 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 toxins in situ.

[1395] "Variant" means a strain having all the identifying characteristics of the NRRL or ATCC accession number described 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.

[1396] "Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex that is stabilized by hydrogen bonds between the bases of nucleotide residues. The hydrogen bonds can be formed by Watson-Crick base pairing, Hoogsteen binding, or any other specific arrangement. The complex can include two strands forming a double-stranded structure, three or more strands forming a multi-stranded complex, a single self-hybridizing strand, or any combination thereof. Hybridization reactions can be carried out under different "stringency" conditions. Generally, low stringency hybridization reactions are carried out in a solution of about 40 °C in 10X SSC or equivalent ionic strength / temperature. Medium stringency hybridization generally occurs under conditions of about 50 °C in 6X SSC, and high stringency hybridization reactions generally occur under conditions of about 60 °C in 1X SSC.

[1397] A variant designated by an NRRL or ATCC accession number can also be defined as a strain whose genomic sequence has a sequence identity greater than 85%, more preferably greater than 90% or more preferably greater than 95% with the genomic sequence of the designated NRRL or ATCC accession number. A polynucleotide or polynucleotide region (or 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, that percentage of bases (or amino acids) is the same when comparing the two sequences. Such alignment and percent homology or sequence identity can be determined using software programs known in the art, e.g., as described in Current Protocols in Molecular biology (F.M. Ausubel et al., eds., 1987).

[1398] NRRL is the abbreviation of the Agricultural Research Service Culture Collection, an international depository for storing microbial strains, internationally recognized for the storage of microorganisms for patent procedure purposes under the Budapest Treaty, located at the National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, Peoria, Illinois 61604, USA.

[1399] ATCC is the abbreviation of the American Type Culture Collection, an international repository for storing microbial strains. It is internationally recognized for the storage of microorganisms for patent procedure purposes under the Budapest Treaty. Its address is the ATCC Patent Depository, 10801 University Boulevard, Manassas, Virginia 10110, USA.

[1400] Examples of biocontrol agents that can be combined with the compounds and compositions of formula (I) of the present invention are:

[1401] (A) Antibacterial agents selected from:

[1402] (A1) Bacteria, such as (A1.1) Bacillus subtilis, especially strain QST713 / AQ713 (SERENADE OPTI or SERENADE ASO obtained from Bayer CropScience LP, US, NRRL accession number B-21661, US Patent No. 6,060,051); (A1.2) Bacillus sp., especially strain D747 (DOUBLE obtained from Kumiai Chemical Industry Co., Ltd.) , accession number FERM BP-8234, US Patent No. 7,094,592; (A1.3) Bacillus pumilus, especially strain BU F-33, with NRRL accession number 5018 (obtained from BASF as part of a product, EPA registration number 71840-19); (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24, accession number DSM 10271 (obtained from Novozymes' or ECO (EPA registration number 70127-5); (A1.5) Paenibacillus sp. strain, accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297; (A1.6) Bacillus subtilis strain BU1814, (obtainable from BASF SE's PLUS, FLEX and (A1.7) Bacillus mojavensis strain R3B (Accession No. NCAIM(P)B001389) (WO 2013 / 034938), produced by Certis USA LLC, a subsidiary of Mitsui & Co.; (A1.8) Bacillus subtilis CX-9060, produced by Certis USA LLC, a subsidiary of Mitsui & Co.; (A1.9) Paenibacillus polymyxa, particularly strain AC-1 (for example, produced by Green Biotech Company Ltd.) );(A1.10) Pseudomonas proradix (for example, produced by Sourcon Padena );(A1.11) Pantoea agglomerans, particularly strain E325 (Accession No. NRRL B-21856) (available from BLOOMTIME BIOLOGICAL of Northwest Agri Products TM FD BIOPESTICIDE); and

[1403] (A2) Fungi, such as (A2.1) Aureobasidium pullulans, particularly blastospores of strain DSM14940, blastospores of strain DSM14941, or a mixture of blastospores of strain DSM14940 and DSM14941 (for example, produced by Bio-Ferm, CH and BLOSSOM );(A2.2) Pseudozyma aphidis (disclosed in WO 2011 / 151819 by Yissum Research Development Company of The Hebrew University of Jerusalem); (A2.3) Saccharomyces cerevisiae, particularly strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938, or CNCM No. I-3939 produced by Lesaffre et Compagnie, FR (WO 2010 / 086790).

[1404] (B) Biofungicides, selected from:

[1405] (B1) Bacteria, such as (B1.1) Bacillus subtilis, particularly strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL accession number B-21661, described in US Patent No. 6,060,051); (B1.2) Bacillus pumilus, particularly strain QST2808 (available from Bayer CropScience LP, US accession number NRRL B-30087, described in US Patent No. 6,245,551); (B1.3) Bacillus pumilus, particularly strain GB34 (available from Bayer AG, DE of Yield ); (B1.4) Bacillus pumilus, particularly strain BU F-33, NRRL accession number 50185 (available as part of the CARTISSA product from BASF, EPA registration number No. 71840-19); (B1.5) Bacillus amyloliquefaciens, particularly strain D747 (available from Kumiai Chemical Industry Co., Ltd. as Double Nickel TM , accession number FERM BP-8234, US Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan, China of WP, registered as a biopesticide in Taiwan, China with registration numbers 4764, 5454, 5096 and 5277); (B1.7) Bacillus subtilis strain MBI 600 (available from BASF SE as SUBTILEX), accession number NRRL B-50595, US Patent No. 5,061,495; (B1.8) Bacillus subtilis strain GB03 (available from Bayer AG, DE of ); (B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24, accession number DSM 10271 (available from Novozymes of 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. of or WG and LifeGard TM)); (B1.11) Bacillus licheniformis, in particular strain SB3086, accession number ATCC 55406, WO 2003 / 000051 (available from Novozymes Biological fungicide and GREEN RELEAF TM )); (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 PLUS, FLEX and EXTRA)); (B1.14) Bacillus amyloliquefaciens CX-9060, produced by Certis USA LLC, a subsidiary of Mitsui & Co.; (B1.15) Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768; WO2014 / 028521) (produced by Marrone Bio Innovations )); (B1.16) Bacillus amyloliquefaciens strain FZB42, accession number DSM 23117 (available from ABiTEP, DE )); (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (produced by FMC Corporation (WG) and (WP)); (B1.18) Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (WO2013 / 034938), produced by Certis USA LLC, a subsidiary of Mitsui & Co.; (B1.19) Paenibacillus polymyxa ssp. plantarum (WO 2016 / 020371), produced by BASF SE; (B1.20) Paenibacillus epiphyticus (WO2016 / 020371), produced by BASF SE; (B.1.21) Pseudomonas chlororaphis strain AFS009, accession number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER produced by AgBiome Innovations, U.S. TM and ); (B1.22) Pseudomonas chlororaphis, especially strain MA342 (e.g., produced by Bioagri and Koppert and ); (B1.23) Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (produced by Novozymes and ); (B1.24) Agrobacterium radiobacter strain K84 (e.g., produced by AgBioChem, CA ); (B1.25) Agrobacterium radiobacter strain K1026 (e.g., NOGALL produced by BASF SE TM ); (B1.26) Bacillus subtilis KTSB strain (produced by Donaghys ); (B1.27) Bacillus subtilis IAB / BS03 (AVIV produced by STK Bio-Ag Technologies TM ); (B1.28) Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan, China WP, registered as a biopesticide with registration numbers 4764, 5454, 5096 and 5277 in Taiwan, China); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN produced by the University of Pretoria TM ); (B1.30) Bacillus methylotrophicus strain BAC-9912 (produced by the Institute of Applied Ecology, Chinese Academy of Sciences); (B1.31) Pseudomonas proradix (e.g., produced by Sourcon Padena ); (B1.32) Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (accession number DSM 7206) (produced by Verdera produced by BioWorks see Crop Protection 2006, 25, 468 - 475); (B1.33) Pseudomonas fluorescens strain A506 (e.g., A506 produced by NuFarm ); and

[1406] (B2) Fungi, such as: (B2.1) Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM-9660; for example produced by Bayer CropScience Biologics GmbH ); (B2.2) Metschnikowia fructicola, especially strain NRRL Y-30752; (B2.3) Microsphaeropsis ochracea; (B2.5) Trichoderma atroviride, especially strain SC1 (accession number CBS 122089, WO 2009 / 116106 and US Patent No. 8,431,120 (produced by 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., produced by Kumiai Chemical Industry Co., Ltd.). ), strain T34 (e.g., T34 Biocontrol provided by Biocontrol Technologies S.L., ES) or strain ICC 012, produced by Isagro; (B2.38) Trichoderma atroviride, strain CNCM I-1237 (e.g., produced by Agrauxine, FR). WP); (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 (IMI 206040); (B2.45) Trichoderma atroviride, strain T11 (IMI 352941 / CECT 20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g., produced by Makhteshim, US). ); (B2.49) Trichoderma asperellum, in particular 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), in particular 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, in particular strain AQ 10 (e.g., AQ provided by IntrachemBio Italia ); (B2.56) Aureobasidium pullulans, in particular blastospores of strain DSM14940; (B2.57) Aureobasidium pullulans, in particular blastospores of strain DSM14941; (B2.58) A mixture of blastospores of Aureobasidium pullulans, in particular 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 rosea f. catenulate) strain J1446 (e.g., provided by Lallemand ); (B2.70) Lecanicillium lecanii (previously known as: Verticillium lecanii) conidia of 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) 11-253151 A; (B2.76) Trichoderma atroviride, strain SKT-2 (FERM P-16511), Japanese Patent Publication (Kokai) 11-253151A; (B2.77) Trichoderma atroviride, strain SKT-3 (FERM P-17021), Japanese Patent Publication (Kokai) 11-253151A; (B2.78) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151CABI, e.g., BioDerma provided by AGROBIOSOL DE MEXICO, S.A. DE C.V.); (B2.79) Trichoderma harzianum, strain DB 103 (e.g., 7456); (B2.80) Trichoderma polysporum, strain IMI 206039 (e.g., Binab TF WP provided by BINAB Bio-Innovation AB, Sweden); (B2.81) Trichodermastromaticum, 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, accession number WCS850, deposited at the Central Bureau for Fungi Cultures (e.g., ); (B2.86) Verticillium chlamydosporium; (B2.87) a mixture of Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012), accession number CABICC IMI 392716 and Trichoderma gamsii (formerly known as Trichoderma viride) strain ICC 080, accession number IMI 392151 (e.g., BIO-TAM from Isagro USA, Inc. TM and Agrobiosol de Mexico, S.A.de C.V. ), (B2.88) Trichoderma asperelloides JM41R (accession number NRRL B-50759) (from BASF SE ); (B2.89) Aspergillus flavus strain NRRL21882 (product name 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 ), 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 viride strain G-41, formerly 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., ); (B2.95) Phlebiopsis gigantea strain VRA 1992 (from Danstar Ferment C); (B2.96) Penicillium steckii (DSM27859; WO 2015 / 067800), from BASF SE; (B2.97) Chaetomium globosum (available from Rivale ); (B2.98) Cryptococcus flavescens, strain 3C (NRRL Y-50378); (B2.99) Dactylaria candida; (B2.100) Dilophosphora alopecuri (available from TWIST ); (B2.101) Fusarium oxysporum, strain Fo47 (available from Natural Plant Protection ); (B2.102) Pseudozyma flocculosa, strain PF-A22 UL (available from Plant Products Co., CA L); (B2.103) Trichoderma gamsii (formerly Trichoderma viride), strain ICC080 (IMI CC 392151CABI) (available from AGROBIOSOL DE MEXICO, 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 NRRL 30548); (B2.106) Simplicillium lanosoniveum.

[1407] Biocontrol agents having the effect of improving plant growth and / or plant health, which can be combined in the compound combinations according to the invention, include

[1408] (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 OPTI or ASO); Bacillus subtilis, especially strain AQ30002 (accession number NRRL B-50421 and described in U.S. Patent Application No. 13 / 330,576); Bacillus subtilis, especially strain AQ30004 (and NRRL B-50455 and described in U.S. 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's ); Bacillus subtilis rm303 (from Biofilm Crop Protection'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; WO 2017 / 205258), Bacillus amyloliquefaciens TJ1000 (available from Novozymes' ); 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 No. NRRL B-5015); a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMCCorporation's (WG), (WP)); Bacillus cereus, especially strain BP01 (ATCC 55675; e.g., produced by Arysta Lifescience, US ); Bacillus subtilis, especially strain MBI 600 (e.g., produced by BASF SE ); Bradyrhizobium japonicum (e.g., produced by Novozymes ); Mesorhizobium ciceri in chickpeas (e.g., NODULATOR produced by BASF SE); Rhizobiumleguminosarium biovar viciae (e.g., NODULATOR produced by BASF SE); Delftia acidovorans, especially strain RAY209 (e.g., produced by Brett Young Seeds ); Lactobacillus sp. (e.g., produced by LactoPAFI ); Paenibacillus polymyxa, especially strain AC-1 (e.g., produced by Green BiotechCompany Ltd. ); Pseudomonas proradix (e.g., produced by Sourcon Padena ); Azospirillum brasilense (e.g., produced by KALO, Inc. ); Azospirillum lipoferum (e.g., VERTEX-IF produced by TerraMax, Inc. TM ); a mixture of Azotobacter vinelandii and Clostridiumpasteurianum (available from Agrinos ) 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., ) and

[1409] (C2) Fungi selected from Purpureocillium lilacinum (formerly known as 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, Talaromyces flavus, 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 bilaiae strain ATCC ATCC20851; 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 No. V08 / 002387, strain No. NMI No. V08 / 002388, strain No. NMI No. V08 / 002389, strain No. NMI No. 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;

[1410] An insecticidal active biocontrol agent selected from

[1411] (D1) Bacteria, selected from Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372; for example, produced by Valent BioSciences of ); Bacillus mycoides, isolate J (for example, BmJ produced by Certis USA LLC, a subsidiary of Mitsui & Co.); Bacillus sphaericus, in particular Serotype H5a5b strain 2362 (strain ABTS-1743) (for example, produced by Valent BioSciences, US of ); Bacillus thuringiensis subsp. kurstaki strain BMP 123, produced by Becker Microbial Products, IL; Bacillus thuringiensis subsp. aizawai, in particular serotype H-7 (for example, produced by Valent BioSciences, US of WG); Bacillus thuringiensis subsp. kurstaki strain HD-1 (for example, produced by Valent BioSciences, US of ES); Bacillus thuringiensis subsp. kurstaki strain BMP123, provided by Becker Microbial Products, IL; Bacillus thuringiensis israelensis strain BMP 144 (for example, provided by Becker Microbial Products IL of ); Burkholderia spp., in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (accession number NRRL B-50319; WO 2011 / 106491 and WO 2013 / 032693; for example, MBI-206TGAI produced by Marrone Bio Innovations and ); Chromobacterium subtsugae, in particular strain PRAA4-1T (MBI-203; for example, produced by Marrone Bio Innovations of ); Paenibacillus popilliae (formerly 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 NB176 (SD-5428; e.g., FC from BioFa DE ); Bacillus thuringiensis var. japonensis strain Buibui; Bacillus thuringiensis var. kurstaki strain ABTS351; Bacillus thuringiensis var. kurstaki strain PB 54; Bacillus thuringiensis var. kurstaki strain SA11; Bacillus thuringiensis var. kurstaki strain SA 12; Bacillus thuringiensis var. kurstaki strain EG2348; 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 MTCC8708); and Wolbachia pipientis strain ZAP (e.g., ZAP from MosquitoMate ); and

[1412] (D2) Fungi, selected from 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 ATCC74250; e.g., ES and ) from Laverlam International Corporation; 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 DSM24665). Among them, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain apopka 97 is particularly preferred;

[1413] (E) Viruses, selected from 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.

[1414] (F) Bacteria and fungi that can be added as "inoculants" to plants or plant parts or plant organs, which, due to their special properties, can promote plant growth and plant health. Examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorius, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., and Streptomyces spp.; and

[1415] (G) Products formed by plant extracts and microorganisms, including proteins and secondary metabolites, can be used as biocontrol agents, such as garlic (Allium sativum), wormwood (Artemisia absinthium), azadirachtin, Biokeeper WP, black cinnamon (Cassia nigricans), Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, male fern (Dryopteris filix-mas), field horsetail (Equisetum arvense), Fortune Aza, Fungastop, Heads Up (saponin extract of Chenopodium quinoa), pyrethrum / pyrethrins, bitterwood (Quassia amara), Quercus, soapbark tree (Quillaja), Regalia, "insecticides", rotenone, ryania / ryanodine, comfrey (Symphytum officinale), tansy (Tanacetum vulgare), thymol, Triact 70, TriCon, nasturtium (Tropaeulum majus), stinging nettle (Urtica dioica), veratrin, mistletoe (Viscum album), extracts of Brassicaceae, especially rapeseed meal or mustard powder, and bioinsecticidal / acaricidal active substances obtained from olive oil, especially unsaturated fats / carboxylic acids with a 16 -C 20 carbon chain length, such as those contained in a product with the trade name .

[1416] The compounds and compositions of formula (I) of the present invention can be combined with one or more active ingredients selected from insecticides, acaricides, and nematicides.

[1417] "Insecticide" and the term "insecticidal" refer to the ability of a substance to increase the mortality rate of insects or inhibit their growth rate. As used herein, the term "insect" includes all organisms in the class "Insecta".

[1418] "Nematicide" and "nematicidal" refer to the ability of a substance to increase the mortality rate of nematodes or inhibit their growth rate. Generally, the term "nematode" includes the eggs, larvae, juveniles, and mature forms of the organisms.

[1419] "Acaricide" and "acaricidal" mean the ability of a substance to increase the mortality rate or inhibit the growth rate of ectoparasites belonging to the class Arachnida, subclass Acari.

[1420] Examples of insecticides, acaricides and nematicides which can be mixed respectively with the compounds and compositions of formula (I) according to the invention are:

[1421] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, e.g., 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, e.g., 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, O-(methoxyaminothiophosphoryl) isopropyl salicylate, isopropylO-(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.

[1422] (2) GABA-gated chloride channel blockers, such as cyclodiene-organochlorines, such as chlordane and endosulfan; or phenylpyrazoles (fiproles), such as ethiprole and fipronil.

[1423] (3) Sodium channel modulators, such as pyrethroids, such as acrinathrin, allethrin, d-cis-trans allethrin, d-transallethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenylisomer), bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomers], deltamethrin, empenthrin [(EZ)-(1R)-isomers], 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.

[1424] (4) Competitive modulators of nicotinic acetylcholine receptors (nAChRs), such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone.

[1425] (5) Allosteric modulators of nicotinic...

Claims

1. The compound of formula (1) and its salts T is O, n is 0 or 1, m is 0 or 1, Provided that when n is 0 and m is 0, then R 6 is a C1-C3-alkoxy or a C1-C3-haloalkoxy, where the C1-C3-alkoxy or C1-C3-haloalkoxy is substituted as defined for R 6 is substituted, R 1 is hydrogen, hydroxy, C1-C6-alkyl or -C(=O)R 10 , wherein R 10 is a C1-C6-alkyl group, R 2 and R 3 is hydrogen, R 4 and R 5 are independently hydrogen or a halogen, R 6 is phenyl, dihydrobenzofuranyl, 1,3 - benzodioxolyl, dihydro - 1,4 - benzodioxenyl, furanyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl or indolyl, wherein the phenyl, dihydrobenzofuranyl, 1,3 - benzodioxolyl, dihydro - 1,4 - benzodioxinyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl or indolyl is optionally substituted with one to three R 6S substituents, wherein R 6S independently represents a halogen, a C1-C6-alkyl group, a C1-C6-haloalkyl group, a C1-C6-alkoxy group, a C2-C6-alkenyl group, a C2-C6-alkynyl group, or a C3-C6-cycloalkyl group, R 7 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl, wherein the C1-C6-alkyl is optionally substituted by one to three R 7Sa substituents wherein R 7Sa is independently halogen, hydroxy or C1-C6-alkoxy, R 8 is hydrogen, halogen, C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkylthio, C3-C8-cycloalkyl, phenyl or phenoxy, wherein The phenoxy group is optionally substituted by 1 to 3 R 8Sc substituents, where R 8Sc independently is C1-C6-haloalkyl, R 9 is hydrogen, a halogen or a cyano group, Q is phenyl, wherein the phenyl group is substituted by one to four substituents Q S substituted Q S independently selected from halogen, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C3-C6-cycloalkyl and oxetanyl.

2. The compound of formula (1) and its salts according to claim 1, wherein T is O, n is 1, m is 0 or 1, R 1 is hydrogen, a C1-C4-alkyl or -C(=O)R 10 , wherein R 10 is a C1-C4-alkyl group, R 2 and R 3 is hydrogen, R 4 and R 5 independently is hydrogen, fluorine or chlorine, R 6 is phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3- dihydro-1,4-benzodioxenyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl or indolyl, wherein the phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl or indolyl is optionally substituted with one to three R 6S substituents, wherein R 6S is independently halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, R 7 is hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, wherein the C1-C4-alkyl is optionally substituted by one or two R 7Sa substituents, wherein R 7Sa is a C1-C4-alkoxy group, R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl or phenyl, R 9 is hydrogen, fluorine, chlorine or a cyano group, Q is phenyl, wherein the phenyl group is substituted by one to three substituents Q S substituted, wherein Q S independently selected from halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C3-C6-cycloalkyl and oxetanyl.

3. The compound of formula (1) according to claim 1 or 2, wherein R 1 is hydrogen, n is 1, m is 0 or 1, R 2 and R 3 is hydrogen, R 4 and R 5 are independently hydrogen or a halogen.

4. The compound of formula (1) according to claim 1 or 2, wherein R 6 is phenyl, 1,3 - benzodioxol - 5 - yl, 2,3 - dihydro - 1,4 - benzodioxin - 6 - yl, furan - 2 - yl, thiophene - 2 - yl, thiophene - 3 - yl, pyrazol - 1 - yl, pyrimidin - 2 - yl, pyrimidin - 5 - yl, indol - 3 - yl, indol - 4 - yl or indol - 5 - yl, wherein phenyl, 1,3-benzodioxol-5-yl, 2,3-dihydro-1,4-benzodioxin-6-yl, furan-2-yl, thiophene-2-yl, thiophene-3-yl, pyrazol-1-yl, pyrimidin-2-yl, pyrimidin-5-yl, indol-3-yl, indol-4-yl or indol-5-yl is optionally substituted by one or two substituents independently selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl and C3-C6-cycloalkyl.

5. The compound of formula (1) according to claim 1 or 2, wherein R 7 is chlorine, iodine, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, R 8 is hydrogen, halogen or C1-C4-alkyl.

6. The compound of formula (1) according to claim 1 or 2, wherein Q is phenyl, wherein the phenyl group is substituted with one to three substituents Q S substituted, wherein Q S independently selected from halogen, nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C3-C6-cycloalkyl.

7. A composition for controlling phytopathogenic harmful fungi, which comprises at least one compound of formula (I) according to any one of claims 1 to 6, and at least one carrier and / or surfactant.

8. 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 6 and / or the composition according to claim 7 to harmful microorganisms and / or their habitats.

9. Use of the compound of formula (I) according to any one of claims 1 to 6 for controlling harmful microorganisms in crop protection and material protection.

10. A method for preparing the compound of formula (I-a) where m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and Q are as defined in any one of claims 1 to 6, and T is O, comprising the step of reacting a compound of formula (1) wherein R 7 、R 8 、R 9 and Q are as defined in any one of claims 1 to 6, and U 1 is a hydroxyl group, a halogen, or C 1 -C 6 -alkoxy group, with an amine of formula (2) or its salt, where m, n, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in any one of claims 1 to 6.

11. A method for preparing the compound of formula (I-a-1) where m, n, R 2 , R 3 , R 4 , R 5 , R 6 , R 9 and Q are as defined in any one of claims 1 to 6, and T is O, R 1 is hydrogen, hydroxy, cyano, C1-C6-alkyl or C1-C6-alkoxy, R 7 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy, R 8 is hydrogen, halogen or C1-C6-alkyl, comprising the step of reacting a compound of formula (3) where m, n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 as defined in any one of claims 1 to 6, and X is halogen, with a compound of formula (4) in the presence of an organic or inorganic base wherein Q is as defined in any one of claims 1 to 6.

12. The compound of formula (3), wherein n is 1, m is 1, R 1 is hydrogen, R 2 and R 3 is hydrogen, R 4 and R 5 are independently hydrogen or fluorine, The condition is R 4 and R 5 at least one of which is not hydrogen, R 6 is phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3- dihydro-1,4-benzodioxenyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl or indolyl, wherein phenyl, 2,3-dihydrobenzofuranyl, 1,3-benzodioxolyl, 2,3-dihydro-1,4-benzodioxinyl, furyl, pyrazolyl, thienyl, pyridyl, pyrimidinyl and indolyl are optionally substituted with one to three R 6S substituents, wherein R 6S is independently halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl or C3-C6-cycloalkyl, R 7 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl or C3-C6-cycloalkyl, wherein the C1-C4-alkyl is optionally substituted by one or two R 7Sa substituents, where R 7Sa is independently a C1-C4-alkoxy group, R 8 is hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-alkylthio, C3-C6-cycloalkyl or phenyl, R 9 is hydrogen or a halogen, X is halogen, provided that the compound of formula (3) is not: 5-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]-2-(trifluoromethyl)isonicotinamide 3-chloro-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide 3-bromo-N-[2-(2,4-dichlorophenyl)-2,2-difluoroethyl]isonicotinamide.

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