Azabicyclo substituted heterocyclic compounds as fungicides

Abstract

The present disclosure relates to azabicyclic substituted heterocyclic compounds of formula (1), wherein A 1 、A 2 ,m,R 3 、R 4 、R 5 , L, R 6 ,T,ringY,p,R 7 and Q have the meanings as defined in the specification, and relate to compositions comprising such compounds, their preparation methods and intermediates, and their use in controlling phytopathogenic microorganisms such as phytopathogenic fungi.

Description

[0001] The present invention relates to azabicyclic-substituted heterocyclic compounds and their use in controlling plant pathogenic microorganisms such as plant pathogenic fungi, and also relates to methods and intermediates for preparing these compounds.

[0002] To date, many crop protection agents have been developed to combat or prevent microbial infestation. However, there is still a need to develop new compounds that are effective against a broad spectrum of plant pathogenic microorganisms (e.g., fungi) and that have low toxicity, high selectivity, or can be used at low application rates while still providing effective pest control. New compounds are also desirable to prevent the development of resistance.

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

[0004] Compounds of formula (I)

[0005] The present invention relates to compounds of formula (I) and their N-oxides, salts, hydrates and hydrates of said salts and N-oxides:

[0006]

[0007] in

[0008] A 1 N or CR 8 ,

[0009] A 2 For O, S, C(=O), S(=O), S(=O)2, NR 1 or CR 2A R R2B ,

[0010] in

[0011] R 1 、R 2A and R 2B are independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl, wherein C1-C6-alkyl is optionally substituted by 1 to 3 groups independently selected from halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, C1-C6-alkoxy, C1-C 6-

[0012] Halogenated alkoxy, C1-C 6- substituted by alkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic groups,

[0013] and

[0014] wherein the C3-C8-cycloalkyl radical is optionally substituted by 1 to 3 radicals independently selected from halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C 6- Halogenated alkoxy, C2-C 6- substituted by alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,

[0015] or

[0016] R 2A and R 2B Together with the carbon atoms to which they are attached, they form a C3-C8-cycloalkyl-ring or

[0017] 3- to 7-membered heterocyclyl-ring,

[0018] m is 0, 1, or 2,

[0019] R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxy, formyl, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylcarbonyl, C1-C 6- Alkoxycarbonyl, C2-C6-alkenyl, C2-C 6- Alkynyl, C3-C8-cycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or -O-Si(C1-C6-alkyl)3, wherein C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylcarbonyl, C1-C 6- Alkoxycarbonyl, C2-C6-alkenyl, C2-C 6- Alkynyl and -O-Si(C1-C6-alkyl) 3- optionally substituted by 1 to 3 substituents independently selected from halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl,

[0020] and

[0021] Among them, C3-C8-cycloalkyl, C6-C 14-aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted by 1 to 3 independently selected from halogen, cyano, nitro, hydroxy, formyl, oxo, methylene (methylidene), C1-C6-alkyl, C1-C 6- Halogenated alkyl, C1-C6-alkoxy, C1-C 6- Halogenated alkoxy, C2-C 6- alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl 、 -O-Si(C1-C6-alkyl)3 and a 3- to 7-membered heterocyclic group,

[0022] or

[0023] R 3 and R 4 Together with the carbon atoms to which they are attached, they form a carbonyl group, a methylene group, a C3-C8 cycloalkyl ring or a 3- to 7-membered heterocyclyl ring,

[0024] wherein the C3-C8-cycloalkyl ring and the 3- to 7-membered heterocyclyl ring are optionally substituted by 1 to 3 groups independently selected from halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, C1-C6-alkyl, C1-C 6- Halogenated alkyl, C1-C6-alkoxy, C1-C 6- Halogenated alkoxy, C2-C 6- is substituted by a substituent selected from the group consisting of alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic groups, R 5 is hydrogen, hydroxy, C1-C6-alkyl, C1-C6-alkoxy, C1-C 6- Alkylcarbonyloxy, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C 6- Alkylsulfonyl, C3-C8-cycloalkyl or -O-Si(C1-C6-alkyl)3,

[0025] Among them, C1-C6-alkyl, C1-C6-alkoxy, C1-C 6- Alkylcarbonyloxy, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl and -O-Si(C1-C6-alkyl)3 are optionally substituted by 1 to 3 groups independently selected from halogen, cyano, amino, nitro, hydroxy, formyl, carboxyl, C1-C6-alkoxy, C1-C6- 6- Halogenated alkoxy, C1-C6-alkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halogenated cycloalkyl,

[0026] -O-Si(C1-C6-alkyl)3 and a 3- to 7-membered heterocyclic substituent,

[0027] and

[0028] wherein the C3-C8-cycloalkyl radical is optionally substituted by 1 to 3 radicals independently selected from halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C 6- Halogenated alkoxy, C2-C 6- alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl

[0029] Substituents substituted by

[0030] or

[0031] R 3 and R 5 or R 4 and R 5 together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl ring,

[0032] T is hydrogen, hydroxy, C1-C6-alkyl, -C(=O)R 9 、-C(=O)(OR 10 ),

[0033] -C(=O)N(R 11 )2、-S(=O)R 12 、-S(=O)2R 13 or -S(=O)2N(R 14 )2, where

[0034] R 9 and R 10 are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[0035] R 11 、R 12 、R 13 and R 14 are independently hydrogen, C1-C6-alkyl, C1-C 6- Halogenated alkyl, C3-C8-cycloalkyl or C2-C6-alkenyl, L is a direct bond, carbonyl, C1-C6-alkylene, C2-C6-alkenylene, C2-C6-alkyne

[0036] -C(=O)-C1-C6-alkylene-, -C1-C6-alkylene-C(=O)-, -NR L1 -、

[0037] -NR L2(C=O)-, -C(=O)NR L3 -、-NR L4 S(=O)2-、-S(=O)2NR L5 -、

[0038] -C(=NOR L6 )-、-C(=NN(R L7 )2)-、-C(=NR L8 )- or a group of the formula

[0039]

[0040] in

[0041] The C1-C6-alkylene, C2-C6-alkenylene, C2-C6-alkynylene, -C(=O)-C1-C6-alkylene- and -C1-C6-alkylene-C(=O)- are optionally substituted by 1 to 3 substituents L SA replaced by

[0042] # is the point of attachment to the heterocyclic moiety,

[0043] ##For R 6 Connect the dots,

[0044] L 1 is a direct bond or a C1-C6-alkylene group,

[0045] L 2 is a direct bond or a C1-C6-alkylene group,

[0046] E is a C3-C8-cycloalkyl group, a C3-C8-cycloalkenyl group or a 3- to 7-membered heterocyclic group,

[0047] wherein the C3-C8 cycloalkyl, C3-C8 cycloalkenyl and 3- to 7-membered heterocyclic groups are optionally substituted by 1 to 3 substituents L SC replaced by

[0048] R L1 、R L2 、R L3 and R L4 are independently hydrogen or C1-C6-alkyl,

[0049] R L5 、R L6 、R L7 and R L8 are independently hydrogen, C1-C6-alkyl, C1-C 6- haloalkyl, C3-C8-cycloalkyl or C2-C6-alkenyl,

[0050] L SAare independently halogen, cyano, hydroxy, carboxyl, methylene, halogenated methylene, C1-C6-alkoxy, C1-C 6- haloalkoxy, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, C1-C6-alkoxycarbonyl, -O-Si(C1-C6-alkyl)3 or 3- to 7-membered heterocyclyl,

[0051] and / or

[0052] Two substituents L bonded to the same carbon atom SA together with the carbon atoms to which they are attached form a C3-C8 cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,

[0053] L SC are independently halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C 6- Halogenated alkyl, C1-C6-alkoxy, C1-C 6- Halogenated alkoxy, C2-C 6- alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 or 3- to 7-membered heterocyclyl, and / or

[0054] Two Ls SC The substituents together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl-ring,

[0055] R 6 C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic, 5- to 14-membered

[0056] Heteroaryl, C3-C 12 -Carbocyclyloxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C3-C 12 -Carbocyclylsulfanyl, C6-C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C3-C 12 -Carbocyclic sulfinyl, C6-C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclylsulfinyl, C3-C 12 -Carbocyclic sulfonyl, C6-C 14-arylsulfonyl, 5- to 14-membered heteroarylsulfonyl, 3- to 14-membered heterocyclylsulfonyl, C1-C3-alkoxy, C1-C3-haloalkoxy, C1-C3-alkylsulfanyl, C1-C3-alkylsulfinyl or C1-C3-alkylsulfonyl,

[0057] wherein C1-C3-alkoxy, C1-C3-haloalkoxy, C1-C3-alkylsulfanyl, C1-C3-alkylsulfinyl and C1-C3-alkylsulfonyl are replaced by a C1-C3-alkylsulfonyl group. 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic and 5- to 14-membered heteroaryl substituents,

[0058] wherein the C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl, which in turn are optionally substituted with 1 to 4 R 6S Substituted by a substituent, wherein C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C 12 -Carbocyclyloxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C3-C 12 -Carbocyclylsulfanyl, C6-C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C3-C 12 -Carbocyclic sulfinyl, C6-C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclylsulfinyl, C3-C 12 -Carbocyclic sulfonyl, C6-C 14 -arylsulfonyl, 5- to 14-membered heteroarylsulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with 1 to 4 R 6S Substituted by a substituent,

[0059] in

[0060] R 6Sindependently selected from halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylene, halomethylene, formyl, 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, C2-C6-alkynyloxy, C2 -C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- to 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -N(R 15 )2, -O(C=O)R 16 、-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 and -Si(C1-C6-alkyl)3,

[0061] wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and

[0062] -Si(C1-C6-alkyl)3 is further optionally substituted by 1 to 3 groups independently selected from cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy,

[0063] -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halogenated cycloalkyl and 3- to 7-membered heterocyclic substituents, or

[0064] Two C1-C6-alkyl substituents attached to the same carbon atom form together with the carbon atom to which they are attached a C3-C8-cycloalkyl-ring,

[0065] and

[0066] Among them, C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5- to 6-membered heteroaryl and 3- to 7-membered heterocyclyl are further optionally substituted by 1 to 4 independently selected from halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-

[0067] Alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-

[0068] Halogenated alkoxycarbonyl, C2-C 6- alkenyl, C3-C8-cycloalkyl and C3-C8-

[0069] is substituted by a halocycloalkyl substituent,

[0070] and among them

[0071] R 15 are independently hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl,

[0072] wherein the C1-C6-alkyl is in turn optionally substituted by 1 to 3 groups independently selected from halogen, cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy,

[0073] -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl,

[0074] C3-C8-halocycloalkyl and 3- to 7-membered heterocyclic substituents, and

[0075] wherein the C3-C8-cycloalkyl is in turn optionally substituted by 1 to 4 groups independently selected from halogen, cyano, nitro, hydroxy, formyl, carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl,

[0076] C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl,

[0077] C1-C6-halogenated alkoxycarbonyl, C2-C 6-alkenyl, C3-C8-cycloalkyl and

[0078] substituted by a C3-C8-halocycloalkyl substituent,

[0079] R 16 、R 17 、R 18 and R 19 are independently hydrogen, C1-C6-alkyl or C1-C 6-

[0080] haloalkyl,

[0081] wherein the C1-C6-alkyl and C1-C 6- The haloalkyl group is in turn optionally replaced by 1 to 3 groups independently selected from cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl),

[0082] -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halogenated cycloalkyl and 3- to 7-membered heterocyclic groups, ring Y forms a bicyclic heterocyclic group or a bicyclic heteroaryl group together with the pyridine ring or the pyridazine ring, p is 0, 1, 2, 3 or 4,

[0083] R 7 For hydrogen, halogen, cyano, isocyano, hydroxyl, thiol, nitro, amino, formyl

[0084] alkyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkynyloxy, C2-C6-haloalkynyloxy, C1-C6-alkylsulfanyl, C1-C6-alkylthioalkyl ...thioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthioalkyl, C1-C6-alkylthio -C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C2-C6-alkenylsulfanyl, C2-C6-alkynylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, C3-C8-cycloalkyloxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkane)3, -N(R 20 )2、-C(=NR 21 )R22 、-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 ,

[0085] C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, 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-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C2-C6-alkenylsulfanyl, C2-C6-alkynylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3 and -Si(C1-C6-alkyl)3 are optionally substituted by 1 to 3 R 7Sa Substituent substitution,

[0086] wherein C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl and C3-C8-cycloalkyloxy are optionally substituted by 1 to 3 R 7Sc Substituents are substituted, and wherein

[0087] R 20 are independently 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 or 3- to 7-membered heterocyclyl, wherein 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 or 3- to 7-membered heterocyclyl, 6- Halogenated alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C 6- Halogenated alkenyl, C2-C 6- Alkynyl and C2-C6-haloalkynyl are in turn optionally substituted by 1 to 3 R 7Sa Substituent substitution,

[0088] and

[0089] wherein C3-C8-cycloalkyl, C3-C8-halocycloalkyl and 3- to 7-membered heterocyclyl are in turn optionally substituted by 1 to 3 substituents R 7Sc replace,

[0090] 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

[0091] -(C1-C6-alkyl)amino,

[0092] Among them, C1-C6-alkyl, C1-C 6- Halogenated alkyl, C1--C6-alkoxy, mono

[0093] -(C1-C6-alkyl)amino and di-(C1-C6-alkyl)amino are in turn optionally substituted with 1 to 3 R 7Sa Substituent substitution,

[0094] R 23 、R 24 、R 25 、R 26 、R 27 、R 28 and R 29 are independently hydrogen, C1-C6-alkyl,

[0095] C1-C6-haloalkyl and C3-C8-cycloalkyl,

[0096] wherein C1-C6 alkyl and C1-C6 haloalkyl are optionally replaced by 1 to 3 R 7Sa Substituent substitution,

[0097] and

[0098] wherein the C3-C8-cycloalkyl group is in turn optionally replaced by 1 to 3 R 7Sc Substituent substitution,

[0099] in

[0100] R 7Sa are independently 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 or 3- to 7-membered heterocyclyl,

[0101] R 7Scare independently halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C 6- alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 or 3- to 7-membered heterocyclyl,

[0102] or

[0103] Two R attached to the same carbon atom 7Sc The substituents together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl-ring,

[0104] R 8 is hydrogen or halogen,

[0105] Q is C6-C 14 -aryl, C3-C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered

[0106] heteroaryl,

[0107] Among them, C6-C 14 -aryl, C3-C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl optionally substituted by 1 to 5 substituents Q S replace,

[0108] in

[0109] Q S independently selected from halogen, cyano, isocyano, nitro, hydroxyl, mercapto, methyl

[0110] Acyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C 6- Alkenyl, C2-C 6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, C6-C 14-aryl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3,

[0111] -Si(C1-C6-alkyl)3, -OC(=O)R 30 、

[0112] -NR 31 C(=O)R 32 、-C(=O)N(R 33 )2、C(=S)R 34 、-C(=S)N(R 35 )2.

[0113] -C(=NR 36 )R 37 、-C(=NOR 38 )R 39 and -N(R 40 )2,

[0114] in

[0115] 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-C 6- Alkenyl, C2-C 6- haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl-

[0116] , -O-Si(C1-C6-alkyl)3 and -Si(C1-C6-alkyl)3 are in turn optionally substituted by 1 to 3 substituents independently selected from cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl, and said C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C6-cycloalkenyl,

[0117] The 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl are in turn optionally substituted by 1 to 3 groups 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-C 6- substituted by alkenyl and 3- to 7-membered heterocyclic substituents,

[0118] wherein the C3-C8-cycloalkyl, C3-C 8- The halocycloalkyl and 3- to 7-membered heterocyclyl are further optionally substituted by two substituents which, together with the carbon atoms to which they are attached, form a C3-C8-cycloalkyl group, and wherein

[0119] R 30 、R 31 、R 32 、R 33 、R 34 、R 35 、R 36 、R 37 、R 38 and R 39

[0120] are independently hydrogen, C1-C6-alkyl, C1-C 6- haloalkyl or C1-C6-alkoxy,

[0121] in

[0122] The C1-C6-alkyl, C1-C 6- The haloalkyl and C1-C6-alkoxy groups are in turn optionally replaced by 1 to 3 groups 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 4-Ci-alkyl.

[0123] The substituents of the 7-membered heterocyclic group are substituted, wherein

[0124] R 40 is hydrogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C 6- Alkenyl, C2-C 6- haloalkenyl or C3-C8-cycloalkyl,

[0125] wherein the C1-C6-alkyl, C1-C 6-Halogenated alkyl, C1-C6-alkoxy, C2-C 6- Alkenyl and C2-C 6- The haloalkenyl group is in turn optionally substituted by 1 to 3 groups independently selected from cyano, amino, nitro, hydroxy, C1-C6-alkoxy, C1-C6- 6- Haloalkoxy, C1-C6-alkoxycarbonyl, C1-C 6- substituted with a substituent selected from the group consisting of a haloalkoxycarbonyl group, a C3-C8-cycloalkyl group, a C3-C8-halocycloalkyl group, -Si(C1-C6-alkyl)3 group, and a 3- to 7-membered heterocyclyl group, and

[0126] wherein the C3-C8-cycloalkyl is in turn optionally substituted by 1 to 3 groups independently selected from halogen, cyano, amino, nitro, hydroxy, formyl,

[0127] Carboxyl, oxo, methylene, halomethylene, C1-C6-alkyl,

[0128] C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl,

[0129] C3-C8-cycloalkyl, C3-C8-halogenated cycloalkyl, C2-C 6- Substituents of alkenyl and 3- to 7-membered heterocyclic groups,

[0130] wherein the C3-C8-cycloalkyl, C3-C 8- Halogenated cycloalkyl and 3-

[0131] to 7-membered heterocyclic group is further optionally substituted with two substituents,

[0132] The two substituents together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl group,

[0133] or

[0134] Two Q bonded to the same carbon atom S The substituents together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring.

[0135] The invention also relates to compositions comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable adjuvant.

[0136] 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.

[0137] The present invention also 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 plants, plant parts, seeds, fruits or soil in which the plants to be treated are growing.

[0138] The present invention also relates to processes and intermediates for preparing compounds of formula (I).

[0139] Unless otherwise stated, the following definitions apply to substituents and residues used throughout the specification and claims:

[0140] As used herein, the term "halogen" refers to a fluorine, chlorine, bromine, or iodine atom.

[0141] As used herein, the term "methylidene" refers to a CH2 group attached to a carbon atom via a double bond.

[0142] As used herein, the term "halomethylene" refers to a CX2 group attached to a carbon atom via a double bond, wherein X is a halogen.

[0143] As used herein, the term "oxo" refers to an oxygen atom bonded to a carbon atom or a sulfur atom through a double bond.

[0144] As used herein, the term "formyl" refers to -CH(=0).

[0145] As used herein, the term "C1-C6-alkyl" refers to a branched or straight saturated hydrocarbon chain having 1, 2, 3, 4, 5, or 6 carbon atoms. Examples of C1-C6-alkyl include, but are not limited to, methyl, ethyl, propyl (n-propyl), 1-methylethyl (isopropyl), butyl (n-butyl), 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1,2-dimethylpropyl, 1,2-dimethylbutyl ... In some embodiments, 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.

[0146] As used herein, the term "C1-C6-haloalkyl" refers to a C1-C6 alkyl as defined above in which one or more hydrogen atoms are replaced by one or more identical or different halogen atoms. 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.

[0147] As used herein, the term "C1-C 6- "Fluoroalkyl" means a C1-C6-alkyl group as defined above in which one or more hydrogen atoms are replaced by one or more identical or different fluorine atoms. Examples of C1-C6-fluoroalkyl groups include, but are not limited to, monofluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl and 2,2,2-trifluoroethyl.

[0148] As used herein, the term "C1-C6-alkylene" refers to a divalent C1-C6-alkyl group as defined herein. Examples of C1-C6-alkylene groups include, but are not limited to, methylene, ethylene, propyl-1,3-ene, propyl-1,2-ene, butyl-1,4-ene, butyl-1,3-ene, butyl-1,2-ene, 1,5-pentylene, and 1,6-hexylene.

[0149] As used herein, the terms "C3-C8-cycloalkyl" and "C3-C8-cycloalkyl-ring" refer to a monocyclic saturated hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms. Examples of C3-C8-cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. In particular, the cycloalkyl group has 3 to 6 carbon atoms.

[0150] As used herein, the term "C3-C8 halocycloalkyl" refers to a saturated hydrocarbon ring system in which all ring members (varying from 3 to 8) are carbon atoms, and in which 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 "C2-C6-alkenyl" refers to a branched or straight unsaturated hydrocarbon chain having 2, 3, 4, 5, or 6 carbon atoms and containing at least one double bond. Examples of C2-C6-alkenyl groups 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 ... -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-methyl Pent-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 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.

[0152] As used herein, the term "C2-C6-alkynyl" refers to a branched or straight 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. 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.

[0153] As used herein, the term "C2-C6-haloalkenyl" refers to a C2-C6-alkenyl group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different.

[0154] The term "C2-C6-haloalkynyl" as used herein means a C2-C6-alkynyl group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different.

[0155] As used herein, the term "C1-C6-alkoxy" refers to a group of the formula (C1-C6-alkyl)-O-, wherein the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, n-hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 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. This definition also applies to alkoxy as part of a composite substituent, for example alkoxyalkyl, alkoxyalkoxy, unless defined elsewhere.

[0156] As used herein, the term "C1-C6-haloalkoxy" refers to a C1-C6-alkoxy group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different. Examples of C1-C6-haloalkoxy groups 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-trifluoroprop-2-oxy.

[0157] As used herein, the term "C1-C6-hydroxyalkyl" refers to a C1-C6-alkyl group as defined above in which at least one hydrogen atom is replaced by a hydroxy group. Examples of C1-C6-hydroxyalkyl groups include, but are not limited to, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 1-hydroxypropyl, 1-hydroxypropan-2-yl, 2-hydroxypropan-2-yl, 2,3-dihydroxypropyl, and 1,3-dihydroxypropan-2-yl.

[0158] As used herein, the term "C3-C8-cycloalkoxy" refers to a monocyclic, saturated cycloalkoxy group having 3 to 8, preferably 3 to 6, carbon ring members, such as, but not limited to, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy. Unless otherwise defined, this definition also applies to cycloalkoxy groups that are part of a composite substituent, such as, for example, cycloalkoxyalkyl.

[0159] As used herein, the term "C3-C8-halocycloalkoxy" refers to a C3-C8-cycloalkoxy group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0160] As used herein, the term C2-C6-alkenyloxy refers to the formula (C2-C6-alkenyl)-O-, wherein the term "C1-C6-alkenyl" group is as defined herein. Examples of C2-C6-alkenyloxy include, but are not limited to, vinyloxy (or "ethoxy"), prop-2-en-1-yloxy (or "allyl"), prop-1-en-1-oxy, but-3-enyloxy, but-2-enyloxy, but-1-enyloxy, pent-4-enyloxy, pent-3-enyloxy, pent-2-enyloxy, pent-1-enyloxy, hex-5-enyloxy, hex-4-enyloxy, hex-3-enyloxy, hex-2-enyloxy, hex-1-enyloxy, prop-1-en-2-oxy (or "isopropenyloxy"), 2-methylprop-2-enyloxy, 1-methylprop-2-enyloxy, 2-methylprop-1-enyloxy oxy, 1-methylprop-1-enyloxy, 3-methylbut-3-enyloxy, 2-methylbut-3-enyloxy, 1-methylbut-3-enyloxy, 3-methylbut-2-enyloxy, 2-methylbut-2-enyloxy, 1-methylbut-2-enyloxy, 3-methylbut-1-enyloxy, 2-methylbut-1-enyloxy, 1-methylbut-1-enyloxy, 1,1-dimethylprop-2-enyloxy, 1-ethylprop-1-enyloxy, 1-propylvinyloxy, 1-isopropylvinyloxy, 4-methylpent-4-enyloxy, 3-methylpent-4-enyloxy, 2-methylpent-4-enyloxy, 1-methylpent-4-enyloxy oxy, 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 1-ethylbut-1-enyloxy, 2-propylprop-2-enyloxy, 1-propylprop-2-enyloxy, 2-isopropylprop-2-enyloxy, 1-isopropylprop-2-enyloxy, 2-propylprop-1-enyloxy, 1-propylprop-1-enyloxy, 2-isopropylprop-1-enyloxy, 1-isopropylprop-1-enyloxy, 3,3-dimethylprop-1-enyloxy, 1-(1,1-dimethylethyl)vinyloxy, buta-1,3-dienyloxy, penta-1,4-dienyloxy, hexa-1,5-dienyloxy or methylhexadienyloxy.

[0161] The term "C2-C6-haloalkenyloxy" as used herein means that one or more hydrogen atoms in the group of formula (C2-C6-alkenyl)-O- as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0162] As used herein, the term "C2-C6-alkenylene" refers to a divalent C2-C6-alkenyl group as defined herein. Examples of C2-C6-alkenylene groups include, but are not limited to, vinylene, 1,3-propenylene, butenylene, pentenylene, hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecenylene, and the like.

[0163] As used herein, the term "C2-C 6- "Haloalkynyloxy" means that one or more hydrogen atoms in a (C2-C6-alkynyl)-O- group as defined above are replaced by one or more halogen atoms, which may be the same or different.

[0164] As used herein, the term "C1-C6-alkylsulfanyl" refers to a linear or branched saturated radical of the formula (C1-C6-alkyl)-S-, wherein the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkylsulfanyl include, but are not limited to, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, sec-butylsulfanyl, isobutylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, and hexylsulfanyl.

[0165] As used herein, the term "C1-C6-haloalkylsulfanyl" refers to a C1-C6-alkylsulfanyl group as defined above in which one or more hydrogen atoms are substituted by one or more halogen atoms, which may be the same or different.

[0166] As used herein, the term "C3-C8-cycloalkylsulfanyl" refers to a monovalent, monocyclic saturated hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms and bonded to the backbone via a sulfur atom. Examples of monocyclic C3-C8-cycloalkylsulfanyl include, but are not limited to, cyclopropylsulfanyl, cyclobutylsulfanyl, cyclopentylsulfanyl, cyclohexylsulfanyl, cycloheptylsulfanyl, or cyclooctylsulfanyl.

[0167] As used herein, the term "C1-C6-alkylsulfinyl" refers to a straight-chain or branched saturated group of the formula (C1-C6-alkyl)-S(=O)-, wherein the term "C1-C6-alkyl" is as defined herein. Examples of C1-C6-alkylsulfinyl groups include, but are not limited to, linear or branched saturated alkylsulfinyl groups having 1 to 8, preferably 1 to 6, and more preferably 1 to 4 carbon atoms, such as, but not limited to, C1-C6-alkylsulfinyl groups, 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-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 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.

[0168] The term "C1-C6-haloalkylsulfinyl" as used herein means a C1-C6-alkylsulfinyl group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different.

[0169] As used herein, the term "C3-C8-cycloalkylsulfinyl" refers to a saturated, monovalent, monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms and bonded to the backbone via a -S(=O)- group. Examples of monocyclic C3-C8-cycloalkylsulfinyl groups include, but are not limited to, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, cycloheptylsulfinyl, or cyclooctylsulfinyl.

[0170] As used herein, the term "C1-C6-alkylsulfonyl" refers to a linear or branched saturated group of the formula (C1-C6-alkyl)-S(=O)2-, wherein 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.

[0171] The term "C1-C6-haloalkylsulfonyl" as used herein means a C1-C6-alkylsulfonyl group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0172] As used herein, the term "C3-C8-cycloalkylsulfonyl" refers to a monovalent, monocyclic saturated hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms and bonded to the backbone via a -S(=O)2- group. Examples of monocyclic C3-C8-cycloalkylsulfonyl groups include, but are not limited to, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cycloheptylsulfonyl, or cyclooctylsulfonyl.

[0173] The term "C1-C6-alkylcarbonyl" as used herein refers to a straight-chain or branched saturated group of the formula (C1-C6-alkyl)-C(=O)-, wherein the term "C1-C6-alkyl" is as defined herein.

[0174] The term "C1-C6-haloalkylcarbonyl" as used herein means a C1-C6-alkylcarbonyl group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different.

[0175] As used herein, the term "C1-C6-alkylcarbonyloxy" refers to a saturated, straight-chain or branched group of the formula (C1-C6-alkyl)-C(=O)O-, wherein the term "C1-C6-alkyl" is as defined herein.

[0176] As used herein, the term "C1-C6-alkoxycarbonyl" refers to a saturated, linear or branched group of the formula (C1-C6-alkoxy)-C(=O)-, wherein the term "C1-C6-alkoxy" is as defined herein.

[0177] The term "C1-C6-haloalkoxycarbonyl" as used herein means a C1-C6-alkoxycarbonyl group as defined above in which one or more hydrogen atoms are replaced by one or more halogen atoms which may be the same or different.

[0178] As used herein, the term "mono-(C1-C6-alkyl)amino" refers to an amino group having one C1-C6-alkyl group as defined herein. Examples of mono-(C1-C6-alkyl)amino groups include, but are not limited to, N-methylamino, N-ethylamino, N-isopropylamino, N-n-propylamino, N-isopropylamino, and N-tert-butylamino.

[0179] As used herein, the term "di-(C1-C6)-alkylamino" refers to an amino group having two independently selected C1-C6-alkyl groups as defined herein. Examples of C1-C6-dialkylamino groups 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.

[0180] As used herein, the term "C3-C 12 -Carbocyclyl" refers to a saturated or partially unsaturated hydrocarbon ring system in which all ring members (which may be 3 to 12) are carbon atoms. The ring system may be monocyclic or polycyclic (fused, spiro or bridged). C3-C 12 -Carbocyclic groups include but are not limited to C3-C 12 -cycloalkyl (monocyclic or bicyclic), C3-C 12 -cycloalkenyl (monocyclic or bicyclic), a bicyclic system comprising an aryl group (such as phenyl) fused to a monocyclic C3-C8-cycloalkyl group (such as tetrahydronaphthyl, indanyl, 3-bicyclo[4.2.0]octa-1,3,5-triene), a bicyclic system comprising an aryl group (such as phenyl) fused to a monocyclic C3-C8-cycloalkenyl group (such as indenyl, dihydronaphthyl), and a tricyclic system comprising a cyclopropyl group connected to the bicyclic system via one carbon atom, the bicyclic system comprising an aryl group (such as phenyl) fused to a C3-C8-cycloalkyl group or a C3-C8-cycloalkenyl group. The C3-C8-cycloalkenyl group12 The -carbocycle can be attached to the parent molecular moiety through any carbon atom.

[0181] As used herein, the term "C3-C 12 "-cycloalkenyl" refers to a monovalent, monocyclic or bicyclic unsaturated hydrocarbon ring containing 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms and 1 or 2 double bonds. Examples of monocyclic C3-C8-cycloalkenyl groups include, but are not limited to, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl. Bicyclic C6-C 12 Examples of -cycloalkenyl include, but are not limited to, 3-bicyclo[4.2.0]octa-1,3,5-triene, bicyclo[2.2.1]hept-2-enyl, or bicyclo[2.2.2]oct-2-enyl.

[0182] As used herein, the term "C6-C 14 "-Aryl" refers to an aromatic hydrocarbon ring system in which all ring members (which may be 6 to 14, preferably 6 to 10) are carbon atoms. The ring system may be a monocyclic ring or a fused polycyclic ring (such as a bicyclic or tricyclic ring). Examples of aryl groups include, but are not limited to, phenyl, azulenyl, and naphthyl.

[0183] As used herein, the term "3- to 14-membered heterocyclyl" refers to a 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13-, or 14-membered saturated or partially unsaturated ring system containing 1 to 4 heteroatoms independently selected from oxygen, nitrogen, and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent. Heterocycles include, but are not limited to, 3- to 7-membered monocyclic heterocycles and 8- to 14-membered polycyclic (such as bicyclic or tricyclic) heterocycles. The 3- to 14-membered heterocycle 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 and aziridinyl; 4-membered rings, such as azetidinyl, oxetanyl, and thietanyl; 5-membered rings, such as tetrahydrofuranyl, 1,3-dioxolane, tetrahydrothiophenyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, and thiadiazolidine. alkyl; 6-membered rings such as piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothiopyranyl, dithianyl, morpholinyl, 1,2-oxazacyclohexanyl, oxathianyl, thiomorpholinyl; or 7-membered rings such as oxepanyl, azepanyl, 1,4-diazepanyl and 1,4-oxazepanyl. Examples of unsaturated heterocyclic groups include, but are not limited to, 5-membered rings such as dihydrofuranyl, 1,3-dioxolyl, dihydrothiophenyl, pyrrolinyl, dihydroimidazolyl, dihydropyrazolyl, isoxazolinyl, dihydrooxazolyl, dihydrothiazolyl; or 6-membered rings such as pyranyl, thiopyranyl, thiazinyl and thiadiazinyl. Bicyclic heterocycle can be composed of a monocyclic heteroaryl as defined herein fused to a monocyclic C3-C8-cycloalkyl, a monocyclic C3-C8-cycloalkenyl or a monocyclic heterocycle, or can be composed of a monocyclic heterocycle fused to an aryl (such as phenyl), a C3-C8-cycloalkyl, a C3-C8-cycloalkenyl or a monocyclic heterocycle. When two monocyclic heterocycles or a monocyclic heterocycle and a monocyclic heteroaryl containing a nitrogen atom are fused, the nitrogen atom can be located at the bridge (e.g., 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridyl, 5,6,7,8-tetrahydroimidazo[1,2-a]pyridyl). Tricyclic heterocycle can be composed of a monocyclic aryl ring connected to a bicyclic heterocycle by a common atom.

[0184] As used herein, the terms "3- to 7-membered heterocyclyl" and "3- to 7-membered heterocyclyl-ring" refer to a saturated ring system of 3, 4, 5, 6 or 7 members containing 1, 2 or 3 heteroatoms independently selected from oxygen, nitrogen and sulfur. Examples include, but are not limited to, oxiranyl, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothiophenyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazacyclohexaninyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothiopyranyl, dithianyl, morpholinyl, 1,2-oxazepanyl, oxathianyl, thiomorpholinyl, oxepanyl, azepanyl, 1,4-diazepanyl, and 1,4-oxazepanyl. Preferred 3- to 7-membered heterocyclic groups are oxirane, azirane, azetidinyl, oxetanyl, tetrahydrofuranyl, 1,3-dioxolanyl, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxanyl, morpholinyl and thiomorpholinyl.

[0185] As used herein, the term "5- to 14-membered heteroaryl" refers to an aromatic ring system containing 1 to 4 heteroatoms independently selected from oxygen, nitrogen, and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent. Aromatic heterocycles include 5- or 6-membered monocyclic heteroaryls and 7- to 14-membered polycyclic (e.g., bicyclic or tricyclic) heteroaryls. The 5- to 14-membered heteroaryl group can be attached to the parent molecular moiety through any carbon atom or nitrogen atom contained in the heterocycle.

[0186] As used herein, the term "5- or 6-membered heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring system comprising 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, 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, and tetrazinyl.

[0187] 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 (e.g., bicyclic or tricyclic) ring system containing 1, 2, or 3 heteroatoms independently selected from oxygen, nitrogen, and sulfur. A bicyclic heteroaryl may consist of a monocyclic heteroaryl as defined herein fused to an aryl (e.g., phenyl) or monocyclic heteroaryl. Examples of bicyclic heteroaryl groups include, but are not limited to, 9-membered rings such as indolyl, indolizinyl, isoindolyl, benzimidazolyl, imidazopyridinyl, indazolyl, benzotriazolyl, purinyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, and benzisoxazolyl, or 10-membered rings such as quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, pteridinyl, and benzodioxinyl. In a 9- or 10-membered bicyclic heteroaryl group comprising two fused 5- or 6-membered monocyclic heteroaryl groups, the nitrogen atom may be located at the bridge (e.g., imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl). Examples of tricyclic aromatic heterocyclic groups include, but are not limited to, carbazolyl, acridinyl, and phenazinyl.

[0188] As used herein, the term "C3-C 12 -Carbocyclyloxy", "C3-C8-cycloalkoxy", "C6-C 14 -aryloxy", "5- to 14-membered heteroaryloxy", "3- to 14-membered heterocyclyloxy" refer to radicals of the formula -OR, wherein R is C3-C 12 -Carbocyclic, C3-C8-cycloalkyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 14-membered heterocyclyl.

[0189] As used herein, the term "C3-C 12 -Carbocyclic sulfanyl", "C6-C 14 -arylsulfanyl, "5- to 14-membered heteroarylsulfanyl", "3- to 14-membered heterocyclylsulfanyl" refer to radicals of the formula -SR, wherein R is C3-C 12 -Carbocyclic group 、 C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 14-membered heterocyclic group.

[0190] As used herein, the term "C3-C 12 -Carbocyclic sulfinyl", "C6-C 14-arylsulfinyl", "5- to 14-membered heteroarylsulfinyl", "3- to 14-membered heterocyclylsulfinyl" refer to groups of the formula -(S=O)-R, wherein R is C3-C 12 -Carbocyclic, C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 14-membered heterocyclic group.

[0191] As used herein, the term "C3-C 12 -Carbocyclic sulfonyl", "C6-C 14 -arylsulfonyl", "5- to 14-membered heteroarylsulfonyl", "3- to 14-membered heterocyclylsulfonyl" refer to radicals of the formula -(S=O)2-R, wherein R is C3-C 12 -Carbocyclic, C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 14-membered heterocyclic group.

[0192] As used herein, the term "leaving group" is understood to mean a group that is removed from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulfonate ("triflate") group, an alkoxy group, a mesylate or p-toluenesulfonate group.

[0193] When it comes to variables m, p, Q, A 1 、A 2 , T, R 1 、R 2A , R2, R 3 、R 4 、R 5 、R 6 、R 7 、R 8 , Y and L, the term "as described herein" incorporates by reference the broad definition of the corresponding variables as well as preferred, more preferred and even more preferred definitions, if any.

[0194] Compounds obtained from combinations that contradict the laws of nature and which a person skilled in the art would therefore exclude based on his / her expert knowledge are not encompassed herein. For example, ring structures with three or more adjacent oxygen atoms are excluded.

[0195] The compound of formula (I) may suitably be in free form, salt form, N-oxide form or solvate form (eg hydrate).

[0196] 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. Therefore, the present invention covers pure stereoisomers and any mixtures of these isomers. When a compound can exist in equilibrium in two or more tautomeric forms, a reference to a compound by means of a tautomeric description should be considered to include all tautomeric forms.

[0197] 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 bonds or rings, geometric isomers may exist in cis (=Z-) or trans (=E-) form. Therefore, the present invention also relates to all geometric isomers and all possible mixtures in all proportions.

[0198] Depending on the nature of the substituents, the compounds of the formula (I) can be present in the form of free compounds and / or their salts (eg agrochemically active salts).

[0199] Agrochemically active salts include acid addition salts of inorganic and organic acids and salts of conventional bases. Examples of inorganic acids are hydrohalic acids (such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid), sulfuric acid, phosphoric acid and nitric acid, and acid salts (such as sodium hydrogen sulfate and potassium hydrogen sulfate). Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acid (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 monounsaturated or diunsaturated fatty acids having 6 to 20 carbon atoms, alkyl sulfate monoesters, alkylsulfonic acids (sulfonic acids having a linear or branched alkyl group having 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic groups such as phenyl and naphthyl with one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having a linear or branched alkyl group having 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic groups such as phenyl and naphthyl with one or two phosphonic acid groups), where the alkyl and aryl groups may have other substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

[0200] A solvate of the compound of the present invention or a salt thereof is a stoichiometric composition of the compound and a solvent.

[0201] The compounds of the present invention may exist in a variety of crystalline and / or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates and hydrates.

[0202] Preferably, the present invention relates to compounds of formula (I) and salts, hydrates and hydrates of salts thereof, wherein

[0203] A1 N or CR 8 ,

[0204] A 2 For O, S, C(=O), S(=O), S(=O)2, NR 1 or CR 2A R R2B ,

[0205] in

[0206] R 1 、R 2A and R 2B are independently hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl, wherein C1-C4-alkyl is optionally substituted by 1 to 3 groups independently selected from halogen, cyano, amino, nitro, hydroxy, formyl, carbonyl, C1-C6-alkoxy, C1-C6-

[0207] Substituted by haloalkoxy, C1-C6-alkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halogenated cycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclic groups,

[0208] and

[0209] wherein C3-C6-cycloalkyl is optionally substituted by 1 to 3 groups independently selected from halogen, cyano, nitro, hydroxy, formyl, oxo, methylene, C1-C6-alkyl,

[0210] C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C 6- substituted with a substituent selected from alkenyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -O-Si(C1-C6-alkyl)3 and 3- to 7-membered heterocyclyl, m is 0, 1 or 2,

[0211] R 3 and R 4 are independently hydrogen, fluorine, chlorine, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkyne

[0212] or C3-C6-cycloalkyl,

[0213] Among them, C1-C4-alkyl, C2-C4-alkenyl and C2-C 4- Alkynyl is optionally substituted with 1 to 3 substituents independently selected from fluoro, chloro, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl,

[0214] and

[0215] wherein the C3-C6-cycloalkyl group is optionally substituted by 1 to 3 groups independently selected from fluorine, chlorine, hydroxy, oxo, methylene, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- Alkenyl, C3-C6-cycloalkyl and C3-C6-halogenated ring

[0216] Alkyl substituents are substituted,

[0217] R 5 is hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylsulfanyl,

[0218] wherein C1-C4-alkyl, C1-C4-alkoxy and C1-C6-alkylsulfanyl are optionally substituted by 1 to 3 substituents independently selected from fluoro, chlorohydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl,

[0219] and

[0220] wherein the C3-C6-cycloalkyl group is optionally substituted by 1 to 3 groups independently selected from fluorine, chlorine, hydroxy, oxo, methylene, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- Alkenyl, C3-C6-cycloalkyl and C3-C6-halogenated ring

[0221] The alkyl group is substituted with a substituent, or

[0222] R 3 and R 5 or R 4 and R 5 Together with the carbon atoms to which they are attached, they form C3-C6-cycloalkanes

[0223] base-ring,

[0224] T is hydrogen or C1-C4-alkyl,

[0225] L is a direct bond, a C1-C6-alkylene group or a group of the formula

[0226]

[0227] in

[0228] The C1-C6-alkylene group is optionally substituted by 1 to 3 substituents L SA replace,

[0229] # is the point of connection with the heterocyclic moiety,

[0230] ##For R 6The connection point,

[0231] L 1 is a direct bond or a C1-C6-alkylene group,

[0232] L 2 is a direct bond or a C1-C6-alkylene group,

[0233] E is a C3-C6-cycloalkyl group or a 3- to 7-membered heterocyclic group,

[0234] wherein the C3-C6-cycloalkyl and 3- to 7-membered heterocyclyl groups are in turn optionally substituted by 1 to 3 substituents L SC replace,

[0235] L SA are independently fluorine, chlorine, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl,

[0236] or

[0237] Two substituents L attached to the same carbon atom SA together with the carbon atoms to which they are attached form a C3-C6 cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,

[0238] L SC are independently fluorine, chlorine, hydroxy, oxo, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- alkenyl, C3-C6-cycloalkyl or C3-C6-halocycloalkyl,

[0239] R 6 C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclic, 5- to 14-membered

[0240] Heteroaryl, C3-C 12 -Carbocyclyloxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C3-C 12 -Carbocyclylsulfanyl, C6-C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C1-C3-alkoxy, C1-C3-haloalkoxy,

[0241] Wherein C1-C3-alkoxy and C1-C3-haloalkoxy are selected from C3-C 12 -Carbocyclic, C6-C 14-aryl, 3- to 14-membered heterocyclic and 5- to 14-membered heteroaryl substituents,

[0242] wherein the C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl, in turn, are optionally substituted by 1 to 3 R 6S Substituents, where C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C 12 -Carbocyclyloxy, C6-C 14- Aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C3-C 12 -Carbocyclylsulfanyl, C6-C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl and 3- to 14-membered heterocyclylsulfanyl are optionally substituted with 1 to 3 R 6S Substituent substitution,

[0243] in

[0244] R 6S independently selected from halogen, cyano, nitro, hydroxy, mercapto, pentafluorosulfanyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C6-cycloalkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C6- 14 -aryl, 5- to 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -C(=O)(OR 17 ) and -C(=O)N(R 18 )2,

[0245] Among them C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy,

[0246] C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-

[0247] Alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl and C1-C6-haloalkylsulfanyl are in turn optionally substituted by 1 to 3 groups independently selected from hydroxy,

[0248] Substituted by C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl substituents,

[0249] and

[0250] Among them, C3-C6-cycloalkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5- to 6-membered heteroaryl and 3- to 7-membered heterocyclyl are in turn optionally substituted by 1 to 3 independently selected from fluorine, chlorine, C1-C4-

[0251] substituted by alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy substituents,

[0252] And among them

[0253] R 17 and R 18 are independently hydrogen, C1-C4-alkyl or C1-C 4- haloalkyl,

[0254] wherein the C1-C4-alkyl and C1-C 4- The haloalkyl group is optionally substituted by 1 to 3 groups independently selected from hydroxy, C1-C 4- Alkoxy,

[0255] C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C 6- The substituent of the halocycloalkyl group is substituted,

[0256] Ring Y together with the pyridine ring or the pyridazine ring respectively forms a group of formula (II-a) to (II-v),

[0257]

[0258]

[0259] in

[0260] * is the connection point with the group -OQ,

[0261] # is the connection point with another heterocycle,

[0262] p is 0, 1, 2, 3, or 4,

[0263] x 1 is 1 or 2,

[0264] x 2 is 0, 1, or 2,

[0265] R 7A 、R 7B、R 7C 、R 7D 、R 7E 、R 7F and R 7G are independently hydrogen, hydroxy, halogen, C1-C4-alkyl, C1-C 4- haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy,

[0266] R 7H is hydrogen, C1-C4-alkyl or C1-C 4- haloalkyl,

[0267] R 7K is methylene, halomethylene, halogen, hydroxy, oxo, C1-C4-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl,

[0268] or

[0269] Two substituents R 7K together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0270] R 8 is hydrogen or halogen,

[0271] Q is phenyl, naphthyl, C3-C 10 -carbocyclyl, 5- to 10-membered heterocyclyl or 5- to 10-membered

[0272] heteroaryl,

[0273] Among them, phenyl, naphthyl, C3-C 10 -Carbocyclyl, 5- to 10-membered heterocyclyl and 5- to 10-membered heteroaryl are optionally substituted by 1 to 3 Q S Substituent substitution,

[0274] in

[0275] Q S independently selected from halogen, cyano, nitro, formyl, carbonyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C 4- Alkenyl, C2-C 4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl,

[0276] 3- to 7-membered heterocyclic group, phenyl group, 5- to 6-membered heteroaryl group,

[0277] in

[0278] The C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl,

[0279] C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C 4-

[0280] Alkenyl, C2-C 4- Haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl,

[0281] C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl and C1-C4-haloalkylsulfonyl are optionally substituted by 1 to 3 groups independently selected from cyano, amino, nitro, hydroxy, C1-C4-alkoxy, C1-C4-

[0282] substituted by haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and 3- to 7-membered heterocyclyl,

[0283] The C3-C6 cycloalkyl, 3- to 7-membered heterocyclic group, phenyl and 5- or 6-

[0284] The membered heteroaryl group is in turn optionally substituted by 1 to 3 independently selected from fluorine, chlorine, C1-C4-

[0285] The alkyl radicals are substituted by substituents selected from the group consisting of C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl and C3-C6-cycloalkyl.

[0286] More preferably, the present invention relates to compounds of formula (I) and salts, hydrates and hydrates of said salts, wherein

[0287] A 2 O, NR 1 or CR 2A R R2B ,

[0288] in

[0289] R 1 、R 2A and R 2Bare independently hydrogen or C1-C4-alkyl,

[0290] m is 0 or 1,

[0291] T is hydrogen,

[0292] R 3 and R 4 are independently hydrogen, fluorine or C1-C4-alkyl,

[0293] R 5 For hydrogen,

[0294] L is a direct bond, methylene, monofluoromethylene or difluoromethylene,

[0295] R 6 is indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl or dihydrobenzodioxanyl,

[0296] wherein indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl and dihydrobenzodioxanyl are optionally substituted by one or two R 6S Substituent substitution,

[0297] in

[0298] R 6S are independently selected from fluorine, chlorine, bromine, C1-C4-alkyl, difluoromethyl, trifluoromethyl,

[0299] C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, methylcarbonyl, ethylcarbonyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridyl,

[0300] wherein cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridyl are in turn optionally substituted by 1 to 3 groups independently selected from fluorine, chlorine, C1-C4-

[0301] substituted by alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy substituents,

[0302] A 1 N or CR 8 ,

[0303] in

[0304] R 8 For hydrogen,

[0305] Q is phenyl, optionally substituted by one or two substituents Q S replace,

[0306] in

[0307] Q S independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-

[0308] Haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- alkenyl, C2-C4-alkynyl, cyclopropyl and cyclobutyl,

[0309] wherein the cyclopropyl and cyclobutyl are in turn optionally substituted with one or two substituents independently selected from fluoro or methyl,

[0310] and

[0311] Ring Y forms together with the pyridine ring or the pyridazine ring a radical of the formula (II-a), (II-b), (II-g), (II-h), (II-r), (II-s), (II-u) or (II-v),

[0312]

[0313]

[0314] in

[0315] * is the connection point with the group -OQ,

[0316] # is the connection point with another heterocycle,

[0317] p is 0, 1, or 2,

[0318] x 1 is 1 or 2,

[0319] x 2 is 0, 1, or 2,

[0320] R 7A is hydrogen or C1-C4-alkyl,

[0321] R 7B is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy,

[0322] R 7C is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy,

[0323] R 7D For hydrogen,

[0324] R 7E For hydrogen,

[0325] R 7F For hydrogen,

[0326] R 7K is hydroxy, C1-C4-alkyl or C1-C4-alkoxy.

[0327] Even more preferably, the present invention relates to compounds of formula (I) and salts, hydrates and hydrates of said salts thereof, wherein

[0328] A 2 O, NR 1 or CR 2A R R2B ,

[0329] in

[0330] R 1 、R 2A and R 2B are independently hydrogen or C1-C4-alkyl,

[0331] m is 0 or 1,

[0332] T is hydrogen,

[0333] R 3 and R 4 are independently hydrogen, fluorine or C1-C4-alkyl,

[0334] R 5 For hydrogen,

[0335] L is a direct bond, methylene, monofluoromethylene or difluoromethylene,

[0336] R 6 is indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl or dihydrobenzodioxanyl,

[0337] wherein indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl and dihydrobenzodioxanyl are optionally substituted by one or two R 6S Substituent substitution,

[0338] in

[0339] R 6S are independently selected from fluorine, chlorine, bromine, C1-C4-alkyl, difluoromethyl, trifluoromethyl,

[0340] C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, methylcarbonyl, ethylcarbonyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridyl,

[0341] wherein cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridyl are in turn optionally substituted by 1 to 3 groups independently selected from fluorine, chlorine, C1-C4-

[0342] Alkyl, C1-C 4- Haloalkyl, C1-C4-alkoxy and C1-C 4- The substituent of the haloalkoxy group is substituted,

[0343] A 1 N or CR 8 ,

[0344] in

[0345] R 8 For hydrogen,

[0346] Q is phenyl, optionally substituted by one or two substituents Q S replace,

[0347] in

[0348] Q S independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-

[0349] haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, cyclopropyl and cyclobutyl,

[0350] wherein the cyclopropyl and cyclobutyl are in turn optionally substituted with one or two substituents independently selected from fluoro or methyl,

[0351] and

[0352] Ring Y forms together with the pyridine ring or pyridazine ring a radical of the formula (II-a), (II-g), (II-h) or (II-r),

[0353]

[0354] or

[0355]

[0356] in

[0357] * is the connection point with the group -OQ,

[0358] # is the connection point with another heterocycle,

[0359] p is 0 or 1,

[0360] x 1 is 1 or 2,

[0361] R 7A For hydrogen,

[0362] R 7B is hydrogen or C1-C4-alkyl,

[0363] R 7C For hydrogen,

[0364] R 7D For hydrogen,

[0365] R 7E For hydrogen,

[0366] R 7F For hydrogen,

[0367] R 7K It is C1-C4-alkyl.

[0368] A 1 Preferably N or CR 8 , where R 8 is hydrogen, fluorine, chlorine or bromine. Most preferably, A 1 It is N or CH.

[0369] A 2 Preferably O, S, C(=O), S(=O)2, NR 1 or CR 2A R 2B , where R 1 、R 2A and R 2B are independently hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl or cyclobutyl.

[0370] More preferably, A 2 O, NR 1 or CR 2A R 2B , where R 1 、R 2A and R 2B are independently hydrogen, methyl, ethyl, cyclopropyl or cyclobutyl. Most preferably, A 2 is O, NH or CH2.

[0371] m is preferably 0 or 1, more preferably 1.

[0372] T is preferably hydrogen or C1-C4 alkyl, more preferably hydrogen, methyl, ethyl, n-propyl or isopropyl, most preferably hydrogen.

[0373] R 3 and R 4 Preferably, they are independently selected from hydrogen, fluorine, chlorine, C1-C4-alkyl, C2-C4-alkenyl, C2-C4- Alkynyl and C3-C6-cycloalkyl,

[0374] Among them, C1-C4-alkyl, C2-C4-alkenyl and C2-C 4- Alkynyl is optionally substituted by 1 to 3 groups independently selected from fluoro, chloro, hydroxy, C1-C4-alkoxy, C1-C 4- Substituted by haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl substituents,

[0375] and

[0376] wherein C3-C6-cycloalkyl is optionally substituted by 1 to 3 groups independently selected from fluoro, chloro, hydroxy, oxo, methylene, C1-C4-alkyl, C1-C 4- Halogenated alkyl, C1-C4-alkoxy, C1-C 4- Halogenated alkoxy, C2-C 4- Substituted by alkenyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl substituents,

[0377] or R 3 and R 4 Together with the carbon atom to which they are attached they form a C3-C6-cycloalkyl-ring.

[0378] More preferably, R 3 and R 4 independently selected from hydrogen, fluorine, chlorine, C1-C4-alkyl, C2-C4-alkenyl, C2-C 4- Alkynyl and C3-C6-cycloalkyl are even more preferably selected from hydrogen, fluorine and C1-C4-alkyl, even more preferably selected from hydrogen, fluorine, methyl, ethyl, n-propyl and isopropyl.

[0379] Most preferably, R 3 and R 4 All are hydrogen.

[0380] R 5 Preferably, hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylsulfanyl, wherein C1-C4-alkyl, C1-C4-alkoxy and C1-C6-alkylsulfanyl are optionally substituted by 1 to 3 groups independently selected from fluorine, chlorine, hydroxy, C1-C4-alkoxy, C1-C 4- Substituted by haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl substituents,

[0381] and

[0382] wherein C3-C6-cycloalkyl is optionally substituted by 1 to 3 groups independently selected from fluoro, chloro, hydroxy, oxo, methylene, C1-C4-alkyl, C1-C 4-Haloalkyl, C1-C4-alkoxy, C1-C 4- Substituted by haloalkoxy, C2-C4-alkenyl, C3-C6-cycloalkyl and C3-C6-halocycloalkyl substituents,

[0383] or

[0384] R 3 and R 5 or R 4 and R 5 Together with the carbon atom to which they are attached they form a C3-C6-cycloalkyl-ring.

[0385] R 5 More preferably it is hydrogen, hydroxy, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylsulfanyl, even more preferably it is hydrogen, hydroxy or C1-C4-alkyl, even more preferably it is hydrogen, methyl, ethyl, n-propyl or isopropyl, most preferably hydrogen.

[0386] More preferably, A 2 is O, NH or CH2, m is 0 or 1, T is hydrogen, R 3 、R 4 and R 5 Each is hydrogen.

[0387] L is preferably a direct bond, a C1-C6-alkylene group or a group of the formula

[0388]

[0389] in

[0390] The C1-C6-alkylene group is optionally substituted by 1 to 3 substituents L SA replace,

[0391] # is the point of connection to the heterocyclyl-part,

[0392] ##For R 6 The connection point,

[0393] L 1 is a direct bond or a C1-C6-alkylene group,

[0394] L 2 is a direct bond or a C1-C6-alkylene group,

[0395] E is a C3-C6-cycloalkyl group or a 3- to 7-membered heterocyclic group,

[0396] wherein the C3-C6-cycloalkyl and 3- to 7-membered heterocyclyl groups are in turn optionally substituted by 1 to 3 substituents L SC replace,

[0397] L SAare independently fluorine, chlorine, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl,

[0398] or

[0399] Two substituents L bonded to the same carbon atom SA together with the carbon atoms to which they are attached form a C3-C6 cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,

[0400] L SC are independently fluoro, chloro, hydroxy, oxo, C1-C4-alkyl, C1-C 4- Halogenated alkyl, C1-C4-alkoxy, C1-C 4- Haloalkoxy, C2-C4-alkenyl, C3-C6-cycloalkyl or C3-C 6- Halogenated cycloalkyl.

[0401] L is more preferably a direct bond or a C1-C6-alkylene group, wherein the C1-C6-alkylene group is optionally substituted by 1 to 3 substituents L SA Substituted, where L SA are independently fluorine, chlorine, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl.

[0402] Even more preferably, L is a direct bond or a C1-C4-alkylene group, wherein said C1-C4-alkylene group is optionally substituted by one or two substituents L SA Substituted, where L SA are independently fluoro or chloro.

[0403] L is even more preferably a direct bond, methylene, ethylene, propyl-1,3-ylidene, propyl-1,2-ylidene, butyl-1,4-ylidene, butyl-1,3-ylidene, butyl-1,2-ylidene, monofluoromethylene or difluoromethylene, even more preferably a direct bond, methylene, monofluoromethylene or difluoromethylene, most preferably methylene.

[0404] R 6 Preferably C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C 12 -Carbocyclyloxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C3-C 12 -Carbocyclylsulfanyl, C6-C 14- arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C1-C3-alkoxy or C1-C3-haloalkoxy,

[0405] Among them, C1-C3-alkoxy and C1-C 3- The haloalkoxy group is replaced by a group selected from C3-C 12 -Carbocyclic, C6-C 14 -substituted with a substituent of an aryl group, a 3- to 14-membered heterocyclic group, and a 5- to 14-membered heteroaryl group,

[0406] wherein the C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl, which in turn are optionally substituted by 1 to 3 R 6S Substituents, where C3-C 12 -Carbocyclic, C6-C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C 12 -Carbocyclyloxy, C6-C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C3-C 12 -Carbocyclylsulfanyl, C6-C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl and 3- to 14-membered heterocyclylsulfanyl are optionally substituted with 1 to 3 R 6S Substituent substitution,

[0407] in

[0408] R 6S independently selected from halogen, cyano, nitro, hydroxy, mercapto, pentafluorosulfanyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl,

[0409] C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl,

[0410] C1-C6-haloalkylsulfanyl, C3-C6-cycloalkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5- to 6-membered heteroaryl, 3-

[0411] to 7-membered heterocyclic group, -C(=O)(OR 17 ) and -C(=O)N(R 18 )2,

[0412] Among them, C1-C6-alkyl, C1-C 6- Halogenated alkyl, C1-C6-alkoxy, C1-C 6-

[0413] Halogenated alkoxy, C2-C6-alkenyl, C2-C 6- Halogenated alkenyl, C2-C 6- Alkynyl,

[0414] C2-C 6- Haloalkynyl, C1-C6-alkylsulfanyl and C1-C 6- The haloalkylsulfanyl group is in turn optionally substituted by 1 to 3 groups independently selected from hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C6 cycloalkyl and C3-C6 halo-

[0415] Substituents of the cycloalkyl group are substituted,

[0416] and

[0417] Among them, C3-C6-cycloalkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are in turn optionally substituted by 1 to 3 independently selected from fluorine, chlorine, C1-C4-

[0418] Alkyl, C1-C 4- Substituents of haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy,

[0419] And among them

[0420] R 17 and R 18 are independently hydrogen, C1-C4-alkyl or C1-C 4- haloalkyl,

[0421] wherein the C1-C4-alkyl and C1-C4-haloalkyl groups are optionally replaced by 1 to 3 groups independently selected from hydroxy, C1-C 4- Alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C 6- The substituents of the halocycloalkyl group are substituted.

[0422] More preferably, R 6The following are indanyl, 1,2,3,4-tetrahydronaphthyl, bicyclo[4.2.0]octa-1,3,5-trienyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indenyl, 1,2-dihydronaphthyl, spiro[cyclopropane-2,1'-dihydroindane]-1-yl, spiro[cyclopropane-2,1'-tetrahydronaphthyl]-1-yl, phenyl, naphthyl, phenoxy, benzyloxy, OCF2-phenyl, phenylsulfanyl, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothiophenyl, dihydroindole, 1,3-benzodioxolanyl, 1,2,3,4-tetrahydroquinolinyl, dihydrobenzopyranyl, isodihydrobenzopyranyl, thiodihydrobenzopyranyl, pyranyl, 2,3-dihydro-1,4-benzodioxane, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, 5,6,7,8-tetrahydroquinolinyl, 4,5,6,7-tetrahydrobenzothiophenyl, 4,5,6,7-tetrahydrobenzofuranyl, 4,5,6,7-tetrahydro-1,3-benzoxazolyl, 4,5,6,7-tetrahydro-1,3-benzothiazolyl, 4,5,6,7-tetrahydro-1H-benzimidazolyl, 4,5,6,7-tetrahydro-1H-indazolyl, 4,5,6,7-tetrahydro-1H-isoindolyl, 4,5,6,7-tetrahydro-2-benzothiophenyl, 5,6-dihydro-4H-cyclopenta[b]pyridinyl, ]thienyl, 5,6-dihydro-4H-cyclopenta[d]thiazolyl, 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, 6,7-dihydro-5H-thieno[3,2-b]pyranyl, spiro[dihydrochromen-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinolin-6,1'-cyclopropane]-yl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidine yl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, pyrrolo[2,3-b]pyridin-3-yl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[3,2-b]pyrrol-6-yl, thieno[3,2-b]thienyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl or thieno[2,3-d]isothiazolyl, among which indanyl, 1,2,3,4-tetrahydronaphthyl, bicyclo[4.2.0]octa-1,3,5-triene, bicyclo[4.2.0] octa-1(6),2,4-triene, indenyl, 1,2-dihydronaphthyl, spiro[cyclopropane-2,1'-dihydroindane]-1-yl, spiro[cyclopropane-2,1'-tetrahydronaphthalene]-1-yl, phenyl, naphthyl, phenoxy, benzyloxy, OCF2-phenyl, phenylsulfanyl, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothiophenyl, dihydroindole, 1,3-benzodioxolane, 1,2,3,4-tetrahydroquinolinyl, dihydrobenzopyranyl, isodihydrobenzopyranyl, thiodihydrobenzopyranyl, 2,3-dihydro-1,4-benzodioxane, 6,7 -dihydro-5H-cyclopenta[b]pyridinyl, 5,6,7,8-tetrahydroquinolinyl, 4,5,6,7-tetrahydrobenzothiophenyl, 4,5,6,7-tetrahydrobenzofuranyl, 4,5,6,7-tetrahydro-1,3-benzoxazolyl, 4,5,6,7-tetrahydro-1,3-benzothiazolyl, 4,5,6,7-tetrahydro-1H-benzimidazolyl, 4,5,6,7-tetrahydro-1H-indazolyl, 4,5,6,7-tetrahydro-2H-isoindolyl, 4,5,6,7-tetrahydro-2-benzothiophenyl, 5,6-dihydro-4H-cyclopenta[b]thiophenyl, 5,6 -dihydro-4H-cyclopenta[d]thiazolyl, 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, 6,7-dihydro-5H-thieno[3,2-b]pyranyl, spiro[dihydrochromen-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinolin-6,1'-cyclopropane]-yl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl , pyridyl, pyridazinyl and pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[2,3-b]pyridin-3-yl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[3,2-b]pyrrol-6-yl, thieno[3,2-b]thienyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl and thieno[2,3-d]isothiazolyl, and optionally substituted by 1 to 3 substituents R. 6S Replace, where

[0423] R 6Sindependently selected from halogen, cyano, nitro, hydroxy, mercapto, pentafluorosulfanyl, oxo, methylene, halomethylene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C6-cycloalkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C6- 14 -aryl, 5- to 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -C(=O)(OR 17 )

[0424] and -C(=O)N(R 18 ) 2, wherein C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl and C1-C6-haloalkylsulfanyl are further optionally substituted with 1 to 3 substituents independently selected from fluorine, chlorine, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl, and wherein C3-C6-cycloalkylsulfanyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C6-C 14 -aryl, 5- to 6-membered heteroaryl and 3- to 7-membered heterocyclyl are further optionally substituted by 1 to 3 substituents independently selected from fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy,

[0425] in

[0426] R 17 and R 18 are independently hydrogen or C1-C4-alkyl,

[0427] wherein said C1-C4-alkyl or C1-C4-haloalkyl is in turn optionally substituted by 1 to 3 substituents independently selected from fluorine, chlorine, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl and C3-C6-halocycloalkyl.

[0428] Even more preferably, R 6 is indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl or dihydrobenzodioxanyl, wherein indanyl, 1,2,3,4-tetrahydronaphthyl, phenyl, naphthyl, dihydrobenzofuranyl and dihydrobenzodioxanyl are optionally substituted by one or two R6S Substituents are substituted, wherein

[0429] R 6S independently selected from fluorine, chlorine, bromine, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, methylcarbonyl, ethylcarbonyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridyl,

[0430] wherein cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridyl are in turn optionally substituted by 1 to 3 groups independently selected from fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4- 4- The substituents of the haloalkoxy group are substituted.

[0431] Even more preferably, R 6 for

[0432]

[0433] in

[0434] § 1 is the connection point with L,

[0435] R 6S1 and R 6S2 are independently hydrogen or R 6S ,

[0436] in

[0437] R 6S is halogen, cyano, C1-C4-alkyl, C1-C 4- Halogenated alkyl, C1-C4-

[0438] Alkoxy, C1-C 6- Halogenated alkoxy, C1-C 6- Alkoxycarbonyl,

[0439] C1-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-

[0440] Cycloalkyl and pyrazolyl,

[0441] wherein said C3-C6-cycloalkyl and pyrazolyl are optionally substituted by one or two substituents independently selected from halogen and C1-C4-alkyl,

[0442] Condition R 6S1 and R 6S2 At least one of the carbon atoms is different from hydrogen.

[0443] Most preferably, R6 is phenyl, with one or two R 6S Substituent substitution,

[0444] in

[0445] R 6S independently selected from chloro, bromo, methyl, vinyl and pyrazolyl,

[0446] wherein the pyrazolyl group is further substituted by a methyl group.

[0447] More preferably, L is methylene and R 6 is phenyl, with one or two R 6S Substituent substituted, where R 6S Independently selected from chloro, bromo, methyl, vinyl and pyrazolyl, wherein said pyrazolyl is in turn substituted with a methyl substituent.

[0448] Even more preferably, A 2 is O, NH or CH2, m is 0 or 1, T is hydrogen, R 3 、R 4 and R 5 Each is hydrogen, L is methylene and R 6 is phenyl, with one or two R 6S Substituent substituted, where R 6S Independently selected from chloro, bromo, methyl, vinyl and pyrazolyl, wherein said pyrazolyl is in turn substituted with a methyl substituent.

[0449] 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-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, 3- to 7-membered heterocyclyl, -N(R 20 )2、-C(=NR 21 )R 22 、-C(=O)(OR 25 ) or -C(=O)N(R 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-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl and C1-C6-haloalkylsulfonyl are optionally substituted by 1 to 3 R 7Sa Substituents, wherein C3-C8-cycloalkyl and 3- to 7-membered heterocyclyl, optionally substituted with 1 to 3 R 7Sa Substituents, wherein C3-C8-cycloalkyl and 3- to 7-membered heterocyclyl are optionally substituted with 1 to 3 R 7Sc Substituent substitution,

[0450] in

[0451] R 20 is hydrogen, C1-C6-alkyl, C1-C 6- haloalkyl or C3-C6-cycloalkyl,

[0452] wherein C3-C8-cycloalkyl is optionally substituted by one or two substituents independently selected from halogen and C1-C6-alkyl,

[0453] R 21 is hydroxy, C1-C6-alkyl or C1-C 6- Alkoxy,

[0454] R 22 is hydrogen, C1-C6-alkyl or C1-C 6- haloalkyl,

[0455] R 25 and R 26 are independently hydrogen or C1-C6-alkyl,

[0456] And among them

[0457] R 7Sa are independently cyano, hydroxy, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl or C1-C4-alkoxycarbonyl,

[0458] R 7Sc are independently halogen, hydroxy, C1-C4-alkyl, C1-C4-haloalkyl,

[0459] C1-C4-alkoxy or C1-C4-haloalkoxy.

[0460] More preferably, 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, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, -N(R 20 )2、-C(=NR 21 )R 22 or -C(=O)(OR 25 ), wherein 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 C3-C6-cycloalkyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl is optionally substituted with one or two R 7Sc Substituent substitution,

[0461] in

[0462] R 20 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl,

[0463] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[0464] R 22 is a C1-C4-alkyl group,

[0465] R 25 is hydrogen or C1-C4-alkyl,

[0466] And among them

[0467] R 7Sa are independently C1-C4-alkoxy,

[0468] R 7Sc is independently halogen or C1-C4-alkyl.

[0469] Even more preferably, R 7 is chlorine, iodine, C1-C4-alkyl, difluoromethyl, trifluoromethyl, methylcarbonyl, ethylcarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, -N(R 20 )2 or -C(=NR 21 )R 22 ,

[0470] wherein C1-C4-alkyl, C2-C4-alkenyl and C2-C4-alkynyl are optionally substituted by one or two R 7Sa Substituent substitution,

[0471] wherein the C3-C6-cycloalkyl group is optionally replaced by one or two R 7Sc Substituent substitution,

[0472] R 20 is hydrogen, cyclopropyl or cyclobutyl,

[0473] R 21 is C1-C4-alkyl or C1-C4-alkoxy,

[0474] R 22 is a C1-C4-alkyl group,

[0475] And among them

[0476] R 7Sa are independently C1-C4-alkoxy,

[0477] R 7Sc are independently halogen.

[0478] Even more preferably, R 7 is chlorine, iodine, C1-C4-alkyl, difluoromethyl, trifluoromethyl, methylcarbonyl, ethylcarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl or pyrrolidinyl.

[0479] Even more preferably, R 7 It is methyl, ethyl, n-propyl or isopropyl, most preferably methyl.

[0480] p is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and most preferably 0 or 1.

[0481] More preferably, R 7 is methyl and p is 0 or 1.

[0482] Q is preferably phenyl, naphthyl, C3-C 10 -carbocyclyl, 5- to 10-membered heterocyclyl or 5- to 10-membered heteroaryl, wherein phenyl, naphthyl, C3-C 10 -carbocyclyl, 5- to 10-membered heterocyclyl and 5- to 10-membered heteroaryl, optionally substituted by 1 to 3 substituents Q S replace,

[0483] in

[0484] Q Sindependently selected from halogen, cyano, nitro, formyl, carbonyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C 4- Alkenyl, C2-C 4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C3-C6-cycloalkyl, 3- to 7-membered heterocyclyl, phenyl,

[0485] 5- to 6-membered heteroaryl,

[0486] in

[0487] The C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, C2-C 4- Alkenyl, C2-C 4- haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl and C1-C4-haloalkylsulfonyl are in turn optionally substituted with 1 to 3 substituents independently selected from cyano, amino, nitro, hydroxy, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and 3- to 7-membered heterocyclyl,

[0488] The C3-C6-cycloalkyl, 3- to 7-membered heterocyclyl, phenyl and 5- to 6-membered heteroaryl are in turn optionally substituted with 1 to 3 substituents independently selected from fluorine, chlorine, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl and C3-C6-cycloalkyl.

[0489] More preferably, Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-triene, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, bicyclo[4.2.0]octa-1(6),2,4-triene, dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, dihydroindolyl, 1,3-benzodioxolanyl, dihydrochromenyl, dihydro-1,4-benzodioxanyl, [1,3]dioxolo[4,5-b] pyridyl, tetrahydroquinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridyl, thieno[3,2-b]thienyl or thieno[2,3-d]thiazolyl, wherein phenyl , naphthyl, bicyclo[4.2.0]oct-1(6),2,4-triene, indanyl, tetrahydronaphthyl, indenyl, dihydronaphthyl, bicyclo[4.2.0]oct-1(6),2,4-triene, dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, dihydroindolyl, 1,3-benzodioxolane, dihydrobenzopyranyl, dihydro-1,4-benzodioxane, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinone quinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thienyl and thieno[2,3-d]thiazolyl, optionally substituted by 1 to 3 substituents Q S Replace, where

[0490] Q S 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-C 6- Alkenyl, C2-C 6- Halogenated alkenyl, C2-C6-alkynyl, C2-C6-halogenated alkynyl, C1-C6-alkylsulfanyl, C1-C6-halogenated alkylsulfanyl, C3-C6-cycloalkyl, oxetanyl and -N(R 43 ) 2, wherein the C3-C6-cycloalkyl and oxetanyl, in turn, are optionally substituted by one or two substituents independently selected from halogen, C1-C4-alkyl and C1-C4-haloalkyl, wherein R43 is hydrogen and C1-C6-alkyl.

[0491] Even more preferably, Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-triene, benzodioxolanyl, 2,3-dihydrobenzofuranyl, pyridyl, thienyl or indolyl, wherein phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-triene, benzodioxolanyl, 2,3-dihydrobenzofuranyl, pyridyl, thienyl and indolyl are optionally substituted by 1 to 3 substituents Q S Replace, where

[0492] Q S 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 and C3-C6-cycloalkyl, wherein said C3-C6-cycloalkyl is in turn optionally substituted by one or two substituents independently selected from fluoro or methyl.

[0493] Even more preferably, Q is phenyl, wherein the phenyl group is substituted by one or two groups independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C 4- Substituent Q of haloalkyl, C1-C4 alkylcarbonyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyl, C2-C4 alkynyl, cyclopropyl and cyclobutyl S Substituted, wherein the cyclopropyl and cyclobutyl are in turn optionally substituted with one or two substituents independently selected from fluoro or methyl.

[0494] Even more preferably, Q is phenyl, substituted by one or two substituents Q independently selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C4-alkenyl, C2-C4-alkynyl and cyclopropyl. S replace.

[0495] Even more preferably, Q is phenyl, substituted by one or two substituents Q independently selected from fluoro, chloro, bromo, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, vinyl, ethynyl and cyclopropyl. S replace.

[0496] Most preferably, Q is

[0497]

[0498] in

[0499] § 2 is the connection point with the oxygen atom,

[0500] Q S1 is hydrogen or fluorine,

[0501] Q S2 is hydrogen, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, vinyl, ethynyl or cyclopropyl,

[0502] Condition is Q S1 and Q S2 At least one of the carbon atoms is different from hydrogen.

[0503] More preferably, A 1 is N or CH and Q is phenyl, wherein phenyl is substituted by one or two independently selected from halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- Substituents Q of alkenyl, C2-C4-alkynyl, cyclopropyl and cyclobutyl S Substituted, wherein the cyclopropyl and cyclobutyl are in turn optionally substituted with one or two substituents independently selected from fluoro or methyl.

[0504] Even more preferably, A 1 is N or CH and Q is phenyl, substituted by one or two substituents Q independently selected from fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, vinyl, ethynyl and cyclopropyl S replace.

[0505] Even more preferably, A 2 is O, NH or CH2, m is 0 or 1, T is hydrogen, R 3 、R 4 and R 5 Each of them is hydrogen, L is methylene, R 6 is phenyl, with one or two R 6S Substituent substituted, where R 6S are independently selected from chloro, bromo, methyl, vinyl and pyrazolyl, wherein the pyrazolyl is in turn substituted with a methyl substituent, A 1 is N or CH and Q is phenyl, substituted by one or two substituents Q independently selected from fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, vinyl, ethynyl and cyclopropyl S replace.

[0506] Ring Y preferably forms together with the pyridine- or pyridazine-ring a radical of the formula (II-a), (II-b), (II-g), (II-h), (II-r), (II-s), (II-u) or (II-v)

[0507]

[0508] in

[0509] * is the connection point with the group -OQ,

[0510] # is the connection point with another heterocycle,

[0511] p is 0, 1, or 2,

[0512] x 1 is 1 or 2,

[0513] x 2 is 0, 1, or 2,

[0514] R 7A is hydrogen or C1-C4-alkyl,

[0515] R 7B is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy,

[0516] R 7C is hydrogen, fluorine, C1-C4-alkyl or C1-C4-alkoxy,

[0517] R 7D For hydrogen,

[0518] R 7E For hydrogen,

[0519] R 7F For hydrogen,

[0520] R 7K is hydroxy, C1-C4-alkyl or C1-C4-alkoxy.

[0521] More preferably, ring Y forms together with the pyridine ring or pyridazine ring a group of formula (II-a), (II-g), (II-h) or (II-r),

[0522]

[0523] in

[0524] * is the connection point with the group -OQ,

[0525] # is the connection point with another heterocycle,

[0526] p is 0 or 1, preferably 0,

[0527] x 1 is 1 or 2,

[0528] R 7A For hydrogen,

[0529] R 7Bis hydrogen or C1-C4 alkyl, preferably hydrogen, methyl, ethyl, n-propyl or isopropyl, more preferably hydrogen or methyl,

[0530] R 7C For hydrogen,

[0531] R 7D For hydrogen,

[0532] R 7E For hydrogen,

[0533] R 7F For hydrogen,

[0534] R 7K It is C1-C4-alkyl.

[0535] Even more preferably, A 2 is O, NH or CH2, m is 0 or 1, T is hydrogen, R 3 、R 4 and R 5 Each of them is hydrogen, L is methylene, R 6 is phenyl, with one or two R 6S Substituent substituted, where R 6S are independently selected from chloro, bromo, methyl, vinyl and pyrazolyl, wherein the pyrazolyl is in turn substituted with a methyl substituent, A 1 is N or CH, Q is phenyl, substituted by one or two substituents Q independently selected from fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, vinyl, ethynyl and cyclopropyl S substituted, and ring Y forms a group of formula (II-a), (II-g), (II-h) or (II-r) with the pyridine ring or the pyridazine ring, respectively,

[0536]

[0537] in

[0538] * is the connection point with the group -OQ,

[0539] # is the connection point with another heterocycle,

[0540] p is 0,

[0541] x 1 is 1 or 2,

[0542] R 7A For hydrogen,

[0543] R 7B is hydrogen or C1-C4 alkyl, preferably hydrogen, methyl, ethyl, n-propyl or isopropyl, more preferably hydrogen or methyl,

[0544] R 7C For hydrogen,

[0545] R 7D For hydrogen,

[0546] R 7E For hydrogen,

[0547] R 7F For hydrogen.

[0548] A specifically defined above 1 、A 2 、R 1 、R 2A 、R 2B 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 , L, m, p, T, Q (broad definitions and preferred, more preferred, even more preferred and most preferred definitions) can be combined in various ways. Therefore, the combination of these definitions provides a subset of the compounds of the present invention, such as those disclosed below.

[0549] Preference is given to those compounds of the formula (I) in which the individual definitions (substituents and variables) have the preferred meanings indicated above.

[0550] Particular preference is given to those compounds of the formula (I) in which the individual definitions (substituents and variables) have the abovementioned more preferred, even more preferred and / or most preferred meanings.

[0551] The present invention also relates to any compound of formula (I) disclosed in Table 1.

[0552] The most preferred compounds of formula (I) and their salts, hydrates and hydrates of said salts, wherein

[0553] A 1 is N or CH,

[0554] A 2 is O, NH or CH2,

[0555] m is 0 or 1, preferably 1,

[0556] T is hydrogen,

[0557] R 3 、R 4 and R 5 Each is hydrogen,

[0558] L is a methylene group,

[0559] R 6 is phenyl, with one or two R6S Substituent substitution,

[0560] in

[0561] R 6S independently selected from chloro, bromo, methyl, vinyl and pyrazolyl,

[0562] wherein the pyrazolyl group is substituted with a methyl substituent,

[0563] Q is phenyl, substituted by one or two groups Q S replace,

[0564] in

[0565] Q S Independently selected from fluorine, chlorine, bromine, methyl, trifluoromethyl, vinyl,

[0566] Ethynyl and cyclopropyl,

[0567] and

[0568] Ring Y forms together with the pyridine ring or pyridazine ring a radical of the formula (II-a), (II-g), (II-h) or (II-r),

[0569]

[0570] in

[0571] * is the connection point with the group -OQ,

[0572] # is the connection point with another heterocycle,

[0573] p is 0,

[0574] x 1 is 1 or 2,

[0575] R 7A For hydrogen,

[0576] R 7B is hydrogen or methyl,

[0577] R 7C For hydrogen,

[0578] R 7D For hydrogen,

[0579] R 7E For hydrogen,

[0580] R 7F For hydrogen.

[0581] The compounds of formula (I) are useful 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 plants, plant parts, seeds, fruits or soil in which the plants grow.

[0582] Processes and intermediates for preparing compounds of formula (I)

[0583] The present invention also relates to a process for preparing compounds of formula (I) and intermediates thereof. Unless otherwise indicated, the variable A used hereinafter is 1 、A 2 、R 1 、R 2A 、R 2B 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 , L, m, p, T, Q and Y have the meanings given above for compounds of formula (I). These definitions apply not only to the final products of formula (I), but also to all intermediates containing the respective variables.

[0584] The compounds of formula (Ia) are various subsets of formula (I). The compounds of formulas (Ia-1) to (Ia-3) are various subsets of formula (Ia). Unless otherwise indicated, all variables in formulas (Ia) and (Ia-1) to (Ia-3) are as defined above for formula (I).

[0585] Compounds of formula (I) can be prepared by various routes analogous to known methods. Non-limiting examples of suitable methods are described herein.

[0586] Compounds of formula (I) can be obtained directly by carrying out one of the methods A to E outlined below, or can be obtained by transformation or derivatization of another compound of formula (I) prepared according to the methods described herein. For example, a compound of formula (I) can be converted into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) with other substituents.

[0587] The methods described herein can be suitably carried out using one or more inert organic solvents, which are conventional solvents for the reaction under consideration. Suitable inert organic solvents can be selected from the following: aliphatic, alicyclic or aromatic hydrocarbons (e.g., petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, petroleum ether, benzene, toluene, xylene or decahydronaphthalene); halogenated aliphatic, alicyclic or aromatic hydrocarbons (e.g., chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane); ethers (e.g., diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-ethoxyethane or anisole); ketones (e.g., acetone, methyl ethyl ketone); , methyl isopropyl ketone and methyl isobutyl ketone); esters (for example methyl acetate, ethyl acetate or butyl acetate); alcohols (for example methanol, ethanol, propanol, isopropanol, butanol, tert-butanol); nitriles (for example acetonitrile, propionitrile, n- or isobutyronitrile or benzonitrile); amides (for example N,N-dimethylformamide, N,N-methylacetamide, N-methylformimide, N-methylpyrrolidone or hexamethylphosphoric triamide); sulfoxides (for example dimethyl sulfoxide) or sulfones (for example sulfolane); ureas (for example 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone) or any mixtures thereof.

[0588] Some of the methods described herein may require or optionally utilize one or more inorganic or organic bases commonly used in such reactions. Examples of suitable inorganic and organic bases include, but are not limited to, alkaline earth or alkali metal carbonates (e.g., sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, or cesium carbonate), alkali metal hydrides (e.g., sodium hydride), alkaline earth or alkali metal hydroxides (e.g., sodium hydroxide, calcium hydroxide, potassium hydroxide, or other ammonium hydroxide derivatives), alkaline earth, alkali, or ammonium fluorides (e.g., potassium fluoride, cesium fluoride, or tetrabutylammonium fluoride), alkali or alkaline earth metal acetates (e.g., sodium acetate, lithium acetate, potassium acetate, or calcium acetate), alkali metal alkoxides (e.g., Such as potassium tert-butoxide, sodium tert-butoxide), alkali metal phosphates (such as tripotassium phosphate), tertiary amines (such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dicyclohexylmethylamine, N,N-diisopropylethylamine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN), diazabicycloundecene (DBU), quinuclidine, 3-acetoxyquinuclidine, guanidine or aromatic bases (such as pyridine, picoline, lutidine or collidine).

[0589] Some of the methods described herein can optionally be performed in the presence of a transition metal catalyst, such as a metal (eg, copper or palladium) salt or complex, and if appropriate, in the presence of a ligand.

[0590] Suitable copper salts or complexes and hydrates thereof 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) thiophene-2-carboxylate, copper (I) cyanide, copper (II) sulfate, copper (II) bis(2,2,6,6-tetramethyl-3,5-heptanedione)ate, copper (II) trifluoromethanesulfonate, copper (I) tetrakis(acetonitrile)hexafluorophosphate, and copper (I) tetrakis(acetonitrile)tetrafluoroborate.

[0591] Suitable copper complexes can also be generated in situ in the reaction mixture by separately adding a copper salt and a ligand or salt to the reaction, such as 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-di(2-pyridyl)pyridine, 2-picolinic acid, 2-(dimethylaminomethyl)-3-hydroxypyridine, 1,10-o-phenanthroline, 3,4,7,8-tetramethyl-1,10-o-diazapine Phenanthrene, 2,9-dimethyl-1,10-o-phenanthroline, 4,7-dimethoxy-1,10-o-phenanthroline, N,N'-bis[(E)-pyridin-2-ylmethylene]cyclohexane-1,2-diamine, N-[(E)-phenylmethylene], N-[(E)-phenylmethylene]-cyclohexylamine, 1,1,1-tris(hydroxymethyl)ethane, n-butylimidazole, ethylene glycol, 2,2,6,6-tetrakis Methylheptane-3,5-dione, 2-(2,2-dimethylpropionyl)cyclohexanone, acetylacetone, dibenzoylmethane, 2-(2-methylpropionyl)cyclohexanone, biphenyl-2-yl(di-tert-butyl)phosphine, vinylbis-(diphenylphosphine), N,N-diethylsalicylamide, 2-hydroxybenzaldehyde oxime, oxy[(2,4,6-trimethylphenyl)amino]acetic acid, or 1H-pyrrole-2-carboxylic acid.

[0592] 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)dichloropalladium(II), bis(allyl)-dichloropalladium(II), or [1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) dichloride.

[0593] Palladium complexes can also be formed in the reaction mixture by separately adding a palladium salt and a ligand or salt 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-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino-2,6'-dimethoxybiphenyl, 2-dicyclohexylphosphino-2',6'-diisopropylbiphenyl, triphenylphosphine, tri-(o-methyl)-bis(thiophene) ... phenyl)phosphine, sodium 3-(diphenylphosphino)benzenesulfonate, tris-(2-methoxy-phenyl)phosphine, 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)ethane, 1,4-bis(dicyclohexylphosphino)butane, 1,2-bis(dicyclohexylphosphino)ethane, 2-(dicyclohexylphosphino)-2'-(N,N-dimethylamino)-biphenyl, 1,1'-bis(diphenylphosphino)-ferrocene, (R)-(-)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, tris-(2,4-tert-butyl-phenyl)phosphite, di(1-adamantyl)-2-morpholinophenylphosphine, or 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride.

[0594] 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).

[0595] Some of the methods described herein can be carried out by metal photoredox catalysis according to methods reported 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 process is then carried out in the presence of a photosensitizer (e.g. Ir and Ru complexes or organic dyes) and a metal catalyst (e.g. Ni complexes). The reaction can be carried out in the presence of a ligand and, if appropriate, in the presence of a base under irradiation with blue or white light.

[0596] 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-isopropylideneacetone-10-acridine perchlorate or tetrafluoroborate, or 2,4,5,6-tetra-9H-carbazol-9-yl-1,3-phthalonitrile, 9-fluorenone and 9,10-phenanthrenequinone.

[0597] Suitable nickel catalysts include, but are not limited to, bis(1,5-cyclooctadiene)nickel(0), nickel(II) chloride, nickel(II) bromide, nickel(II) iodide in anhydrous or hydrated form or as a dimethoxyethane complex; nickel(II) acetylacetonate, nickel(II) nitrate hexahydrate. These nickel catalysts can be used in combination with a bipyridine ligand (e.g., 2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine, 4,4'-dimethyl-2,2'-bipyridine), or o-phenanthroline (e.g., 1,10-o-phenanthroline, 4,7-dimethyl-1,10-o-phenanthroline, 4,7-dimethoxy-1,10-o-phenanthroline), or a diamine (e.g., N,N,N',N'-tetramethylethylenediamine), or a diketone (e.g., tetramethylheptanedione).

[0598] The methods described herein may be carried out at a temperature of -105°C to 250°C, preferably -78°C to 185°C.

[0599] The reaction time varies depending on the reaction scale and reaction temperature, but is usually between several minutes and 48 hours.

[0600] The methods described herein are generally carried out at standard pressure. However, they can also be carried out at elevated or reduced pressure.

[0601] In the methods described herein, the starting materials are generally used in approximately equimolar amounts. However, a relatively large excess of one starting material may also be used.

[0602] Method for preparing the compound of formula (I)

[0603] Method A

[0604] The compound of formula (Ia-1), wherein A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined above, wherein

[0605] A 2 is O,

[0606] T is hydrogen, and

[0607] m is 1 or 2,

[0608] It can be prepared by cyclizing the compound of formula (4)

[0609]

[0610] Among them, m, A 1、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined above, and

[0611] W is hydrogen or an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxy

[0612] phenyl)methyl,

[0613] and

[0614] When W is hydrogen, the compound of formula (4) can be directly obtained by treating it with a dehydrating agent in the presence of a base to obtain the compound of formula (Ia-1).

[0615] or

[0616] When W is an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, the compound of formula (Ia-1) is obtained by treating the compound of formula (4) with a dehydrating agent, optionally in the presence of a base, and then performing a deprotection step, as shown in Scheme 1.

[0617]

[0618] The compound of formula (Ia-1) can be obtained by treating the compound of formula (4) with a dehydrating agent such as POCl3, P2O5 or trifluoromethanesulfonic anhydride, optionally in the presence of a base. This method of forming an oxadiazine ring is known and has been described in the literature (J. Med. Chem. 2017, 60, 2383-2400). The reaction can be carried out in any conventional inert organic solvent. Preference is given to using optionally halogenated aliphatic, cycloaliphatic or aromatic hydrocarbons, for example petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, for example diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, for example acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; alcohols, for example ethanol or isopropanol.

[0619] When W represents an amino protecting group, an additional deprotection step is performed after step 3 using the reaction conditions described in the literature (Greene's Protective Groups inorganic Synthesis; Peter GM Wuts; Wiley; Fifth Edition; 2014; 895-1194). For example, the tert-butyloxycarbonyl group can be removed in an acidic medium such as hydrochloric acid or trifluoroacetic acid.

[0620] Compounds of formula (4) can be prepared by first reacting a compound of formula (1) with an amine of formula (2) or a salt thereof to provide a compound of formula (3), from which the phthalimide group is removed to provide a compound of formula (4);

[0621] Where A in formula (1) 1 , Ring Y, p, R 7 and Q are as defined above and

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

[0623] Where m, R in formula (2) 3 、R 4 、R 5 , L and R 6 As defined above and

[0624] W is hydrogen or an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl,

[0625] Where m, A in formula (3) 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 , Q and W are as defined above.

[0626] The reaction conditions for removing the phthalimide group are well known and reported in the literature (Greene's Protective Groups in organic Synthesis; Peter GM Wuts; Wiley; 5th edition; 2014; 1012-1014).

[0627] Compounds of formula (1) may be prepared by one or more of the methods described herein (see Methods F to M outlined below).

[0628] Amines of formula (2) can be prepared by method O described herein.

[0629] Among them U 1The compound of formula (1) which is a hydroxyl group can be reacted with the amine of formula (2) in the presence of a condensing agent by a method described in the literature (e.g., Tetrahedron 2005, 61, 10827-10852). Examples of suitable condensing agents include, but are not limited to, halogenating agents (e.g., phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride, or thionyl chloride), dehydrating agents (e.g., ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, or methanesulfonyl chloride), carbodiimides (e.g., N,N'-dicyclohexylcarbodiimide (DCC)), or other conventional condensation (or peptide coupling) reagents (e.g., phosphorus pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphinoyl chloride, 1- [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), N,N'-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, tripyrrolidinium phosphonium bromide hexafluorophosphate, or propylphosphonic anhydride (T3P).

[0630] Among them U 1 The compound of formula (1) which is a halogen can be reacted with the amine of formula (2) in the presence of an acid binding agent by well-known methods. Suitable acid binding agents include any inorganic and organic bases commonly used in such reactions as described herein. Preferably, an alkali metal carbonate, an alkaline earth metal acetate, a tertiary amine or an aromatic base.

[0631] Among them U 1 A compound of formula (1) which is a C1-C6-alkoxy group can be reacted with an excess of an amine of formula (2), optionally in the presence of a Lewis acid such as trimethylaluminium.

[0632] Method B

[0633] The compound of formula (Ia-1), wherein A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined above, wherein

[0634] A 2 is O,

[0635] T is hydrogen,

[0636] m is 1 or 2,

[0637] It can also be prepared by reacting a compound of formula (7) with a compound of formula (8) in the presence of a base (e.g., an organic or inorganic base) and optionally in the presence of a suitable copper salt or complex, followed by a deprotection step if W is an amino protecting group, as shown in Scheme 2.

[0638]

[0639] Among them, m, A 1 、R 3 、R 4 、R 5 , L, R 6 , ring Y, p and R 7 As defined above, W is hydrogen or an amino protecting group, preferably hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, more preferably hydrogen,

[0640] and

[0641] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine,

[0642]

[0643] wherein Q is as defined above.

[0644]

[0645]

[0646] The compound of formula (7) can be prepared by reacting a compound of formula (5) with an amine of formula (2) or a salt thereof to obtain a compound of formula (6a) or a salt thereof, removing the phthalimide group of the compound of formula (6a) to obtain a compound of formula (6b), and then, when W is hydrogen, optionally in the presence of a base, directly treating with a dehydrating agent to directly obtain a compound of formula (7).

[0647] or

[0648] When W is an amino protecting group, optionally treated with a dehydrating agent in the presence of a base, and finally deprotected to obtain a compound of formula (7), under the same conditions as described in Method A herein;

[0649] Where A in formula (5) 1 , ring Y, p and R 7 As defined above,

[0650] X is halogen, preferably bromine, and

[0651] U 1 is hydroxy, halogen or C1-C6-alkoxy,

[0652] Where m, R in formula (2) 3 、R 4 、R 5 , L and R 6 as defined above, and

[0653] W is hydrogen or an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl,

[0654] Where m and A in formula (6a) 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 , X and W are as defined above, and

[0655] G is phthalimide,

[0656] Where m and A in formula (6b) 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 , X and W are as defined above, and

[0657] G is NH2.

[0658] The reaction of the compound of formula (7) with the compound of formula (8) 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 as described herein.

[0659] Compounds of formula (5) are commercially available or can be prepared by Method N described herein.

[0660] Compounds of formula (8) are commercially available or can be obtained by transformation or derivatization of another compound of formula (8) according to well-known methods.

[0661] Method C

[0662] The compound of formula (Ia-1) and the compound of formula (Ia-2) can also be prepared by a method comprising the following steps (as shown in Scheme 3):

[0663] Wherein A of formula (Ia-1) 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined above and wherein

[0664] A 2 is O,

[0665] T is hydrogen,

[0666] m is 1 or 2,

[0667] Wherein A of formula (Ia-2) 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined above, and wherein

[0668] A 2 For NH,

[0669] T is hydrogen,

[0670] m is 1 or 2,

[0671] - reacting a compound of formula (10) with a compound of formula (11a) to provide a compound of formula (12),

[0672] -When E 1 and E 2 When the hydroxyl group is present, the Mitsunobu reaction conditions known to those skilled in the art are used (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kürti, Barbara Czako; Elsevier; 2005;

[0673] 294-295 and references therein) converting the compound of formula (12) into the compound of formula (Ia-1),

[0674] -When E 1 is halogen and E 2 When is a hydroxyl group, the compound of formula (12) is converted into the compound of formula (Ia-1) in the presence of a base,

[0675] or

[0676] - reacting a compound of formula (10) with a compound of formula (11b) to provide a compound of formula (13),

[0677] -When E 1 is halogen and E 2 When it is an amino group, the compound of formula (13) is converted into the compound of formula (Ia-2) in the presence of a base.

[0678] The compound of formula (9) (E 1=hydroxy) is commercially available or can be synthesized by the method described in the literature (Molecules, 9(6), 405-426; 2004; WO2017203474). The compound of formula (9) (E 1 =halogen) can be obtained from the corresponding amino alcohol, ie, the compound of formula (9) (E 1 =hydroxy) are obtained by known methods.

[0679]

[0680] Method D

[0681] The compound of formula (Ia-1) can be prepared by a method comprising the following steps (as shown in Scheme 4):

[0682] Among them A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined above and wherein

[0683] A 2 is O,

[0684] T is hydrogen,

[0685] m is 1 or 2,

[0686] - reacting a compound of formula (14) with a compound of formula (11a) to provide a compound of formula (15),

[0687] -When E 1 is hydroxyl and E 2 When the hydroxyl group is present, the Mitsunobu reaction conditions known to those skilled in the art are used (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kürti, Barbara Czako; Elsevier;

[0688] 2005; 294-295 and references therein) converting the compound of formula (15) into the compound of formula (7),

[0689] -When E 1 is halogen and E 2 When is a hydroxyl group, the compound of formula (15) is converted into the compound of formula (7) in the presence of a base,

[0690] Analogously to process B, a compound of formula (7) is reacted with a compound of formula (8) in the presence of a base (eg an organic base or an inorganic base) and optionally in the presence of a suitable copper salt or complex.

[0691]

[0692] When W represents an amino protecting group, step 3 is followed by an additional deprotection step using reaction conditions described in the literature (Greene's Protective Groups inorganic Synthesis; Peter GM Wuts; Wiley; Fifth Edition; 2014; 895-1194) to provide compounds of formula (Ia-1).

[0693] The compound of formula (9) (wherein E 1 = hydroxyl) are commercially available or can be synthesized by methods described in the literature (Molecules, 9 (6), 405-426; 2004; WO2017203474). The compound of formula (9) (wherein E 1 =halogen) can be obtained from the corresponding amino alcohol, ie, a compound of formula (9) (wherein E 1 =halogen) are obtained by known methods.

[0694] Method E

[0695] The compound of formula (Ia-3) can be prepared by reacting a compound of formula (1) with a diamine of formula (16) (as shown in Scheme 5), wherein A of formula (Ia-3) 1 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined above and wherein

[0696] A 2 CR 2A R 2B ,

[0697] T is hydrogen,

[0698] m is 0,

[0699] Where A in formula (1) 1 , Ring Y, p, R 7 and Q are as defined above, and

[0700] U 1 is hydroxy or halogen,

[0701] Where R in formula (16) 2A 、R 2B 、R5 , L and R 6 As defined above.

[0702]

[0703] Method E can be carried out in the presence of a dehydrating agent such as POCl 3 .

[0704] The diamine of formula (16) is commercially available or can be prepared by methods described in the literature ( Eur. J. Med. Chem 1990, 25(1), 35-44; J. Org. Chem 2012, 77(9), 4375-4384; WO2009003867 ).

[0705] Method for preparing the compound of formula (1)

[0706] Compounds of formula (1) can be obtained directly by carrying out one of the methods described below, or can be obtained by transforming or derivatizing another compound of formula (1) prepared according to the methods described herein. Compounds of formulae (1-a) to (1-f) are various subsets of formula (1). Compounds of formulae (1-a1) and (1-a2) are various subsets of formula (1-a), and compounds of formulae (1-b1) and (1-b2) are various subsets of formula (1-b).

[0707] Method F

[0708] The compound of formula (1-a1) can be prepared by reacting a compound of formula (19) with carbon monoxide, carbon dioxide or a reagent of formula (20) (as shown in Scheme 6), wherein Q of formula (1-a1) is as defined above,

[0709] U 1 is hydroxy or C1-C6-alkoxy,

[0710] Y 1 、Y 2 、Y 3 and Y 4 are independently N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 1 、Y 2 、Y 3 and Y 4 No more than three of them are N,

[0711] Wherein Q in formula (19) is as defined above,

[0712] Y 1 、Y 2 、Y 3 and Y4 are independently N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 1 、Y 2 、Y 3 and Y 4 No more than three of them are N, and

[0713] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine,

[0714] In formula (20),

[0715] E 3 is halogen, cyano, C1-C6-alkoxy or C1-C 6- an alkoxycarbonyloxy group, and

[0716] U 2 It is a C1-C6-alkoxy group.

[0717]

[0718]

[0719] The compound of formula (17) is commercially available or can be prepared according to the methods described in the literature (WO2012162254, WO2010116084).

[0720] Compounds of formula (8) are commercially available or can be obtained by conversion or derivatization of another compound of formula (8) according to known methods.

[0721] The compound of formula (19) can be prepared from the compound of formula (17) (wherein Y 1 、Y 2 、Y 3 and Y 4 are independently N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 1 、Y 2 、Y 3 and Y 4 No more than three of them are N, and

[0722] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine) is prepared by reacting a compound of formula (17) with a reagent of formula (8) (wherein Q is as defined above) in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (18) (wherein Q is as defined above, and Y 1 、Y 2 、Y 3 and Y4 are independently N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 1 、Y 2 、Y 3 and Y 4 wherein no more than three are N), the compound of formula (18) is converted to the compound of formula (19) in the presence of a halogenating agent (such as POCl3, POBr3, PCl3 or PBr3) (see WO2012162254).

[0723] Compounds of formula (1-a1) can be prepared by treating compounds of formula (19) with:

[0724] -nBuLi and carbon dioxide or a reagent of formula (20) or

[0725] - carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0726] Method G

[0727] Compounds of formula (1-a2) can be prepared by reacting a compound of formula (23) (wherein Q is as defined above) with carbon monoxide, carbon dioxide or a reagent of formula (20) (as shown in Scheme 7),

[0728] wherein Q in formula (1-a2) is as defined above

[0729] U 1 is hydroxy or C1-C6-alkoxy,

[0730] Y 5 、Y 6 and Y 7 are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y 7 No more than two of them are heteroatoms,

[0731] Wherein Q in formula (23) is as defined above

[0732] Y 5 、Y 6 and Y 7 are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y7 No more than two of them are heteroatoms, and

[0733] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine,

[0734] In formula (20),

[0735] E 3 is halogen, cyano, C1-C6-alkoxy or C1-C 6- an alkoxycarbonyloxy group, and

[0736] U 2 It is a C1-C6-alkoxy group.

[0737]

[0738] The compound of formula (21) is commercially available or can be prepared according to the methods described in the literature (WO2017133667; J. Org. Chem. 2004, 79, 10311-10322; Monatshefte für Chemie 1986, 117, 221-230).

[0739] Compounds of formula (23) can be prepared from compounds of formula (21) by reacting with a reagent of formula (8) (wherein Q is as defined above) in the presence of a base and optionally in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (22), treating the compound of formula (22) with a halogenating agent such as bromine, iodine, NCS (N-chlorosuccinimide) or NBS (N-bromosuccinimide) in the presence of a base as described herein to form a compound of formula (23),

[0740] In formula (21)

[0741] Y 5 、Y 6 and Y 7 are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y 7 No more than two of them are heteroatoms, and

[0742] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine,

[0743] wherein Q in formula (22) is as defined above, and

[0744] Y 5 、Y 6 and Y 7are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y 7 No more than two of them are heteroatoms,

[0745] Wherein Q in formula (23) is as defined above,

[0746] Y 5 、Y 6 and Y 7 are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y 7 No more than two of them are heteroatoms, and

[0747] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine.

[0748] Compounds of formula (1-a2) can be prepared by treating compounds of formula (23) with:

[0749] - a base (e.g. nBuLi) and carbon dioxide or a reagent of formula (20) or

[0750] - carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0751] Method H

[0752] The compound of formula (1-b1) can be prepared by reacting a compound of formula (26) with carbon monoxide, carbon dioxide or a reagent of formula (20) (as shown in Scheme 8).

[0753] Where Q and R in formula (1-b1) 8 As defined above,

[0754] U 1 is hydroxy or C1-C6-alkoxy,

[0755] Y 1 、Y 2 、Y 3 and Y 4 are independently N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 1 、Y 2 、Y 3 and Y 4No more than three of them are N,

[0756] Where Q and R in formula (26) 8 As defined above,

[0757] Y 1 、Y 2 、Y 3 and Y 4 are independently N, CH or CR 7 , where R 7 As defined above, the conditions are variables Y1, Y 2 、Y 3 and Y 4 No more than three of them are N, and

[0758] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine,

[0759] In formula (20),

[0760] E 3 is halogen, cyano, C1-C6-alkoxy or C1-C 6- an alkoxycarbonyloxy group, and

[0761] U 2 It is a C1-C6-alkoxy group.

[0762]

[0763]

[0764] The compound of formula (24) is commercially available or can be prepared according to the methods described in the literature (WO2012162254, WO2010116084).

[0765] Compounds of formula (8) are commercially available or can be obtained by conversion or derivatization of another compound of formula (8) according to known methods.

[0766] Compounds of formula (26) can be prepared from compounds of formula (24) by reacting the compound of formula (24) with a reagent of formula (8) (wherein Q is as defined above) in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (25), and converting the compound of formula (25) to a compound of formula (26):

[0767] -When W 1 When it is hydrogen, directly in the presence of dehydrating agents such as POCl3, POBr3, PCl3 or PBr3,

[0768] -When W 1When W is benzyl, a deprotection step is performed to obtain a compound of formula (25), wherein W 1 to hydrogen, and then the resulting compound is converted into a compound of formula (26) in the presence of a dehydrating agent such as POCl 3 , POBr 3 , PCl 3 or PBr 3 .

[0769] Where R in formula (24) 8 As defined above,

[0770] Y 1 、Y 2 、Y 3 and Y 4 are independently N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 1 、Y 2 、Y 3 and Y 4 No more than three of them are N,

[0771] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine, and

[0772] W 1 is hydrogen or benzyl,

[0773] Where Q and R in formula (25) 8 As defined above,

[0774] Y 1 、Y 2 、Y 3 and Y 4 are independently N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 1 、Y 2 、Y 3 and Y 4 No more than three of them are N, and

[0775] W 1 is hydrogen or benzyl.

[0776] Compounds of formula (1-b1) can be prepared by treating compounds of formula (26) with:

[0777] -nBuLi and carbon dioxide or a reagent of formula (20) or

[0778] - carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0779] Method I

[0780] The compound of formula (1-b2) can be prepared by reacting a compound of formula (29) with carbon monoxide, carbon dioxide or a reagent of formula (20) (as shown in Scheme 9), wherein Q and R of formula (1-b2) are 8 As defined above,

[0781] U 1 is hydroxy or C1-C6-alkoxy,

[0782] Y 5 、Y 6 and Y 7 are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y 7 No more than two of them are heteroatoms,

[0783] Where Q and R in formula (29) 8 As defined above,

[0784] Y 5 、Y 6 and Y 7 are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y 7 No more than two of them are heteroatoms, and

[0785] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine,

[0786] In formula (20),

[0787] E 3 is halogen, cyano, C1-C6-alkoxy or C1-C 6- an alkoxycarbonyloxy group, and

[0788] U 2 It is a C1-C6-alkoxy group.

[0789]

[0790]

[0791] The compound of formula (27) is commercially available or can be prepared by the methods described in the literature (WO2005095401; WO2018067422; WO2016106106; WO2014144455; WO2013086397).

[0792] Compounds of formula (29) can be prepared by reacting a compound of formula (27) with a reagent of formula (8) (wherein Q is as defined above) in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (28), and converting the compound of formula (28) to a compound of formula (29)

[0793] -When W 1 When it is hydrogen, directly in the presence of a dehydrating agent such as POCl3, POBr3, PCl3 or PBr3,

[0794] -When W 1 When W is benzyl, a deprotection step is performed to obtain a compound of formula (28), wherein W 1 is hydrogen, and then the resulting compound is converted into a compound of formula (26) in the presence of a dehydrating agent such as POCl3, POBr3, PCl3 or PBr3,

[0795] Where R in formula (27) 8 As defined above,

[0796] Y 5 、Y 6 and Y 7 are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y 7 No more than two of them are heteroatoms,

[0797] X is halogen, preferably fluorine, chlorine or bromine, more preferably bromine, and

[0798] W 1 is hydrogen or benzyl,

[0799] Where Q and R in formula (28) 8 As defined above,

[0800] Y 5 、Y 6 and Y 7 are independently O, S, N, CH or CR 7 , where R 7 As defined above, the condition is the variable Y 5 、Y 6 and Y 7 No more than two of them are heteroatoms, and

[0801] W 1 is hydrogen or benzyl.

[0802] Compounds of formula (1-b2) can be prepared by treating compounds of formula (29) with:

[0803] -nBuLi and carbon dioxide or a reagent of formula (20) or

[0804] - carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0805] Method J

[0806] The compound of formula (1-c) can be prepared by reacting a compound of formula (33) with carbon dioxide or a reagent of formula (20) (as shown in Scheme 10), wherein Q, p and R of formula (1-c) are 7 As defined above,

[0807] U 1 is hydroxy or C1-C6-alkoxy,

[0808] Y 8 is O, S or NY', wherein Y' is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl, and

[0809] x 3 is 1, 2, or 3,

[0810] Where Q, p and R in formula (33) 7 As defined above,

[0811] Y 8 is O, S or NY', wherein Y' is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl, and

[0812] x 3 is 1, 2, or 3,

[0813] In formula (20),

[0814] E 3 is halogen, cyano, C1-C6-alkoxy or C1-C 6- an alkoxycarbonyloxy group, and

[0815] U 2 It is a C1-C6-alkoxy group.

[0816]

[0817]

[0818] Compounds of formula (30) and (31) are commercially available.

[0819] Compounds of formula (8) are commercially available or can be obtained by conversion or derivatization of another compound of formula (8) according to known methods.

[0820] Compounds of formula (33) can be prepared from compounds of formula (30) by reacting the compound with a reagent of formula (31) in the presence of a base and optionally in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (32), and reacting the compound of formula (32) with a reagent of formula (8) in the presence of a base and a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (33).

[0821] Compounds of formula (1-c) can be prepared by treating compounds of formula (33) with a base (eg, nBuLi) and carbon dioxide or a reagent of formula (20).

[0822] Method K

[0823] The compound of formula (1-d) can be prepared by reacting a compound of formula (36) with carbon dioxide or a reagent of formula (20) (as shown in Scheme 11), wherein Q, p, R 7 and R 8 As defined above,

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

[0825] Y 8 is O, S or NY', wherein Y' is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl, and

[0826] x 3 is 1, 2, or 3,

[0827] Where Q, p, and R in formula (36) 7 and R 8 As defined above,

[0828] Y 8 is O, S or NY', wherein Y' is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl, and

[0829] x 3 is 1, 2, or 3,

[0830] In formula (20),

[0831] E 3 is halogen, cyano, C1-C6-alkoxy or C1-C 6- an alkoxycarbonyloxy group, and

[0832] U2 It is a C1-C6-alkoxy group.

[0833]

[0834]

[0835] Compounds (31) and (34) are commercially available.

[0836] Compounds of formula (8) are commercially available or can be obtained by conversion or derivatization of another compound of formula (8) according to known methods.

[0837] Compounds of formula (36) can be prepared from compounds of formula (34) by reacting the compound with a reagent of formula (31) in the presence of a base and, optionally, a suitable transition metal catalyst salt or complex as described herein, to form a compound of formula (35), and reacting the compound of formula (35) with a reagent of formula (8) in the presence of a suitable transition metal catalyst salt or complex as described herein to form a compound of formula (36).

[0838] Compounds of formula (1-d) can be prepared by treating compounds of formula (36) with a base (eg, nBuLi) and carbon dioxide or a reagent of formula (20).

[0839] Method L

[0840] Compounds of formula (1-e) can be prepared by reacting a compound of formula (38) with a reagent of formula (39) in the presence of a metal-photoredox catalyst as described herein and a base (e.g., an organic or inorganic base) (as shown in Scheme 12), wherein Q, p, and R of formula (1-e) are 7 As defined above,

[0841] U 1 is hydroxy or C1-C6-alkoxy,

[0842] Y 1 O, S, S(=O)2, CH or CR 7 , where R 7 As defined above,

[0843] x 1 is 1 or 2, and

[0844] x 2 is 1, 2, or 3,

[0845] Wherein Q in formula (38) is as defined above,

[0846] U 1 is hydroxy or C1-C6-alkoxy, and

[0847] X is a halogen,

[0848] Where p and R in formula (39) 7 As defined above,

[0849] x 1 is 1 or 2, and

[0850] x 2 1, 2, or 3.

[0851]

[0852] Compounds of formula (38) can be prepared by reacting a compound of formula (37) with a reagent of formula (8) in the presence of a base and optionally a suitable transition metal catalyst salt or complex as described herein.

[0853] Compounds of formula (37) are commercially available.

[0854] Compounds of formula (8) are commercially available or can be obtained by conversion or derivatization of another compound of formula (8) according to known methods.

[0855] Method M

[0856] Compounds of formula (1-f) can be prepared by reacting a compound of formula (5-a) with a reagent of formula (8) in the presence of a base (e.g., an organic or inorganic base) and optionally a suitable transition metal catalyst salt or complex as described herein (as shown in Scheme 13), wherein Q, ring Y, p and R of formula (1-f) are 7 As defined above, and

[0857] U 1 is a C1-C6-alkoxy group,

[0858] wherein the ring Y, p and R of formula (5-a) 7 As defined above,

[0859] U 1 is a C1-C6-alkoxy group, and

[0860] X is a halogen,

[0861] wherein Q in formula (8) is as defined above.

[0862]

[0863] The compound of formula (5-a) can be prepared from the compound of formula (43) in the presence of a halogenating agent such as POCl3, POBr3, PCl3 or PBr3.

[0864] The compound of formula (43) can be prepared from compounds of formula (40) and formula (41) by the method described in the document (WO2018125800).

[0865] Compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f) (wherein U 1 is C1-C6-alkoxy) can be converted into compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f) (where U is C1-C6-alkoxy) by well-known functional group conversion methods 1 is a hydroxyl group), for example by hydrolysis of the ester group using LiOH in tetrahydrofuran / water.

[0866] Compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f) (wherein U 1 is a hydroxyl group), can be converted into compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e) and (1-f) (wherein U 1 is a halogen). Suitable halogenating agents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride, and thionyl chloride.

[0867] Method for preparing the compound of formula (5)

[0868] The compounds of formula (5-a) are various subsets of formula (5).

[0869] Method N

[0870] The compound of formula (5) can be prepared by reacting a compound of formula (44) with a base and carbon dioxide or a reagent of formula (20) (as shown in Scheme 14), wherein A of formula (5) 1 , ring Y, p and R 7 As defined above,

[0871] U 1 is hydroxy or C1-C6-alkoxy, and

[0872] X is a halogen,

[0873] Where A in formula (44) 1 , ring Y, p and R 7 As defined above, and

[0874] X is a halogen,

[0875] In formula (20),

[0876] E 3is halogen, cyano, C1-C6-alkoxy or C1-C 6- an alkoxycarbonyloxy group, and

[0877] U 2 It is a C1-C6-alkoxy group.

[0878]

[0879] The compound of formula (44) is commercially available or can be found in the literature (WO2017004500; WO2017112719; WO2016115272; WO2011015343; WO2017023905; WO2017112678; Monatshefte für Chemie 2018, 149, 1857-1864; WO2005095401; WO2018067422; WO2016106106; WO2014144455; WO2013086397; WO20140121198; WO2011145287; WO2012098387; Eur. J. Med. Chem. 2017, 138, 816-829).

[0880] Compounds of formula (20) are commercially available.

[0881] Preparation methods of compounds of formula (2) and formula (9)

[0882] Compounds of formula (9-a) and (9-b) are various subsets of formula (9).

[0883] Method O

[0884] The compound of formula (9-a) can be converted into the corresponding compound of formula (2) or (9-b) (as shown in Scheme 15) by methods described in the literature, wherein L, R 3 、R 4 、R 5 and R 6 As defined above,

[0885] m is 1 or 2, and

[0886] W is hydrogen or an amino protecting group, preferably hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.

[0887]

[0888] The amino functionality of the compound of formula (9-a) wherein W is hydrogen can be first protected according to known methods to provide a compound of formula (9-a), wherein W is an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl (Greene's Protective Groups in organic Synthesis; Peter GM Wuts; Wiley; Fifth Edition; 2014; 895-1194).

[0889] Compounds of formula (9-a) can then be converted to compounds of formula (2) using classical Mitsunobu reaction conditions known to those skilled in the art (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kürti, Barbara Czako; Elsevier; 2005; 294-295 and references therein).

[0890] Among them E 1 The compound of formula (9-a) which is a hydroxyl group can be converted into a compound of formula (9-b) by a well-known method in the presence of a halogenating agent, wherein E 1 Suitable halogenating agents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride, and thionyl chloride.

[0891] Amino alcohols of formula (9-a, W = hydrogen) are commercially available or can be prepared by methods described in the literature (Molecules, 9 (6), 405-426; 2004, WO2017203474).

[0892] intermediates

[0893] The present invention also relates to intermediates useful in the preparation of compounds of formula (I).

[0894] The compounds of formula (1) are valuable intermediates for preparing compounds of formula (I),

[0895]

[0896] Among them A 1 , Q, ring Y, p and R 7 As defined in formula (I), and

[0897] U 1 is hydroxy, halogen or C1-C6-alkoxy.

[0898] Regarding A given in formula (I) 1, Q, ring Y, p and R 7 The preferred, more preferred, even more preferred and most preferred definitions apply mutatis mutandis.

[0899] U 1 Preferred are hydroxy, fluorine, chlorine, bromine, methoxy, ethoxy or tert-butoxy.

[0900] Compounds of formula (2) are also valuable intermediates for the preparation of compounds of formula (I),

[0901]

[0902] Among them, L, R 5 and R 6 As defined in formula (I),

[0903] m is 1 or 2, preferably 1,

[0904] R 3 and R 4 are independently hydrogen, halogen or C1-C6-alkyl,

[0905] or

[0906] R 3 and R 4 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl-ring,

[0907] and

[0908] W is hydrogen or an amino protecting group, preferably hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.

[0909] Regarding L and R given in formula (I) 5 and R 6 The preferred, more preferred, even more preferred and most preferred definitions apply mutatis mutandis.

[0910] R 3 and R 4 Preferably, R is independently selected from hydrogen, fluorine, chlorine and C1-C4-alkyl, more preferably selected from hydrogen, fluorine and C1-C4-alkyl, even more preferably selected from hydrogen, fluorine, methyl, ethyl, n-propyl and isopropyl. Most preferably, R 3 and R 4 All are hydrogen.

[0911] The present invention also relates to compounds of formula (3) and (4):

[0912]

[0913] in

[0914] A 1 、R3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined in formula (I),

[0915] m is 1 or 2, preferably 1,

[0916] and

[0917] W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.

[0918] Regarding A given in formula (I) 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 The preferred, more preferred, even more preferred and most preferred definitions of and Q apply mutatis mutandis.

[0919] The present invention also relates to compounds of formula (7)

[0920]

[0921] in

[0922] A 1 、R 3 、R 4 、R 5 , L, R 6 , ring Y, p and R 7 As defined in formula (I),

[0923] m is 1 or 2, preferably 1,

[0924] and

[0925] X is halogen, preferably fluorine, chlorine or bromine.

[0926] Regarding A given in formula (I) 1 、R 3 、R 4 、R 5 , L, R 6 , ring Y, p and R 7 The preferred, more preferred, even more preferred and most preferred definitions apply mutatis mutandis.

[0927] The present invention also relates to compounds of formula (10) and (12):

[0928]

[0929] in

[0930] A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined in formula (I),

[0931] m is 1 or 2, preferably 1,

[0932] E 1 is hydroxy or halogen, preferably hydroxy, chlorine or bromine,

[0933] E 2 is a hydroxyl group or an amino group,

[0934] and

[0935] W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.

[0936] Regarding A given in formula (I) 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 The preferred, more preferred, even more preferred and most preferred definitions of and Q apply mutatis mutandis.

[0937] The present invention also relates to compounds of formula (14) and (15):

[0938]

[0939] in

[0940] A 1 、R 3 、R 4 、R 5 , L, R 6 , ring Y, p and R 7 As defined in formula (I),

[0941] m is 1 or 2,

[0942] X is halogen, preferably fluorine, chlorine or bromine,

[0943] E 1 is hydroxy or halogen, preferably hydroxy, chlorine or bromine,

[0944] E 2 is hydroxyl,

[0945] and

[0946] W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.

[0947] Regarding A given in formula (I) 1 、R 3 、R 4 、R 5 , L, R 6 , ring Y, p and R 7 The preferred, more preferred, even more preferred and most preferred definitions apply mutatis mutandis.

[0948] Compositions and formulations

[0949] The present invention further relates to compositions, in particular compositions for controlling unwanted microorganisms. Said compositions can be applied to the microorganisms and / or their habitat.

[0950] described Composition It comprises at least one compound of formula (I) and at least one agriculturally suitable adjuvant, such as a carrier and / or a surfactant.

[0951] carrierA solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert. The carrier generally allows for 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, particularly ammonium sulfate, ammonium phosphate, and ammonium nitrate; natural rock powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth; silica gel and synthetic rock powders such as finely divided silica, alumina, and silicates. Examples of typical useful solid carriers for preparing granules include, but are not limited to, crushed and classified natural rocks such as calcite, marble, pumice, sepiolite, and dolomite, synthetic particles of inorganic and organic powders, and particles of organic materials such as paper, sawdust, coconut shells, corn cobs, and tobacco straw. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and nonpolar organic chemical liquids, such as aromatic and nonaromatic hydrocarbons (e.g. cyclohexane, alkanes, alkylbenzenes, xylene, toluene, tetralin, alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride or dichloromethane), alcohols or polyols (which may optionally be substituted, etherified and / or esterified, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or ethylene glycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, their amides (e.g. dimethylformamide or fatty acid amides) and esters, lactams (e.g. N-alkylpyrrolidones, in particular N-methylpyrrolidone) and lactones, sulfones and sulfoxides (e.g. dimethyl sulfoxide), vegetable oils or oils of animal origin. The carrier may also be a liquefied gas extender, ie a liquid which is gaseous at standard temperature and standard pressure, for example aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide.

[0952] Preferred solid carriers are selected from clay, talc and silica.

[0953] Preferred liquid carriers are selected from water, fatty acid amides and esters thereof, aromatic and non-aromatic hydrocarbons, lactams and carbonates.

[0954] The amount of carrier is generally from 1 to 99.99%, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, most preferably from 20 to 99%, based on the weight of the composition.

[0955] The liquid carrier is generally present at 20 to 99%, such as 30 to 80%, by weight of the composition.

[0956] The solid carrier is generally present at 0 to 50%, preferably 5 to 45%, such as 10 to 30%, based on the weight of the composition.

[0957] If the composition comprises two or more carriers, the above ranges refer to the total amount of the carriers.

[0958] described surfactants The surfactant may be an ionic (cationic or anionic), amphoteric or nonionic surfactant, such as an ionic or nonionic emulsifier, foaming agent, dispersant, wetting agent, penetration enhancer, or any mixture of these surfactants. Examples of suitable surfactants include, but are not limited to, polyacrylates, lignin sulfonates (e.g., sodium lignin sulfonate), phenol sulfonates or naphthalene sulfonates, polycondensates of ethylene oxide and / or propylene oxide with fatty alcohols, fatty acids or fatty amines (e.g., polyoxyethylene fatty acid esters, such as castor oil ethoxylates; polyoxyethylene fatty alcohol ethers, such as alkylaryl polyethylene glycol ethers), substituted phenols (preferably alkylphenols or arylphenols) and their ethoxylates (e.g., tristyrylphenol ethoxylates), salts of sulfosuccinates, taurine derivatives (preferably alkyl taurates), phosphates of polyethoxylated alcohols or phenols, fatty esters of polyols (e.g., fatty acid esters of glycerol, sorbitol or sucrose), sulfates (e.g., alkyl sulfates and alkyl ether sulfates), sulfonates (e.g., alkyl sulfonates, aryl sulfonates and alkylbenzene sulfonates), phosphates, protein hydrolyzates, lignin sulfate waste liquors and methylcellulose. Any salt mentioned in this paragraph preferably refers to the respective alkali metal salts, alkaline earth metal salts and ammonium salts.

[0959] Preferred surfactants are selected from polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, alkylbenzene sulfonates such as calcium dodecylbenzene sulfonate, castor oil ethoxylate, sodium lignin sulfonate and arylphenol ethoxylates such as tristyrylphenol ethoxylate.

[0960] The amount of surfactant is typically from 5 to 40%, for example from 10 to 20%, based on the weight of the composition.

[0961] Suitable additivesOther examples of the present invention include water repellents, desiccants, binders (adhesives, tackifiers, fixatives such as carboxymethylcellulose, natural and synthetic polymers in powder, granule or latex form (e.g. gum arabic, polyvinyl alcohol and polyvinyl acetate), natural phospholipids (e.g. cephalin and lecithin) and synthetic phospholipids, polyvinylpyrrolidone and teloacetate), thickeners and secondary thickeners (e.g. cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays such as those available under the name Bentone, and finely divided silica), stabilizers (e.g. cold stabilizers), preservatives (e.g. dichlorobenzene and benzyl alcohol semi-solids), Formal), antioxidants, light stabilizers (especially UV stabilizers) or other agents that improve chemical and / or physical stability), dyes or pigments (for example inorganic pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes), defoamers (for example silicone defoamers and magnesium stearate), antifreeze agents, adhesives, gibberellins and processing aids, mineral and vegetable oils, fragrances, waxes, nutrients (including trace nutrients such as iron salts, manganese salts, boron salts, copper salts, cobalt salts, molybdenum salts and zinc salts), protective colloids, thixotropic substances, penetrants, chelating agents and complex formers.

[0962] The choice of adjuvant is related to the intended mode of administration of the compound of formula (I) and / or the physical properties of the compound. In addition, adjuvants can be selected to impart specific properties (technical, physical and / or biological properties) to the composition or the use forms prepared therefrom. The choice of adjuvant can allow the composition to be customized according to specific needs.

[0963] The compositions of the present invention can be provided to the end user in the form of a ready-to-use formulation, i.e., a composition that can be applied directly to plants or seeds by suitable equipment such as spraying or dusting devices. Alternatively, the compositions can be provided to the end user in the form of a concentrate that must be diluted, preferably with water, before use.

[0964] The compositions of the invention can be prepared in conventional manner, for example by mixing a compound of formula (I) with one or more suitable auxiliaries (for example as disclosed above).

[0965] The composition comprises a compound of formula (I) of a fungicidal effective amount. The term "effective amount" is an amount sufficient to prevent and treat harmful fungi on cultivated plants or in protected materials, and can not cause substantial damage to the treated plants. Such an amount can vary within a wide range and depends on various factors, such as the fungus species to be prevented and treated, the cultivated plants or materials to be treated, climatic conditions and the specific compound of formula (I) used. Typically, the composition according to the present invention comprises 0.01 to 99 weight %, preferably 0.05 to 98 weight %, more preferably 0.1 to 95 weight %, even more preferably 0.5 to 90 weight %, most preferably 1 to 80 weight % of the compound of formula (I). The composition may comprise two or more compounds of the present invention. In this case, the above-mentioned range refers to the total amount of compound of the present invention.

[0966] The composition of the present invention can be any conventional Composition form , such as solutions (e.g. aqueous solutions), emulsions, water-based and oil-based suspensions, powders (e.g. wettable powders, soluble powders), dusts, pastes, granules (e.g. soluble granules, granules for broadcasting), suspo-emulsion concentrates, natural or synthetic products impregnated with compounds of formula (I), fertilizers, and microcapsules in polymeric substances. The compounds of formula (I) may be in suspended, emulsified or dissolved form. The example of particularly suitable composition form is solution, water-soluble concentrate (such as SL, LS), dispersible concentrate (DC), suspending agent and suspension concentrate (such as SC, OD, OF, FS), emulsifiable concentrate (such as EC), emulsion (such as EW, EO, ES, ME, SE), capsule (such as CS, ZC), paste, lozenge, wettable powder or dust (such as WP, SP, WS, DP, DS), compressed tablet (such as BR, TB, DT), granule (such as WG, SG, GR, FG, GG, MG), insecticide (such as LN) and for processing plant propagation material such as seed gel preparation (such as GW, GF). These and other composition types are defined by the Food and Agriculture Organization of the United Nations (FAO). The summary given is referring to " Catalogue of pesticide formulation types and international coding system ", Technical Monograph No.2, the 6th edition May 2008, Croplife International.

[0967] Preferably, the composition of the present invention is in the form of one of the following types: EC, SC, FS, SE, OD and WG, more preferably EC, SC, OD and WG.

[0968] Further details on examples of composition types and their preparation are given below. If two or more compounds of the invention are present, the amount of the compound of the invention as summarized refers to the total amount of the compound of the invention. This also applies to any other components of the composition, if two or more such components are present (e.g., wetting agents, binders).

[0969] i) Water-soluble concentrates (SL, LS)

[0970] 10-60% by weight of at least one compound of formula (I) and 5-15% by weight of a surfactant (e.g., a polyoxyethylene fatty alcohol ether) are dissolved in a corresponding amount of water and / or a water-soluble solvent (e.g., an alcohol such as propylene glycol, or a carbonate such as propylene carbonate) to give a total amount of 100% by weight. Prior to application, the concentrate is diluted with water.

[0971] ii) Dispersible Concentrates (DC)

[0972] 5-25 wt% of at least one compound of formula (I) and 1-10 wt% of a surfactant and / or binder (e.g. polyvinylpyrrolidone) are dissolved in a corresponding amount of an organic solvent (e.g. cyclohexanone) to give a total amount of 100 wt%. The mixture is diluted with water to obtain a dispersant.

[0973] iii) Emulsifiable Concentrates (EC)

[0974] 15-70% by weight of at least one compound of formula (I) and 5-10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a corresponding amount of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon or a fatty acid amide), and if necessary, a water-soluble solvent is added to give a total amount of 100% by weight. The mixture is diluted with water to obtain an emulsion.

[0975] iv) Emulsions (EW, EO, ES)

[0976] 5-40% by weight of at least one compound of formula (I) and 1-10% by weight of a surfactant (e.g., a mixture of calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40% by weight of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). The mixture is added to a corresponding amount of water using an emulsifier to obtain a total amount of 100% by weight. The resulting composition is a homogeneous emulsion. The emulsion can be further diluted with water before application.

[0977] v) Suspension concentrates and suspension concentrates

[0978] v-1) Water-based (SC, FS)

[0979] In a suitable grinding apparatus (e.g., a stirred ball mill), 20-60% by weight of at least one compound of formula (I) is pulverized with 2-10% by weight of a surfactant (e.g., sodium lignin sulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight of a thickener (e.g., xanthan gum), and water to obtain a fine suspension of the active substance. Water is added in an amount to give a total amount of 100% by weight. Dilution with water gives a stable suspension of the active substance. For FS-type compositions, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0980] v-2) Oil-based (OD, OF)

[0981] In a suitable grinding apparatus (e.g., a stirred ball mill), 20-60% by weight of at least one compound of formula (I) is comminuted with 2-10% by weight of a surfactant (e.g., sodium ligninsulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight of a thickener (e.g., a modified clay, in particular bentone or silica), and an organic carrier to obtain a fine oil suspension of the active substance. The organic carrier is added in an amount corresponding to a total amount of 100% by weight. Dilution with water gives a stable dispersion of the active substance.

[0982] vi) Water-dispersible granules and water-soluble granules (WG, SG)

[0983] 50-80% by weight of at least one compound of formula (I) is finely ground with added surfactants (e.g. sodium lignin sulfonate and polyoxyethylene fatty alcohol ether) and converted into water-dispersible or water-soluble granules using technical equipment (e.g. extrusion, spray tower, fluidized bed). The surfactant is used in an amount corresponding to a total amount of 100% by weight. Dilution with water gives a stable dispersion or solution of the active substance.

[0984] vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

[0985] In a rotor-stator mill, 50-80% by weight of at least one compound of formula (I) is finely ground with 1-8% by weight of a surfactant (e.g., sodium ligninsulfonate, polyoxyethylene fatty alcohol ether) and a corresponding amount of a solid carrier (e.g., silica gel) to a total amount of 100% by weight. Dilution with water gives a stable dispersion or solution of the active substance.

[0986] viii) Gel (GW, GF)

[0987] In a stirred ball mill, 5-25% by weight of at least one compound of formula (I) is comminuted with 3-10% by weight of a surfactant (e.g., sodium ligninsulfonate), 1-5% by weight of a binder (e.g., carboxymethylcellulose), and the corresponding amount of water to give a total amount of 100% by weight. This results in a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

[0988] ix) Microemulsion (ME)

[0989] 5-20% by weight of at least one compound of formula (I) is added to 5-30% by weight of an organic solvent mixture (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant mixture (e.g., polyoxyethylene fatty alcohol ether and arylphenol ethoxylate) and a corresponding amount of water to give a total amount of 100% by weight. The mixture is stirred for 1 hour to spontaneously produce a thermodynamically stable microemulsion.

[0990] x) Microcapsules (CS)

[0991] An oil phase containing 5-50% by weight of at least one compound of formula (I), 0-40% by weight of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon), and 2-15% by weight of acrylic monomers (e.g., methyl methacrylate, methacrylic acid, and di- or triacrylates) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Free radical polymerization initiated by a free radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5-50% by weight of at least one compound of formula (I), 0-40% by weight of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethylene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. The monomer amount is 1-10% by weight, based on the weight of the total CS composition.

[0992] xi) Powders (DP, DS)

[0993] 1 to 10% by weight of at least one compound of the formula (I) are ground finely and intimately mixed with a corresponding amount of solid carrier (eg finely divided kaolin) to give a total amount of 100% by weight.

[0994] xii) Granules (GR, FG)

[0995] 0.5-30% by weight of at least one compound of formula (I) are finely ground and combined with a corresponding amount of a solid carrier (eg a silicate) to give a total amount of 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed.

[0996] xiii) Ultra-low volume liquid (UL)

[0997] 1 to 50% by weight of at least one compound of the formula (I) is dissolved in a corresponding amount of an organic solvent (eg an aromatic hydrocarbon) to give a total amount of 100% by weight.

[0998] Composition types i) to xiii) may optionally comprise further auxiliaries, for example 0.1-1% by weight of preservatives, 0.1-1% by weight of antifoams, 0.1-1% by weight of dyes and / or pigments and 5-10% by weight of antifreeze agents.

[0999] mixture / composition

[1000] 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, biological control agents or herbicides. Mixtures with fertilizers, growth regulators, safeners, nitrification inhibitors, semi-chemicals and / or other agriculturally useful preparations are also possible. This can broaden the spectrum of activity or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in Pesticide Manual, 17th edition.

[1001] Examples of fungicides that can be mixed with the compounds of formula (I) and the compositions of the invention are:

[1002] 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 sulfate), (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) trichlorfonazole 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, (1.031) (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-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate Thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.0 48) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-( 2-[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) mefentrifluconazoline le), (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-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)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylthio)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylthio)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole N-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]thio}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]thio}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)thio]phenoxy}phenyl) -N-ethyl-N-methyliminocarboxamide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)thio]phenoxy}phenyl)-N-ethyl-N-methyliminocarboxamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide, (1.072) N'-(4-{[3-(difluoromethoxy)phenyl]thio}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, (1.073) N'-(4-{3-[(difluoromethyl)thio]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarboxamide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methyliminocarboxamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methyliminocarboxamide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl -N-methyliminocarboxamide, (1.078) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide and (1.081) ipfentrifluconazole, (1.082) 2-[4-(4-chlorophenoxy)-2 -(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.085) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]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-methyliminocarboxamide, (1.088) N'-{5-bromo-2-methyl-6-[(1-propoxyprop-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (1.089) hexaconazole, (1.090) penconazole, (1.091) fenbuconazole, (1.092) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionic acid methyl ester, (1.093) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionic acid.

[1003] 2) Inhibitors of respiratory chain complex I or II, for example (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) pyrazoline naphthamide isopyrazam (trans epimeric enantiomers 1R, 4S, 9S), (2.011) pyrazolamine (trans epimeric enantiomers 1S, 4R, 9R), (2.012) pyrazolamine (trans epimeric racemates 1RS, 4SR, 9SR), (2.013) pyrazolamine (mixture of cis epimeric racemates 1RS, 4SR, 9RS and trans epimeric racemates 1RS, 4SR, 9SR), (2.014) pyrazolamine (cis epimeric enantiomers 1R, 4S, 9R), (2.015) pyrazolamine (cis epimeric enantiomers 1S, 4R, 9S), (2.016) pyrazolamine (cis (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 ]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) inpyrfluxam, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, ( 2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2 -ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) 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-methoxyprop-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-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-carboxamide, (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 amine, (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) (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.

[1004] 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) famoclostrobin, xadone), (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) pyrame tostrobin), (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[ (2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029)029) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) metyltetraprole, (3.031) florylpicoxamid.

[1005] 4) Inhibitors of mitosis and cell division, for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridachlometyl, (4.010) thiabendazole, (4.011) thiophanate-methyl, (4.012) thiophanate-methyl, (4.013) thiophanate-methyl, (4.014) thiophanate-methyl, (4.015) thiophanate-methyl, (4.016) thiophanate-methyl, (4.017) thiophanate-methyl, (4.018) thiophanate-methyl, (4.019) thiophanate-methyl, (4.020) thiophanate-methyl, (4.021) thiophanate-methyl, (4.022) thiophanate-methyl, (4.023) thiophanate-methyl, (4.024) thiophanate-methyl, (4.025) thiophanate-methyl, (4.026) thiophanate-methyl, (4.027) thiophanate-methyl, (4.028) thiophanate-methyl, (4.029) thiophanate-methyl, (4.030) thiophanate-methyl, (4.031) thiophanate-methyl, (4.032) thiophanate-methyl, (4.033) thiophanate-methyl, (4.034) thiophanate-methyl, (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.

[1006] 5) Compounds capable of multi-site action, such as (5.001) Bordeaux mixture, (5.002) Captafol, (5.003) Captan, (5.004) Chlorothalonil, (5.005) Copper hydroxide, (5.006) Copper naphthenate, (5.007) Copper oxide, (5.008) Copper oxychloride, oxychloride), (5.009) copper (2+) sulfate, (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.

[1007] 6) Compounds that can induce host defense, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, and (6.004) tiadinil.

[1008] 7) Inhibitors of amino acid and / or protein biosynthesis, for example, (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

[1009] 8) Inhibitors of ATP production, for example (8.001) silthiofam.

[1010] 9) Inhibitors of cell wall synthesis, for example, (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[1011] 10) Inhibitors of lipid and membrane synthesis, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

[1012] 11) Inhibitors of melanin biosynthesis, for example (11.001) tricyclazole, (11.002) tolprocarb.

[1013] 12) Inhibitors of nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M, kiralaxyl, (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[1014] 13) Inhibitors of signal transduction, for example, (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, and (13.006) vinclozolin.

[1015] 14) Compounds that can act as uncouplers, for example (14.001) fluazinam and (14.002) meptyldinocap.

[1016] 15) Other fungicides, such as (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.0 09) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Flutianil, (15.012) Fosetyl-aluminum, (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) pyr iofenone (chlazafenone), (15.028) isobutylethoxyquinoline (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] -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-methoxy 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) ipflufenoquinol, (1 5.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) fluoxapiprolin, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-phenylphenol and salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) quinofumelin, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dione Hydrogen-1,4-benzoxazepine, (15.055) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.056) (2Z)-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-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate tert-Butyl}pyrimidin-2-yl}carbamate, (15.062) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063) aminopyrifen, (15.064) N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyliminocarboxamide, (15.065) N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide, (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]benzamide 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-carbonimino]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.084) N-[(Z)-N-methoxy-C-methyl-carbonimino]-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]acetamide ] methyl] propionamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propionamide, (15.090) 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091) 1,1-diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, (15.093) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094) 1-methoxy-3-methyl-1-[[4-[5-( 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]propionamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propionamide, (15.098) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide 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) 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylic acid ethyl ester, (15.109) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.111) 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-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115) 1-(5-(fluoromethyl)-6-methyl- pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116) 1-(6-(difluoromethyl)-5-methoxy-pyridin-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}propionamide, (15.119) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidinamide] methanesulfonate 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.

[1017] All named mixing components of groups (1) to (15) described above may be present in the form of free compounds or, if their functional groups are capable of forming salts, in the form of their agriculturally acceptable active salts.

[1018] The compounds of formula (I) and the compositions of the present invention may also be combined with one or more biological control agents.

[1019] As used herein, the term "biological control" 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 biological control agents.

[1020] As used herein, the term "biological control agent" is defined as a non-pest organism and / or a protein or secondary metabolite produced by such an organism for biocontrol purposes. Mutants of a second organism are included within the definition of a biological control agent. The term "mutant" refers to a variant of a parent strain, as well as methods for obtaining a mutant or variant, in which the pesticide activity is greater than the pesticide activity expressed by the parent strain. The "parent strain" herein is defined as the original strain before mutagenesis. To obtain such mutants, the parent strain can be treated with chemicals such as N-methyl-N'-nitro-N-nitrosoguanidine, ethylmethylsulfone, or irradiated with gamma rays, x-rays, or ultraviolet light, or other methods known to those skilled in the art. Known mechanisms of biocontrol agents include enteric bacteria that control root rot by competing for fungal space on the root surface. Bacterial toxins (such as antibiotics) have been used to control pathogens. The toxins can be isolated and applied directly to the plant, or bacterial species can be applied that produce the toxin in situ.

[1021] A "variant" is a strain having all the identifying characteristics of an NRRL or ATCC accession number as set forth herein and can be identified as having a genome that hybridizes under high stringency conditions to the genome of the NRRL or ATCC accession number.

[1022] "Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex that is stabilized by hydrogen bonding between nucleotide residues. Hydrogen bonding can occur by Watson-Crick base pairing, Hoogstein binding, or any other sequence-specific means. The complex can contain two chains forming a double-stranded structure, three or more chains forming a multi-stranded complex, a single self-hybridizing chain, or any combination of these. Hybridization reactions can be performed under different "stringent" conditions. Typically, low stringency hybridization reactions are performed in 10X SSC or a solution of equivalent ionic strength / temperature at about 40°C. Normal stringency hybridizations are typically performed in 6X SSC at about 50°C, while high stringency hybridization reactions are typically performed in 1X SSC at about 60°C.

[1023] Variants of a designated NRRL or ATCC accession number may also be defined as strains having a genomic sequence that is greater than 85%, more preferably greater than 90%, or more preferably greater than 95% identical to the genome of the designated NRRL or ATCC accession number. By "sequence identity" of a polynucleotide or polynucleotide region (or a polypeptide or polypeptide region) to another sequence, a percentage (e.g., 80%, 85%, 90%, or 95%) is meant that, when aligned, the two sequences being compared have that percentage of bases (or amino acids) that are the same. Such alignments and percentages of homology or sequence identity can be determined using software programs known in the art, for example, those described in Current Protocols in Molecular Biology (FM Ausubel et al., eds., 1987).

[1024] NRRL is the abbreviation of Agricultural Research Service Culture Collection. According to the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure, this organization is an international depository institution established for the purpose of depositing microbial strains. Its address is National Center for Agricultural Utilization Research, Agricultural Research service, US Department of Agriculture, 1815 North University Street, Peroira, Illinois 61604 USA.

[1025] ATCC is the abbreviation of American Type Culture Collection. According to the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure, the organization is an international depository established for the purpose of preserving microbial cultures. Its address is ATCC Patent Depository, 10801 University Blvd., Manassas, VA 10110 USA.

[1026] Examples of biological control agents that can be combined with the compounds of formula (I) and the compositions of the present invention are:

[1027] (A) an antibacterial agent selected from the group consisting of:

[1028] (A1) Bacteria, such as (A1.1) Bacillus subtilis, in particular strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL Accession No. B21661, US Patent No. 6,060,051); (A1.2) Bacillus sp., in particular strain D747 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE ), Accession No. FERM BP-8234, U.S. Patent No. 7,094,592; (A1.3) Bacillus pumilus, particularly strain BU F-33, NRRL Accession No. 50185 (available from BASF as (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24, registration number DSM 10271 (available from Novozymes as or ECO (EPA accession 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, (available from BASF SE as PLUS, FLEX and EXTRA); (A1.7) Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (WO 2013 / 034938) from Certis USA LLC (a subsidiary of Mitsui & Co.); (A1.8) Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co.); (A1.9) Paenibacillus polymyxa, in particular strain AC-1 (e.g., from Green Biotech Company Ltd. ); (A1.10) Pseudomonas proradix (e.g. from Sourcon Padena ); (A1.11) Pantoea agglomerans, particularly strain E325 (accession number NRRL B-21856) (available from Northwest Agri Products as BLOOMTIME BIOLOGICAL TM FD BIOPESTICIDE obtained); and

[1029] (A2) Fungi, such as (A2.1) Aureobasidium pullulans, in particular blastospores of strain DSM 14940, blastospores of strain DSM 14941, or a mixture of blastospores of strains DSM 14940 and DSM 14941 (e.g. from bio-ferm, CH and BLOSSOM ); (A2.2) Pseudozyma aphidis (as disclosed by Yissum Research Development Company of the Hebrew University of Jerusalem in WO 2011 / 151819); (A2.3) Saccharomyces cerevisiae, in particular strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938 or CNCM No. 1-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790);

[1030] (B) a biofungicide selected from the group consisting of:

[1031] (B1) bacteria, for example (B1.1) Bacillus subtilis, in particular strain QST713 / AQ713 (available from Bayer CropScience LP, US as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661 and described in US Pat. No. 6,060,051); (B1.2) Bacillus pumilus, in particular strain QST2808 (available from Bayer CropScience LP, US as pumilus, particularly strain GB34 (available from Bayer AG, DE as Yield (B1.4) Bacillus pumilus, in particular strain BU F-33, NRRL registration number 50185 (available from BASF as part of the CARTISSA product line, EPA registration number 71840-19); (B1.5) Bacillus amyloliquefaciens, in particular strain D747 (available from Kumiai Chemical Industry Co., Ltd. as Double Nickel TM (B1.6) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan, with registration number FERM BP-8234 and U.S. Patent No. 7,094,592); WP, registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277); (B1.7) Bacillus subtilis strain MBI 600 (available from BASF SE as SUBTILEX), registration number NRRL B-50595, U.S. Patent No. 5,061,495; (B1.8) Bacillus subtilis strain GB03 (available from Bayer AG, DE as (B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24, registration number DSM 10271 (available from Novozymes as or ECO (EPA accession number 70127-5)); (B1.10) Bacillus mycoides, isolate J, accession number B-30890 (available from Certis USA LLC (a subsidiary of Mitsui & Co.) as BMJ or WG and LifeGard TM(B1.11) Bacillus licheniformis, in particular strain SB3086, accession number ATCC 55406, WO 2003 / 000051 (available from Novozymes as Biofungicides and Green Release 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 as PLUS, FLEX and EXTR); (B1.14) Bacillus subtilis CX-9060 from Certis USA LLC (a subsidiary of Mitsui & Co.); (B1.15) Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL Accession No. B-50768; WO 2014 / 028521) (from Marrone Bio Innovations ); (B1.16) Bacillus amyloliquefaciens strain FZB42, registration number DSM 23117 (available from ABiTEP, DE (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (from FMC (WG) and (WP)); (B1.18) Bacillus mohaiwei strain R3B from Certis USA LLC (a subsidiary of Mitsui & Co.) (accession number NCAIM (P) B001389) (WO 2013 / 034938); (B1.19) Paenibacillus polymyxa plantarum subsp. plantarum from BASF SE (WO 2016 / 020371); (B1.20) Paenibacillus epiphyticus from BASF SE (WO 2016 / 020371); (B.1.21) Pseudomonas chlororaphis strain AFS009, accession number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER from AgBiome Innovations, US TM and ); (B1.22) Pseudomonas chlororaphis, in particular strain MA342 (eg, provided by Bioagri and Koppert and ); (B1.23) Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (from Novozymes and ); (B1.24) Agrobacterium radiobacter strain K84 (e.g., from AgBioChem, CA ); (B1.25) radiobacterium strain K1026 (e.g. NOGALL from BASF SE TM ); (B1.26) Bacillus subtilis KTSB strain (from Donaghys ); (B1.27) Bacillus subtilis IAB / BS03 (AVIV from STK Bio-AgTechnologies TM ); (B1.28) Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan WP, registered as a biofungicide in Taiwan under registration numbers 4764, 5454, 5096, and 5277); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN from the University of Pretoria); TM ); (B1.30) Bacillus methylotrophicus strain BAC-9912 (from Chinese Academy of Sciences' Institute of Applied Ecology); (B1.31) Pseudomonas proradix (e.g. from Sourcon Padena) ); (B1.32) Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (accession number DSM 7206) (from Verdera From BioWorks See Crop Protection 2006, 25, 468-475); (B1.33) Pseudomonas fluorescens strain A506 (e.g. provided by NuFarm );and

[1032] (B2) Fungi, for example: (B2.1) Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM-9660; e.g., from Bayer CropScience Biologics GmbH) ); (B2.2) Metschnikowia fructicola, in particular strain NRRL Y-30752; (B2.3) Microsphaeropsis ochracea; (B2.5) Trichoderma atroviride, in particular strain SC1 (Accession No. CBS122089, WO 2009 / 116106 and U.S. Patent No. 8,431,120 (from Bi-PA)), strain 77B (T77 from Andermatt Biocontrol) or strain LU132 (e.g., Sentinel from Agrimm Technologies Limited); (B2.6) Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert) or strain Cepa Simb-T5 (from Simbiose Agro); (B2.14) Gliocladium roseum (also known as Clonostachys rosea f. rosea), in particular 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 fieldpea, 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. viride), in particular strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); (B2.37) Trichoderma asperellum, in particular strain SKT-1, registration number FERM P-16510 (eg from KumiaiChemical Industry. ), strain T34 (e.g. T34 Biocontrol provided by Biocontrol Technologies S.L., ES) or strain ICC 012 from Isagro; (B2.38) Trichoderma aureum, strain CNCM 1-1237 (e.g. from Agrauxine, FR WP); (B2.39) Trichoderma amurense, strain number V08 / 002387; (B2.40) Trichoderma amurense, strain NMI number V08 / 002388; (B2.41) Trichoderma amurense, strain NMI number V08 / 002389; (B2.42) Trichoderma amurense, strain NMI number V08 / 002390; (B2.43) Trichoderma amurense, strain LC52 (e.g., Tenet provided by Agrimm Technologies Limited); (B2.44) Trichoderma amurense, strain ATCC 20476 (IMI206040); (B2.45) Trichoderma aureum, strain T11 (IMI352941 / CECT20498); (B2.46); Trichodermaharmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g., from Makhteshim, US ); (B2.49) Trichoderma acanthosporum, 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) budding mold, in particular blastospores of strain DSM 14940; (B2.57) budding mold, in particular blastospores of strain DSM 14941; (B2.58) budding mold, in particular a mixture of blastospores of strains DSM 14940 and DSM 14941 (e.g. provided by bio-ferm, CH ); (B2.64) Cladosporium cladosporioides, strain H39, accession number CBS122244, US2010 / 0291039 (provided by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonostachys roseaf.catenulate) strain J1446 (provided by Lallemand, for example). ); (B2.70) conidia of Lecanicillium lecanii (formerly Verticillium lecanii) strain KV01 (e.g. provided by Koppert / Arysta ); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Patent No. 7,579,183; (B2.75) Trichoderma aureum, strain SKT-1 (FERM P-16510), Japanese Patent Publication (Kokai) No. 11-253151A; (B2.76) Trichoderma aureum, strain SKT-2 (FERM P-16511), Japanese Patent Publication (Kokai) No. 11-253151A; (B2.77) Trichoderma aureum, strain SKT-3 (FERM P-17021), Japanese Patent Publication (Kokai) No. 11-253151A; (B2.78) Trichoderma gaimsii gamsii) (formerly T. viride), strain ICC080 (IMICC 392151 CABI, e.g., BioDerma provided by AGROBIOSOL DE MEXICO, SADE CV); (B2.79) Trichoderma harzianum, strain DB 103 (available as T-Gro 7456 from Dagutat Biolab); (B2.80) Trichoderma polysporum, strain IMI 206039 (e.g., Binab TF WP provided by BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum, accession number Ts3550 (e.g., Tricovab provided by CEPLAC, Brazil); (B2.83) Ulocladium oudemansii strain U3, accession number NM 99 / 06216 (e.g., provided by Botry-Zen Ltd, New Zealand); and from BioWorks, Inc. ); (B2.84) Verticillium albo-atrum (formerly V. dahliae), strain WCS850, accession number WCS850, deposited with the Central Bureau for Fungi Cultures (e.g., DUTCH provided by TreeCare Innovations ); (B2.86) Verticillium chlamydosporium; (B2.87) a mixture of Trichoderma aculeatus strain ICC 012 (also known as Trichoderma harzianum ICC012) (accession number CABICC IMI 392716) and Trichoderma gemsii strain (formerly T. viride) strain ICC080 (accession number IMI 392151) (e.g., BIO-TAM from Isagro USA, Inc. TM and provided by Agrobiosol de Mexico, SAde CV ); (B2.88) Trichoderma asperelloides JM41R (registration number NRRL B-50759) (TRICHO from BASF SE ); (B2.89) Aspergillus flavus strain NRRL21882 (from Syngenta / ChemChina known as (B2.90) Chaetomium cupreum (registration number CABI 353812) (e.g., BIOKUPRUM provided by AgriLife TM ); (B2.91) Saccharomyces cerevisiae, in particular strain LASO2 (from Agro-Levures et Dérivés), strain LAS117 cell wall (from Lesaffre from BASF SE ), strains CNCM No. 1-3936, CNCM No. 1-3937, CNCM No. 1-3938, CNCM No. 1-3939 from Lesaffre et Compagnie, FR (WO 2010 / 086790); (B2.92) Trichoderma virens strain G-41, formerly also known as Gliocladium virens (Accession No. ATCC 20906) (e.g., from BioWorks, US PLUS WP and PLUS WP); (B2.93) Trichoderma hamatum, accession number ATCC 28012; (B2.94) Pseudomonas aeruginosa strain AQ10, accession number CNCM I-807 (e.g., AQ provided by IntrachemBio Italia ); (B2.95) Phlebiopsis gigantea strain VRA 1992 (from Danstar Ferment C); (B2.96) Penicillium steckii from BASF SE (DSM 27859; WO 2015 / 067800); (B2.97) Chaetomium globosum (available from Rivale (B2.98) Cryptococcus flavescens, strain 3C (NRRL Y-50378); (B2.99) Dactylaria candida; (B2.100) Dilophosphora alopecuri (can 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 gemsii (formerly T. viride), strain ICC 080 (IMI CC 392151 CABI) (available from AGROBIOSOL DE MEXICO, SADE CV (B2.104) Trichoderma fertile (for example the product TrichoPlus from BASF); (B2.105) Muscodorroseus, in particular strain A3-5 (accession number NRRL 30548); (B2.106) Simplicillium lanosoniveum;

[1033] Biological control agents having the effect of improving plant growth and / or plant health, which can be combined with the compound combination of the present invention, include:

[1034] (C1) Bacteria selected from the group consisting of: Bacillus pumilus, in particular strain QST2808 (NRRL Accession No. B-30087); Bacillus subtilis, in particular strain QST713 / AQ713 (NRRL Accession No. B-21661 and described in U.S. Patent No. 6,060,051; available from Bayer CropScience LP, US OPTI or ASO); Bacillus subtilis, particularly strain AQ30002 (accession number NRRL B-50421 and described in U.S. patent application Ser. No. 13 / 330,576); Bacillus subtilis, particularly strain AQ30004 (NRRL B-50455 and described in U.S. patent application Ser. No. 13 / 330,576); Sinorhizobium meliloti strain NRG-185-1 (from Bayer CropScience GOLD); Bacillus subtilis strain BU1814, (available from BASF SE as Bacillus subtilis rm303 (from Biofilm CropProtection ); Bacillus amyloliquefaciens pm414 (from Biofilm Crop Protection ); 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), Bacillus cereus family member EE128 (NRRL No. B-50917), Bacillus thuringiensis (Bacillus thuringiensis) BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7), Bacillus cereus family member EE349 (NRRL No. B-50928), Bacillus amyloliquefaciens SB3281 (ATCC #PTA-7542; WO2017 / 205258), Bacillus amyloliquefaciens TJ1000 (available from Novozymes as Bacillus firmus, in particular strain CNMC 1-1582 (e.g. from BASF SE ); Bacillus pumilus, in particular strain GB34 (eg YIELD from Bayer Crop Science, DE ); Bacillus amyloliquefaciens, in particular strain IN937a; Bacillus amyloliquefaciens, in particular strain FZB42 (eg from ABiTEP, DE ); Bacillus amyloliquefaciens BS27 (registration number NRRL B-5015); a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as (WG), (WP) obtained); Bacillus cereus, in particular strain BP01 (ATCC 55675; e.g., from Arysta Lifescience, US ); Bacillus subtilis, in particular strain MBI 600 (e.g. from BASF SE ); Bradyrhizobium japonicum (e.g., from Novozymes ); Mesorhizobium cicer (e.g. NODULATOR from BASF SE); Rhizobium leguminosarium biovar viciae (e.g. NODULATOR from BASF SE); Delftia acidovorans, in particular strain RAY209 (e.g. ); Lactobacillus sp. (e.g., from LactoPAFI ); Paenibacillus polymyxa, in particular strain AC-1 (e.g. from Green Biotech Company Ltd. ); Pseudomonas proradix (e.g. from Sourcon Padena ); Azospirillum brasilense (e.g., from KALO, Inc. ); Azospirillum lipoferum (eg, VERTEX-IF from TerraMax, Inc. TM ); a mixture of Azotobacter vinelandii and Clostridium pasteurianum (available from Agrinos viceae strain Z25 (accession number CECT 4585); Azorhizobium caulinodans, in particular strain ZB-SK-5; Azotobacter chroococcum, in particular strain H23; Azotobacter vesicatorii, in particular strain ATCC 12837; Bacillus siamensis, in particular strain KCTC 13613T; Bacillus tequilensis, in particular strain NII-0943; Serratia marcescens, in particular strain SRM (accession number MTCC 8708); Thiobacillus sp. (e.g., from Cropaid Ltd UK );and

[1035] (C2) Fungi selected from the group consisting of: Purpureocillium lilacinum (formerly Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550; e.g. BioAct from Bayer CropScience Biologics GmbH) Penicillium bilaii, strain ATCC 22348 (e.g. BioAct from Acceleron BioAg GmbH) ), Demodex flavus, strain V117b; Trichoderma aureum strain CNCM I-1237 (e.g. from Agrauxine, FR WP), Trichoderma viride, such as strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); Trichoderma amurensis strain LC52 (also known as Trichoderma amurensis strain LU132; for example, Sentinel from Agrimm Technologies Limited); Trichoderma amurensis strain SC1 described in International Application No. PCT / IT2008 / 000196; Trichoderma aculeatus strain kd (for example, T-Gro from Andermatt Biocontrol); Trichoderma aculeatus strain Eco-T (Plant Health Products, ZA); Trichoderma harzianum strain T-22 (for example, Trianum-P from Andermatt Biocontrol or Koppert); Myrothecium verrucaria strain AARC-0255 (for example, DiTera from Valent Biosciences). TM ); Penicillium strain ATCCATCC20851; Pythium oligandrum strain M1 (ATCC 38472; for example, Polyversum from Bioprepraty, CZ); Trichoderma viride strain GL-21 (for example, from Certis, USA ); Verticillium dahliae (formerly V. dahliae) strain WCS850 (CBS276.92; e.g., DutchTrig from Tree Care Innovations); Trichoderma aureum, particularly 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., contained in Myco-Sol from Helena Chemical Company); Rhizopogon fulvigleba (e.g., contained in Myco-Sol from Helena Chemical Company); and Trichoderma virens strain GI-3;

[1036] Insecticidal biological control agents selected from:

[1037] (D1) Bacteria selected from the group consisting of Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372; e.g., from Valent BioSciences ); Bacillus mycoides, isolate J. (e.g., BmJ from Certis USA LLC (a subsidiary of Mitsui & Co.)); Bacillus sphaericus, particularly serotype H5a5b strain 2362 (strain ABTS-1743) (e.g., from Valent BioSciences, US ); Bacillus thuringiensis subsp. kurstaki strain BMP 123 from Becker Microbial Products, IL; Bacillus thuringiensis subsp. kurstaki, particularly serotype H-7 (e.g., from Valent BioSciences, US WG); Bacillus thuringiensis subsp. Kurstaki strain HD-1 (e.g., from Valent BioSciences, US ES); Bacillus thuringiensis subsp. Kurstaki strain BMP 123 provided by Becker Microbial Products, IL; Bacillus thuringiensis israelensis strain BMP 144 (e.g., provided by Becker Microbial Products IL ); Burkholderia spp., in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Accession No. NRRL B-50319; WO 2011 / 106491 and WO 2013 / 032693; for example MBI-206TGAI and ); active purple bacteria (Chromobacterium subtsugae), in particular strain PRAA4-1T (MBI-203; e.g., from Marrone Bio Innovations ); Paenibacillus popilliae (formerly Bacillus popilliae); for example, 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) (eg, provided by Valent BioSciences, US ); Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., from AEF Global ); Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428; e.g., from BioFa DE FC); Bacillus thuringiensis var. japonensis strain Buibui; Bacillus thuringiensis subsp. Kurstaki strain ABTS 351; Bacillus thuringiensis subsp. Kurstaki strain PB 54; Bacillus thuringiensis subsp. Kurstaki strain SA 11; Bacillus thuringiensis subsp. Kurstaki strain SA 12; Bacillus thuringiensis subsp. Kurstaki strain EG 2348; Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC provided by Changzhou Jianghai Chemical Factory); Bacillus thuringiensis subsp. Ayuzawa strain GC-91; Serratia entomophila (e.g., provided by Wrightson Seeds ); Serratia marcescens, in particular strain SRM (accession number MTCC 8708); and Wolbachia pipientis ZAP strain (e.g., ZAP from MosquitoMate );and

[1038] (D2) Fungi selected from the group consisting of 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 No. ATCC 74250; e.g., from Laverlam International Corporation ES and ); Zoophtora radicans; Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073), Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075), and Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074) (WO 2017 / 066094; Pioneer Hi-Bred International); Beauveria bassiana strain ATP02 (accession number DSM 24665). Of these, particularly preferred is Paecilomyces fumosorosus (formerly known as Paecilomyces fumosorosus) strain apopka 97;

[1039] (E) a virus selected from the group consisting of Adoxophyes orana (summer fruit tortrix) granulovirus (GV), Cydia pomonella (codling moth) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, and Spodoptera littoralis (African cotton leafworm) NPV;

[1040] (F) Bacteria and fungi that can be added to plants or plant parts or plant organs as "inoculants" and that, by virtue of their specific properties, promote plant growth and plant health. Examples of such bacteria and fungi are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigasporamonosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp. and Streptomyces spp.; and

[1041] (G) Plant extracts and products formed by microorganisms (including proteins and secondary metabolites) that can be used as biocontrol agents are, for example, Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), pyrethrum / pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem TM "Insecticides", rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, extracts of Brassicaceae (especially rapeseed powder or mustard powder), and biological insecticides / acaricides obtained from olive oil, especially those with a carbon chain length of C 16 -C 20 Unsaturated fats / carboxylic acids as active ingredients, such as, for example, those contained in the trade name products.

[1042] The compounds of formula (I) and the compositions of the present invention may be combined with one or more active ingredients selected from the group consisting of insecticides, acaricides and nematicides.

[1043] "Insecticides" and the term "insecticide" refer to a substance that increases the mortality rate or inhibits the growth rate of insects. As used herein, the term "insects" includes all organisms in the class "Insecta".

[1044] "Nematicide" and "nematicidal" refer to a substance that increases mortality or inhibits the growth rate of nematodes. In general, the term "nematode" encompasses eggs, larvae, juveniles, and mature forms of the organism.

[1045] "Acaricide" and "acaricidal" refer to a substance that increases the mortality or inhibits the growth rate of ectoparasites belonging to the class Arachnida, subclass Acari.

[1046] Examples of insecticides, acaricides and nematicides that can be mixed with the compounds of formula (I) and the compositions of the invention are:

[1047] (1) Acetylcholinesterase (AChE) inhibitors, for example, carbamates, for example, alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, fenamiprid, formetanate), furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb;or organophosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, cyanophos, demeton-S-methyl, diazinon, dichlorvos, chlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, O-(methoxy isopropyl aminothiophosphoryl salicylate, isoxathion, malathion, mecarbam, methidathion, mevinphos, naled, omethoate, oxydemeton-methyl, phenthoate, phorate, phosalone, phosmet, phoxim, pirimiphos-methyl ethyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, tebupirimfos, temephos, tetrachlorvinphos, thiometon-methyl, triazophos, triclorfon, and vamidothion.

[1048] (2) GABA-gated chloride channel blockers, such as cyclopentadienyl-organochlorines, such as chlordane and endosulfan, or phenylpyrazoles (fiproles), such as ethiprole and fipronil.

[1049] (3) Sodium channel modulators, such as pyrethroids, for example, acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β- Cypermethrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox rox), fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1 R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, and transfluthrin, or methoxychlor.

[1050] (4) Competitive modulators of nicotinic acetylcholine receptors (nAChRs), for example neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone.

[1051] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as spinosyns, for example spinetoram and spinosad.

[1052] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, for example, abamectin, emamectin benzoate, lepimectin and milbemectin.

[1053] (7) Juvenile hormone mimetics, such as, for example, juvenile hormone analogues, such as hydroprene, kinoprene and methoprene, or fenoxycarb, or pyriproxyfen.

[1054] (8) Various nonspecific (multisite) inhibitors, such as, for example, alkyl halides, for example, methyl bromide and other alkyl halides; or chloropicrine or sulphuryl fluoride or borax or tartar emetic or methyl isocyanate generators, such as diazomet and metam.

[1055] (9) Chordotonal organ modulators, such as pymetrozine or flonicamid.

[1056] (10) Mite growth inhibitors, such as, for example, clofentezine, hexythiazox and diflovidazin, or etoxazole.

[1057] (11) Insect gut membrane microbial disruptors, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and the following Bt plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1.

[1058] (12) Mitochondrial ATP synthase inhibitors, for example ATP disruptors, such as diafenthiuron; or organotin compounds, such as azocyclotin, cyhexatin and fenbutatinoxide; or propargite, or tetradifon.

[1059] (13) Uncouplers of oxidative phosphorylation by interrupting the proton gradient, such as chlorfenapyr, dinitrocresol (DNOC), and sulfluramid.

[1060] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocylam and thiosultap-sodium.

[1061] (15) Type O chitin biosynthesis inhibitors, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[1062] (16) Type 1 chitin biosynthesis inhibitors, such as buprofezin.

[1063] (17) Molting disruptors (especially for insects of the order Diptera), for example cyromazine.

[1064] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[1065] (19) Octopamine receptor agonists, such as amitraz.

[1066] (20) Mitochondrial complex III electron transport inhibitors, such as hydramethylnone, acequinocyl or fluacrypyrim.

[1067] (21) Mitochondrial complex I electron transport inhibitors, for example METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad, or rotenone (Derris).

[1068] (22) Voltage-dependent sodium channel blockers, such as indoxacarb and metaflumizone.

[1069] (23) Acetyl-CoA carboxylase inhibitors, for example tetronic acid and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[1070] (24) Mitochondrial complex IV electron transport inhibitors, such as phosphines, for example aluminum phosphide and phosphine; or cyanides, for example calcium cyanide, potassium cyanide and sodium cyanide.

[1071] (25) Mitochondrial complex II electron transport inhibitors, for example, β-ketonitrile derivatives, such as cyenopyrafen and cyflumetofen, and carboxanilides, such as pyflubumide.

[1072] (28) Ryanodine receptor modulators, such as diamides, for example chlorantraniliprole, cyantraniliprole and flubendiamide.

[1073] Other active compounds, such as Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclaniliprol e), Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, Epsilon-Metofluthrin, Epsilon-Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexa fon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paicho ngding), Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen, Thiofluoximate, Triflumezopyrim and Iodomethaneiodomethane); also preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), and the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidinyl]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 106457) (CAS 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carbonate (known from EP2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160) (CAS792914-58-0), PF1364 (known from JP2010 / 018586) (CAS1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO2012 / 029672) (CAS1363400-41-2), (3E)-3-[1-[(6-chloro-3- [pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from WO2013 / 144213) (CAS1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010 / 051926) (CAS1226889-14-0), 5-Bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thioheterocyclic) butyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxo-3-thietanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxo-3-thietanyl)benzamide (by WO 2013 / 050317 A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide, (+)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide and (-)-N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propionamide (from WO 2013 / 162715 A2, WO 2013 / 162716A2, US2014 / 0213448A1) (CAS1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (from CN101337937A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012 / 034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from WO 2011 / 085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9); 3-(2,2-dichlorovinyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylate (known from CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose (known from US 2014 / 0275503A1) (CAS1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS1253850-56-4), (8-trans)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-cis)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (from WO 2007040280A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propionamide (known from WO 2015 / 058021 A1, WO 2015 / 058028 A1) (CAS 1477919-27-9) and N-[4-(aminothiomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from WO 2013 / 115391 A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010 / 066780 A1, WO 2011 / 151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO 2014 / 187846 A1) (CAS 1638765-58-8), ethyl 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carbonate (known from WO 2010 / 066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridinium]-2,2,2-trifluoroacetamide (known from DE 3639877 A1, WO2012029672A1) (CAS1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridinyl]-2,2,2-trifluoroacetamide (known from WO 2016005276 A1) (CAS1689566-03-7), [N(Z)]-N-[1-[(6-chloro-3-pyridyl)methyl]-2(1H)-pyridinyl]-2,2,2-trifluoroacetamide (CAS1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from WO 2011 / 105506A1, WO 2016 / 133011 A1) (CAS 1332838-17-1).

[1074] Examples of herbicides that can be mixed with the compounds of formula (I) and the compositions of the invention are:

[1075] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-5-fluoro-6-(7- (1H-indol-6-yl)pyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin , azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclam opyron), bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bixlozone, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, bromoxynil-potassium,Bromoxynil-heptanoate and bromoxynil-octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, chlorpyrifos carfentrazone-ethyl, chloramben, chlorbromuron, 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1,3-dimethyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, chlorfenac, chlorfenac-sodium, oats chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 4-{2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}-1-ethyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazol- 4-carboxylate, chlorophthalimide, chlorotoluron, chlorthal-dimethyl, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop,Clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim m), cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium, 2,4-D-diolamin, 2,4-D-ethyl ester, 2,4-D-2-ethylhexyl ester, 2,4-D-isobutyl ester, 2,4-D-isooctyl ester, 2,4-D-isopropylammonium salt, 2,4-D-potassium salt, 2,4-D-triisopropanolammonium salt and 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl ester, 2,4-DB-dimethylammonium salt, 2,4-DB-isooctyl ester, 2,4-DB-potassium salt and 2,4-DB-sodium salt, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, dichlorprop, dichlorprop rprop-P), diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn,Dimethenamid, dimethenamid-P, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 1,3-dimethyl-4-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat ), diquat-dibromid, dithiopyr, diuron, dihydroxymethylpropionic acid (DMPA), dinitrocresol (DNOC), endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethofumesate ethyl ester (ethiozin), phenoxy}pyridin-2-yl)oxy]ethyl acetate, F-9960, F-5231 (i.e., N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethanesulfonamide), F-7967 (i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6 -(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione), fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl,flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, fluf enpyr), flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, flurenol-dimethylammonium, flurenol-methyl, fluoroglycofen, Fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl et-methyl), fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-sodium, glyphosate, glyphosate-ammonium,Glyphosate-isopropylammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium, H-9201 (O-(2,4-dimethyl-6-nitrophenyl) O-ethylisopropylthioate), halauxifen n), halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methoxyethyl yl), hexazinone, HW-02 (i.e., 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophen-5-yl)methanone, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline- 2,4(1H,3H)-dione, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium,imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, ioxynil-potassium, ioxynil-sodium, triazolam (ipfencarbazone), isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043 (3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole), ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butoxyethyl ester (MCPA-butotyl), MCPA-dimethylammonium salt, MCPA-2-ethylhexyl ester, MCPA-isopropylammonium salt, MCPA-potassium salt and MCPA-sodium salt, MCPB, MCPB-methyl ester, MCPB-ethyl ester and MCPB-sodium salt, 2-methyl-4-chloropropionic acid (mecoprop), 2-methyl-4-chloropropionic acid sodium (mecoprop-sodium) and 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-butotyl), 2-methyl-4-chloropropionic acid (mecoprop-P), 2-methyl-4-chloropropionic acid butoxyethyl ester (mecoprop-P-butotyl), 2-methyl-4-chloropropionic acid dimethyl ester (mecoprop-P-butotyl), 2-methyl-4-chloropropionic acid dimethyl ester (mecoprop-P-butotyl), 2-methyl-4-chloropropionic acid sodium ester (mecoprop-sodium), 2-methyl-4-chloropropionic acid sodium ester (mecoprop-sodium), 2-methyl-4-chloropropionic acid sodium ester (mecoprop-sodium), 2-methyl-4-chloropropionic acid sodium ester (mecoprop- mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl and mecoprop-P-potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam,Metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, 2-({2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)pyridin-3-yl}carbonyl)cyclohexane-1,3-dione, methyl isothiocyanate, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxo-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-ylpropane-1-sulfonate, metobromuron, metolachlor, S-metolachlor or), metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950 (i.e., N-[3-chloro-4-isopropylphenyl]-2-methylpentanamide), NGGC-011, napropamide, NC-310 (i.e., [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)methanone), neburon, nicosulfuron, nonanoic acid acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, mineral oil, phenmedipham,Picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, and propazine (propazine), propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotol e), pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid ), pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P,Quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM-201, QYR-301, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron methyl -methyl), sulfosulfuron, SYN-523, SYP-249 (i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate), SYP-300 (i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioximidazolidine-4,5-dione), 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tefurone (tembotrione), tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, tetflupyrolimet, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl (t trifensulfuron-methyl), thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine,Trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, ZJ-0862 (i.e., 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline).

[1076] Examples of plant growth regulators are:

[1077] acibenzolar, benzothiadiazole, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolid, catechine, chlormequatchloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, endothal-disodium, and mono(N,N-dimethylalkylammonium)endothal, ethephon, flumetralin, fenfluramine, butyl fluorenol, flurprimidol, forchlorfenuron, gibberellic acid acid), inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, paclobutrazol, N-(2-phenylethyl)-β-aminopropionic acid, N-phenylphthalamic acid acid), prohexadione, prohexadione calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, and uniconazole-P.

[1078] Examples of safeners that can be mixed with the compounds of formula (I) and the compositions of the invention are: for example benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, dichlormethane, fenthiophene, fenthiophene-1-oxazolidinone ... Isoxadifen(-ethyl), mefenpyr(-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[1079] Examples of nitration inhibitors that can be mixed with the compounds of formula (I) and the compositions of the present invention are selected from the group consisting of: 2-(3,4-dimethyl-1H-pyrazol-1-yl)succinic acid, 2-(4,5-dimethyl-1H-pyrazol-1-yl)succinic acid, 3,4-dimethyl pyrazolium glycolate, 3,4-dimethyl pyrazolium citrate, 3,4-dimethyl pyrazolium lactate, 3,4-dimethyl pyrazolium mandelate, 1,2,4-triazole, 4-chloro-3-methylpyrazole, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)acetamide, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)formamide, N-((3(5),4-dimethylpyrazol-1-yl)methyl)formamide, N-((4-chloro-3(5)-methyl-pyrazol-1-yl)methyl)formamide; reaction adducts of dicyandiamide, urea and formaldehyde, triazolyl-formaldehyde-dicyandiamide adduct, 2-cyano-1-((4-oxo-1,3,5-triazinane (azinan)-1-yl)methyl)guanidine, 1-((2-cyanoguanidino)methyl)urea, 2-cyano-1-((2-cyanoguanidino)methyl) Guanidine, 2-chloro-6-(trichloromethyl)-pyridine (nitrapyrin or N-serve), dicyandiamide, 3,4-dimethylpyrazole phosphate, 4,5-dimethylpyrazole phosphate, 3,4-dimethylpyrazole, 4,5-dimethylpyrazole, ammonium thiosulfate, neem, neem-based products, linoleic acid, alpha-linolenic acid, methyl p-coumarate, methyl ferulate, methyl 3-(4-hydroxyphenyl)propionate, psanthin, brachialacton, p-benzoquinone sorgoleone, 4-amino -1,2,4-triazole hydrochloride, 1-amino-2-thiourea, 2-amino-4-chloro-6-methylpyrimidine, 2-mercapto-benzothiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (terrazole, etridiazole), 2-sulfanilamidothiazole, 3-methylpyrazole, 1,2,4-triazolethiourea, cyanamide, zeolite powder, catechol, benzoquinone, sodium tetraborate, allylthiourea, chlorate and zinc sulfate.

[1080] The compounds of formula (I) and compositions of the present invention may be combined with one or more agriculturally beneficial agents.

[1081] Examples of agriculturally beneficial agents include biostimulants, plant growth regulators, plant signaling molecules, growth promoters, microbial stimulating molecules, biomolecules, soil conditioners, nutrients, plant nutrition enhancers, such as lipo-chitooligosaccharides (LCO), chitooligosaccharides (CO), chitin compounds, flavonoids, jasmonic acid or its derivatives (e.g., jasmonates), cytokinins, plant growth hormones, gibberellins, abscisic acid, ethylene, brassinolide, salicylates, macro- and micronutrients, linoleic acid or its derivatives, linolenic acid or its derivatives, karrikins, and beneficial microorganisms (e.g., Rhizobium spp., Bradyrhizobium spp., Sinorhizobium spp., Azorhizobium spp., Glomus spp., Macrospora spp., Hymenoscyphous spp., Oidiodendron spp., Lacerta spp., Pisolithus spp., etc. spp.), Psoralea spp., Scleroderma spp., Rhizoctonia spp., Acinetobacter spp., Arthrobacter spp., Arthrobotrys spp., Aspergillus spp., Azospirillum spp., Bacillus spp., Burkholderia spp., Candida spp., Chryseomonas spp., Enterobacter spp., Eupenicillium spp., Exiguobacterium spp., Klebsiella spp., Kluyvera spp., Microbacterium spp., Mucor spp. spp.), Paecilomyces spp., Paenibacillus spp., Penicillium spp., Pseudomonas spp., Serratia spp., Stenotrophomonas spp., Streptomyces spp., Swaminathania spp., Thiobacillus spp., Torulospora spp., Vibrio spp., Xanthobacter spp.), Xanthomonas spp., etc.), and combinations thereof.

[1082] Methods and uses

[1083] The compounds of formula (I) and compositions of the present invention have potential microbicidal activity and / or plant defense regulation potential. They can be used to prevent and treat unwanted microorganisms on plants, such as unwanted fungi and bacteria. In particular, they are used for crop protection (they prevent and treat the microorganisms that bring diseases to plants) or for protecting materials (such as industrial materials, timber, stored goods) described in more detail below. More specifically, the compounds of formula (I) and compositions of the present invention can be used to protect seeds, germinating seeds, newly emerging seedlings, plants, plant parts, fruits, articles gathered and / or plant growth in the soil therein from the invasion and attack of unwanted microorganisms.

[1084] Described in this article Prevention and treatment (Control or controlling) includes preventive treatment, therapeutic treatment and eradication of unwanted microorganisms. Unwanted microorganisms It may be a pathogenic bacterium, a pathogenic virus, a pathogenic oomycete or a pathogenic fungus, more specifically a phytopathogenic bacterium, a phytopathogenic virus, a phytopathogenic oomycete or a phytopathogenic fungus. As described in detail below, these phytopathogenic microorganisms are the causative agents of a wide spectrum of plant diseases.

[1085] More specifically, the compounds of formula (I) and the compositions according to the invention can be used as fungicides. For the purposes of the present invention, the term "fungicide" refers to compounds or compositions which can be used in crop protection to control unwanted fungi and / or to control oomycetes, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

[1086] The compounds of formula (I) and the compositions of the present invention can also be used as antibacterial agents. In particular, they can be used in crop protection, for example to control unwanted bacteria, such as Pseudomonadaceae, Rhizobiaceae, Xanthomonadaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

[1087] The compounds of the formula (I) and the compositions according to the invention can also be used as antiviral agents in crop protection. For example, the compounds of formula (I) and the compositions of the present invention can have an effect on diseases caused by plant viruses, such as tobacco mosaic virus (TMV), tobacco rattle virus, tobacco stunt virus (TStuV), tobacco leaf curl virus (VLCV), tobacco mosaic virus (TVBMV), tobacco necrotic dwarf virus (TNDV), tobacco streak virus (TSV), potato virus X (PVX), potato viruses Y, S, M and A, potato acuba mosaic virus (PAMV), potato mop-top virus (PMTV), potato leaf-roll virus (PLRV), alfalfa mosaic virus ( virus (AMV), cucumber mosaic virus (CMV), cucumber green mottle mosaic virus (CGMMV), cucumber yellows virus (CuYV), watermelon mosaic virus (WMV), tomato spotted wilt virus (TSWV), tomato ringspot virus (TomRSV), sugarcane mosaic virus (SCMV), rice dwarf virus, rice stripe virus, rice black-streaked drawf virus, strawberry mottle virus (SMoV), strawberry vein banding virus (SVBV), strawberry mild yellow edge virus (yellow edge virus (SMYEV), strawberry crinkle virus (SCrV), broad bean wilt virus (BBWV), and melon necrotic spot virus (MNSV).

[1088] The present invention also relates to a method for controlling unwanted microorganisms on plants (such as unwanted fungi, oomycetes and bacteria), which comprises the step of applying at least one compound of formula (I) or at least one composition according to the invention to the microorganisms and / or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants are growing).

[1089] In general, when the compounds of formula (I) and the compositions of the invention are used in a therapeutic or protective method for controlling phytopathogenic fungi and / or phytopathogenic oomycetes, they are applied in an effective and phytocompatible amount to the plants, plant parts, fruits, seeds or to the soil or substrate in which the plants are growing. Suitable substrates for cultivating plants include inorganic-based substrates, such as mineral wool, in particular rock wool, perlite, sand or gravel; organic substrates, such as peat, pine bark or sawdust; and petroleum-based substrates, such as polymer foams or plastic beads. Effective and plant-compatible amount By "amount" is meant an amount sufficient to control or destroy fungi present or susceptible to development on agricultural land without causing any significant symptoms of phytotoxicity to the crop. This amount can vary widely, depending on the fungi to be controlled, the type of crop, the growth stage of the crop, climatic conditions, and the individual compounds or compositions of the invention used. This amount can be determined by systematic field trials and is within the capabilities of those skilled in the art.

[1090] Plants and plant parts

[1091] The compounds of formula (I) and the compositions of the invention can be applied to any plant or plant part.

[1092] plant This refers to all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnology and genetic engineering methods or a combination of these methods, including genetically modified plants (GMO or transgenic plants) and plant cultivars which are or are not protectable by plant breeders' rights.

[1093] Plant cultivarsIt is understood to mean plants having novel properties ("traits") which have been obtained by conventional breeding, mutagenesis or recombinant DNA techniques. These may be cultivars, varieties, biotypes or genotypes.

[1094] Plant parts It is to be understood as meaning all parts and organs of a plant, both above and below ground, such as buds, leaves, needles, stems, trunks, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Plant parts also include harvested material and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, divisions and seeds.

[1095] Plants that can be treated according to the methods described herein include the following: cotton, flax, grapevines, fruits, vegetables, such as Rosaceae sp. (e.g., pome fruits such as apples and pears, and stone fruits such as apricots, cherries, almonds and peaches, and small fruit such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g., banana trees and banana plantations), Rubiaceae sp. (e.g., coffee), Theaceae sp., Sterculiaceae sp. sp.), Rutaceae sp. (e.g., lemon, orange, and grapefruit), Solanaceae sp. (e.g., tomato), Liliaceae sp., Asteraceae sp. (e.g., lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (e.g., cucumber), Alliaceae sp. (e.g., leek, onion), Papilionaceae sp. (e.g., pea); major crop plants, such as Gramineae sp. (e.g., corn, turf grass, cereals (e.g., wheat, rye, rice, barley, oats, millet, and triticale)), Asteraceae sp. (e.g., sunflower), Brassicaceae sp. sp.) (e.g., white cabbage, red cabbage, Brussels sprouts, cauliflower, Brussels sprouts, pakchoi, kohlrabi, radish, as well as rapeseed, mustard, horseradish, and watercress), Fabacae sp. (e.g., beans, peanuts), Papilionaceae sp. (e.g., soybeans), Solanaceae sp. (e.g., potatoes), Chenopodiaceae sp.) (e.g. sugar beet, fodder beet, Swiss chard, beetroot); useful and ornamental plants of gardens and forests; and genetically modified varieties of these plants.

[1096] Plants and plant cultivars which can be treated by the methods disclosed above include plants and plant cultivars which are resistant to one or more biotic stresses, i.e. which plants are better protected against animal or microbial pests, such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

[1097] Plants and plant cultivars that can be treated by the methods disclosed above include those that are resistant to one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, low temperature exposure, heat exposure, osmotic stress, waterlogging, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited nitrogen nutrient availability, limited phosphorus nutrient availability, and shade avoidance.

[1098] Plants and plant cultivars that can be processed by the above-mentioned disclosed method include those plants characterized by the yield characteristics of improvement. The yield that improves in the described plant can be the result of following factors: for example, improved plant physiological function, growth and development, such as water use efficiency, water holding efficiency, improved nitrogen utilization rate, enhanced carbon assimilation, improved photosynthesis, improved germination rate and accelerated maturity. Productivity can also be subject to the impact (under stress and non-stress conditions) of improved plant architecture (plant architecture), which includes but is not limited to: early flowering, flowering control of hybrid seed production, rice seedling vigor, plant size, internode number and internode distance, root growth, seed size, fruit size, pod size, pod number or ear number, seed quantity of each pod or ear, seed quality, enhanced seed fullness, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Other yield traits include seed composition, such as carbohydrate content and composition, for example cotton or starch, protein content, oil content and composition, nutritional value, anti-nutritional compounds reduction, improved processability and better storage stability.

[1099] Plants and plant cultivars that may be treated by the methods disclosed above include plants and plant cultivars that are hybrid plants that already express the characteristic of heterosis or hybrid vigour, which generally results in higher yield, vigour, health and resistance to biotic and abiotic stresses.

[1100] Transgenic plants, seed treatments, and integrated lines (event)

[1101] The compound of formula (I) can be advantageously used to treat transgenic plants, plant cultivars or plant parts that have received genetic material that imparts favorable and / or useful properties (traits) to these plants, plant cultivars or plant parts. Therefore, it is contemplated that the present invention may be combined with one or more recombinant traits or transgenic lines (transgenic event) or a combination thereof. For the purposes of this application, transgenic lines are produced by inserting specific recombinant DNA molecules into specific locations (sites) of plant genome chromosomes. The insertion creates a new DNA sequence known as a "line", characterized in that the inserted recombinant DNA molecules and a certain amount of genomic DNA are adjacent to / flanked by the two ends of the inserted DNA. Such traits or transgenic lines include, but are not limited to, resistance to pests and diseases, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production and herbicide tolerance, wherein the trait is determined relative to a plant lacking such a trait or transgenic line. Specific examples of such advantageous and / or useful properties (traits) are better plant growth, vigor, stress tolerance, stand growth ability, lodging resistance, nutrient uptake, plant nutrition and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity levels, enhanced flowering performance, easier harvesting, accelerated ripening, higher yield, higher quality and / or higher nutritional value of the harvested product, better storage life and / or processability of the harvested product, and increased resistance to animal and microbial pests (e.g. insects, arachnids, nematodes, mites, slugs and snails).

[1102] Among the DNA sequences encoding proteins that confer tolerance properties on these animal and microbial pests (particularly insects), mention may be made in particular of the genetic material encoding the Bt protein from Bacillus thuringiensis, which is widely described in the literature and is well known to those skilled in the art. Mention may also be made of proteins extracted from bacteria such as Photorhabdus (WO 97 / 17432 and WO 98 / 08932). In particular, mention will be made of Bt Cry or VIP proteins including Cry1A, Cry1Ab, Cry1Ac, CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF proteins or toxic fragments thereof, as well as hybrids or combinations thereof, in particular Cry1F protein or hybrids derived from Cry1F protein (such as hybrid Cry1A-Cry1F protein or toxic fragments thereof), Cry1A-type proteins or toxic fragments thereof, preferably Cry1Ac protein or hybrids derived from Cry1Ac protein (such as hybrid Cry1Ab-Cry1Ac protein) or Cry1Ab or Bt2 protein or toxic fragments thereof, Cry2Ae, Cry2Af or Cry2Ag protein or toxic fragments thereof, Cry1A.105 protein or toxic fragments thereof, VIP3Aa19 protein, VIP3Aa20 protein, VIP3A protein produced in COT202 or COT203 cotton lines, as described in Estruch et al. (1996), Proc Natl Acad Sci US A. 28; 93 (11): 5389-94 or a toxic fragment thereof, a Cry protein described in WO 2001 / 47952, an insecticidal protein from a strain of Xenorhabdus (such as described in WO 98 / 50427), Serratia (especially from S. entomophila) or Photorhabdus species, for example, the Tc protein from Photorhabdus described in WO 98 / 08932. In addition, the present invention also includes any variant or mutant of any of the above-mentioned proteins that differs from any of the above-mentioned sequences (especially the sequences of their toxic fragments) in some amino acids (1-10, preferably 1-5), or any variant or mutant of the above-mentioned proteins fused with a transit peptide (such as a plastid transit peptide) or another protein or peptide.

[1103] Another and particularly emphasized example of such a property is the conferring of tolerance to one or more herbicides, such as imidazolinones, sulfonylureas, glyphosate or glufosinate. Among the DNA sequences encoding proteins that confer tolerance to certain herbicides on transformed plant cells and plants, mention may be made of the bar or PAT genes or the Streptomyces coelicolor gene described in WO 2009 / 152359 that confer tolerance to the glufosinate herbicide, suitable EPSPS (5-enolpyruvylshikimate-3-phosphate-synthase) genes that confer tolerance to herbicides targeting EPSPS, in particular to herbicides such as glyphosate and its salts, genes encoding glyphosate-n-acetyltransferase, or genes encoding glyphosate oxidoreductase. Other suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., WO 2007 / 024782), a mutated Arabidopsis ALS / AHAS gene (e.g., U.S. Pat. No. 6,855,533), a gene encoding a 2,4-D-monooxygenase conferring tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), a gene encoding a Dicamba monooxygenase conferring tolerance to Dicamba (3,6-dichloro-2-methoxybenzoic acid).

[1104] Yet another example of such a property is resistance to one or more phytopathogenic fungi, such as Asian Soybean Rust. Among the DNA sequences encoding proteins conferring resistance to such diseases, mention will in particular be made of genetic material from Glycine tomentella, such as any of the publicly available accession series described in WO 2019 / 103918: PI441001, PI483224, PI583970, PI446958, PI499939, PI505220, PI499933, PI441008, PI505256 or PI446961.

[1105] Further and particularly emphasized examples of such traits are increased resistance to bacteria and / or viruses due to, for example, systemic acquired resistance (SAR), systemin, phytoalexins, inducers and resistance genes and correspondingly expressed proteins and toxins.

[1106] Particularly useful transgenic lines among the transgenic plants or plant cultivars that can be preferentially treated according to the present invention include line 531 / PV-GHBK04 (cotton, insect control, described in WO 2002 / 040677), line 1143-14A (cotton, insect control, not deposited, described in WO 2006 / 128569); line 1143-51B (cotton, insect control, not deposited, described in WO 2006 / 128570); line 1445 (cotton, herbicide tolerance, not deposited, described in US-A 2002-120964 or WO2002 / 034946); Line 17053 (rice, herbicide tolerant, deposited as PTA-9843, described in WO2010 / 117737); Line 17314 (rice, herbicide tolerant, deposited as PTA-9844, described in WO2010 / 117735); Line 281-24-236 (cotton, insect control-herbicide tolerant, deposited as PTA-6233 2005 / 103266 or US-A2005-216969); Line 3006-210-23 (cotton, insect control - herbicide tolerance, deposited as PTA-6233, recorded in US-A2007-143876 or WO2005 / 103266); Line 3272 (maize, quality traits, deposited as PTA-9972, recorded in WO2006 / 098952 or US-A 2006-230473); Line 33391 (wheat, herbicide tolerant, deposited as PTA-2347, described in WO 2002 / 027004), Line 40416 (maize, insect control-herbicide tolerant, deposited as ATCC PTA-11508, described in WO 11 / 075593); Line 43A47 (maize, insect control-herbicide tolerant, deposited as ATCC PTA-11509, described in WO 2011 / 075595); Line 5307 (maize, insect control, deposited as ATCC PTA-9561, described in WO 2010 / 077816); Line ASR-368 (bent grass, herbicide tolerant, deposited as ATCC PTA-4816, described in US-A 2006-162007 or WO2004 / 053062); Line B16 (maize, herbicide tolerant, not deposited, described in US-A 2003-126634); Line BPS-CV127-9 (soybean, herbicide tolerant, deposited as NCIMB No. 41603, described in WO2010 / 080829); Line BLR1 (rapeseed, restored male sterility, deposited as NCIMB No. 41193, described in WO2005 / 074671); Line CE43-67B (cotton,insect control, deposited as DSMACC2724, described in US-A 2009-217423 or WO 2006 / 128573); Line CE44-69D (cotton, insect control, not deposited, described in US-A 2010-0024077); Line CE44-69D (cotton, insect control, not deposited, described in WO 2006 / 128571); Line CE46-02A (cotton, insect control, not deposited, described in WO 2006 / 128572); Line COT102 (cotton, insect control, not deposited, described in US-A 2006-130175 or WO 2004 / 039986); Line COT202 (cotton, insect control, not deposited, described in US-A 2007-067868 or WO2005 / 054479); line COT203 (cotton, insect control, not deposited, described in WO2005 / 054480); line DAS21606-3 / 1606 (soybean, herbicide tolerant, deposited as PTA-11028, described in WO2012 / 033794); line DAS40278 (corn, herbicide tolerant, deposited as ATCC PTA-10244 deposited, described in WO2011 / 022469); line DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerant, deposited as PTA-11336, described in WO2012 / 075426), line DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide tolerant, deposited as PTA-11335, described in WO2012 / 075429), line DAS-59122-7 (corn, insect control - herbicide tolerant, deposited as ATCC PTA 11384, described in US-A 2006-070139); line DAS-59132 (maize, insect control-herbicide tolerance, not deposited, described in WO 2009 / 100188); line DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in WO 2011 / 066384 or WO 2011 / 066360); line DP-098140-6 (maize, herbicide tolerance, deposited as ATCC PTA-8296, described in US-A 2009-137395 or WO 08 / 112019); line DP-305423-1 (soybean, quality traits, not deposited, described in US-A 2008-312082 or WO2008 / 054747); line DP-32138-1 (maize, hybrid system, deposited as ATCC PTA-9158,Described in US-A 2009-0210970 or WO 2009 / 103049); Line DP-356043-5 (soybean, herbicide tolerant, deposited as ATCC PTA-8287, described in US-A 2010-0184079 or WO 2008 / 002872); Line EE-1 (eggplant, insect control, not deposited, described in WO 07 / 091277); Line Fil17 (maize, herbicide tolerant, deposited as ATCC 209031, described in US-A 2006-059581 or WO 98 / 044140); line FG72 (soybean, herbicide tolerant, deposited as PTA-11041, described in WO 2011 / 063413), line GA21 (maize, herbicide tolerant, deposited as ATCC 209033, described in US-A 2005-086719 or WO 98 / 044140); line GG25 (maize, herbicide tolerant, deposited as ATCC 209032, described in US-A 2005-188434 or WO 98 / 044140); line GHB119 (cotton, insect control-herbicide tolerant, deposited as ATCC PTA-8398, described in WO 2008 / 151780); line GHB614 (cotton, herbicide tolerant, deposited as ATCC PTA-6878 deposited, described in US-A 2010-050282 or WO 2007 / 017186); line GJ11 (maize, herbicide tolerant, deposited as ATCC 209030, described in US-A 2005-188434 or WO 98 / 044140); line GM RZ13 (sugar beet, virus resistant, deposited as NCIMB-41601, described in WO 2010 / 076212); line H7-1 (sugar beet, herbicide tolerant, deposited as NCIMB 41158 or NCIMB 41159, described in US-A 2004-172669 or WO 2004 / 074492); line JOPLIN1 (wheat, disease resistant, not deposited, described in US-A 2008-064032); Line LL27 (soybean, herbicide tolerant, deposited as NCIMB 41658, described in WO 2006 / 108674 or US-A 2008-320616); Line LL55 (soybean, herbicide tolerant, deposited as NCIMB 41660, described in WO 2006 / 108675 or US-A 2008-196127); Line LLcotton25 (cotton, herbicide tolerant, deposited as ATCC PTA-3343,2003 / 013224 or US A2003-097687); Line LLRICE06 (rice, herbicide tolerance, deposited as ATCC 203353, described in US 6,468,747 or WO2000 / 026345); Line LLRICE62 (rice, herbicide tolerance, deposited as ATCC 203352, described in WO2000 / 026345), Line LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US-A2008-2289060 or WO2000 / 026356); Line LY038 (maize, quality traits, deposited as ATCC PTA-5623 deposited, described in US-A 2007-028322 or WO 2005 / 061720); line MIR162 (corn, insect control, deposited as PTA-8166, described in US-A 2009-300784 or WO 2007 / 142840); line MIR604 (corn, insect control, not deposited, described in US-A 2008-167456 or WO 2005 / 103301); line MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US-A 2004-250317 or WO 2002 / 100163); line MON810 (corn, insect control, not deposited, described in US-A 2002-102582); line MON863 (maize, insect control, deposited as ATCC PTA-2605, described in WO 2004 / 011601 or US-A 2006-095986); line MON87427 (maize, pollination control, deposited as ATCC PTA-7899, described in WO 2011 / 062904); line MON87460 (maize, stress resistance, deposited as ATCC PTA-8910, described in WO 2009 / 111263 or US-A 2011-0138504); line MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US-A 2009-130071 or WO2009 / 064652); line MON87705 (soybean, quality trait - herbicide tolerance, deposited as ATCC PTA-9241, described in US-A 2010-0080887 or WO2010 / 037016); line MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in WO2011 / 034704); line MON87712 (soybean, yield, deposited as PTA-10296, described in WO2012 / 051199),Line MON87754 (soybean, quality traits, deposited as ATCC PTA-9385, described in WO2010 / 024976); Line MON87769 (soybean, quality traits, deposited as ATCC PTA-8911, described in US-A 2011-0067141 or WO2009 / 102873); Line MON88017 (corn, insect control-herbicide tolerance, deposited as ATCC PTA-5582, described in US-A 2008-028482 or WO2005 / 059103); Line MON88913 (cotton, herbicide tolerance, deposited as ATCC PTA-4854, described in WO2004 / 072235 or US-A 2006-059590); line MON88302 (rapeseed, herbicide tolerant, deposited as PTA-10955, described in WO2011 / 153186), line MON88701 (cotton, herbicide tolerant, deposited as PTA-11754, described in WO2012 / 134808), line MON89034 (corn, insect control, deposited as ATCC PTA-7455, described in WO 07 / 140256 or US-A 2008-260932); line MON89788 (soybean, herbicide tolerant, deposited as ATCC PTA-6708, described in US-A 2006-282915 or WO2006 / 130436); line MS1 1 (oilseed rape, pollination control-herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in WO 2001 / 031042); line MS8 (oilseed rape, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in WO 2001 / 041558 or US-A 2003-188347); line NK603 (maize, herbicide tolerance, deposited as ATCC PTA-2478, described in US-A 2007-292854); line PE-7 (rice, insect control, not deposited, described in WO 2008 / 114282); line RF3 (oilseed rape, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in WO 2001 / 041558 or US-A 2003-188347); line RT73 (rapeseed, herbicide tolerant, not deposited, described in WO 2002 / 036831 or US-A 2008-070260); line SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerant, deposited as PTA-11226, described in WO 2012 / 082548); line T227-1 (sugar beet, herbicide tolerant, not deposited,2002 / 44407 or US-A2009-265817); Line T25 (corn, herbicide tolerant, not deposited, described in US-A2001-029014 or WO2001 / 051654); Line T304-40 (cotton, insect control-herbicide tolerant, deposited as ATCC PTA-8171, described in US-A 2010-077501 or WO2008 / 122406); Line T342-142 (cotton, insect control, not deposited, described in WO2006 / 128568); Line TC1507 (corn, insect control-herbicide tolerant, not deposited, described in US-A 2005-039226 or WO2004 / 099447); line VIP1034 (maize, insect control-herbicide tolerant, deposited as ATCC PTA-3925, described in WO2003 / 052073), line 32316 (maize, insect control-herbicide tolerant, deposited as PTA-11507, described in WO2011 / 084632), line 4114 (maize, insect control-herbicide tolerant, deposited as PTA-11506, described in WO2011 / 084621), optionally with line EE-GM1 / LL27 or line EE-GM2 / LL55 (WO2011 / 063413A2) stacked line EE-GM3 / FG72 (soybean, herbicide tolerant, ATCC accession number PTA-11041), line DAS-68416-4 (soybean, herbicide tolerant, ATCC accession number PTA-10442, WO2011 / 066360A1), line DAS-68416-4 (soybean, herbicide tolerant, ATCC accession number PTA-10442, WO2011 / 066384 A1), line DP-040416-8 (corn, insect control, ATCC accession number PTA-11508, WO2011 / 075593A1), line DP-043A47-3 (corn, insect control, ATCC accession number PTA-11509, WO2011 / 075595A1), line DP-004114-3 (corn, insect control, ATCC accession number PTA-11506, WO2011 / 084621A1) , strain DP-032316-8 (corn, insect control, ATCC accession number PTA-11507, WO2011 / 084632A1), strain MON-88302-9 (rape, herbicide tolerance, ATCC accession number PTA-10955, WO2011 / 153186A1), strain DAS-21606-3 (soybean, herbicide tolerance, ATCC accession number PTA-11028, WO2012 / 033794A2),Line MON-87712-4 (soybean, quality traits, ATCC Accession No. PTA-10296, WO2012 / 051199A2), line DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Accession No. PTA-11336, WO2012 / 075426A1), line DAS-14536-7 (soybean, stacked herbicide tolerance, ATCC Accession No. PTA-11335, WO2012 / 075429 A1), line SYN-000H2-5 (soybean, herbicide tolerance, ATCC accession number PTA-11226, WO2012 / 082548A2), line DP-061061-7 (rape, herbicide tolerance, no available deposit number, WO2012071039A1), line DP-073496-4 (rape, herbicide tolerance, no available deposit number, US2012131692), line 8264.44.06.1 (soybean, superimposed herbicide herbicide tolerance, accession number PTA-11336, WO2012075426A2), line 8291.45.36.2 (soybean, stacked herbicide tolerance, accession number PTA-11335, WO2012075429A2), line SYHT0H2 (soybean, ATCC accession number PTA-11226, WO2012 / 082548A2), line MON88701 (cotton, ATCC accession number PTA-11754, WO2012075429A2). 12 / 134808A1), line KK179-2 (alfalfa, ATCC accession number PTA-11833, WO2013 / 003558A1), line pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC accession number PTA-11993, WO2013 / 010094A1), line MZDT09Y (corn, ATCC accession number PTA-13025, WO2013 / 012775A1).

[1107] In addition, the United States Department of Agriculture (USDA) Animal and Plant Health Inspection Service (APHIS) provides a list of such transgenic lines, which can be found on the Internet on their website. aphis.usda.gov Found. For the purposes of this application, the status of this listing as of the filing date of this application is relevant.

[1108] Genes / lines conferring desired traits can also be present in transgenic plants in combination with one another. Examples of transgenic plants that may be mentioned are important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and fruit plants (including apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco and rapeseed. Traits that are particularly emphasized are increased resistance of the plants to insects, arachnids, nematodes, slugs and snails, as well as increased resistance of the plants to one or more herbicides.

[1109] Commercially available examples of such plants, plant parts or plant seeds which may be preferentially treated according to the invention include RIB ROUNDUP VT DOUBLE VT TRIPLE BOLLGARD ROUNDUP READY 2 ROUNDUP 2XTEN DTM INTACTA RR2 VISTIVE and / or XTENDFLEX TM A commercially available product, such as plant seeds, sold or distributed under a trade name.

[1110] pathogens

[1111] Non-limiting examples of pathogens of fungal diseases that can be treated according to the present invention include:

[1112] Diseases caused by powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinulanecator;

[1113] Diseases caused by rust pathogens, such as Gymnosporangium species, such as Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as Puccinia recondita, Puccinia graminis or Puccinia striiformis; Uromyces species, such as Uromyces appendiculatus;

[1114] Diseases caused by pathogens from the oomycetes, such as Albugo species, for example Algubo candida; Bremia species, such as Bremia lactucae; Peronospora species, such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans; Plasmopara species, such as Plasmopara viticola; Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, such as Pythium ultimum. ultimum);

[1115] Leaf spot and leaf wilt diseases caused by pathogens such as Alternaria species, such as Alternaria solani; Cercospora species, such as Cercospora beticola; Cladiosporum species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, such as Colletotrichum spp. lindemuthanium; Corynespora species, such as Corynespora cassiicola; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia spp. bidwelli); Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea; Microdochium species, such as Microdochium nivale; Mycosphaerella species, such as Mycosphaerella graminicola, Mycosphaerella arachidicola, and Mycosphaerella fijiensis;Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophora species, such as Pyrenophora teres and Pyrenophora tritici repentis; Ramularia species, such as Ramularia collo-cygni and Ramularia areola; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii and Septorialycopersii; Stagonospora species, such as Stagonospora nodorum; Typhula species, such as Typhula spp. incarnata); Venturia species, such as Venturia inaequalis;

[1116] Root and stem diseases caused by pathogens such as Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis; Plasmodiophora species, for example Plasmodiophora brassicae; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium species, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; species of the genus Thielaviopsis, for example, Thielaviopsis basicola;

[1117] Diseases of the spadix or panicle (including corn cobs) caused by pathogens such as Alternaria spp., for example Alternaria spp.; Aspergillus spp., for example Aspergillus flavus; Cladosporium spp., for example Cladosporium cladosporioides; Claviceps spp., for example Claviceps purpurea; Fusarium spp., for example Fusarium culmorum; Gibberella spp., for example Gibberella zeae; Monographella spp., for example Monographella nivalis; Stagonospora spp., for example Stagonospora nodorum;

[1118] Diseases caused by smut fungi, such as: Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries or Tilletia controversa; Urocystis species, such as Urocystis occulta; Ustilago species, such as Ustilago nuda;

[1119] Fruit rot caused by pathogens such as Aspergillus spp., such as Aspergillus flavus; Botrytis spp., such as Botrytis cinerea; Monilinia spp., such as Monilinia laxa; Penicillium spp., such as Penicillium expansum or Penicillium purpurogenum; Rhizopus spp., such as Rhizopus stolonifer; Sclerotinia spp., such as Sclerotinias clerotiorum; Verticilium spp., such as Verticilium alboatrum;

[1120] Seed-borne and soil-borne rot and wilt diseases, and seedling diseases caused by pathogens such as Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces euteiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus graminis. sativus) (conidial form: Drechslera, Bipolaris synonym: Helminthosporium); Colletotrichum species, for example, Colletotrichum coccodes; Fusarium species, for example, Fusarium culmorum; Gibberella species, for example, Gibberella zeae; Macrophomina species, for example, Macrophomina phaseolina; Microdochium species, for example, Microdochium nivale; Monographella species, for example, Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, such as Phomopsis sojae; Phytophthora species, such as Phytophthora cactorum; Pyrenophora species, such as Pyrenophora graminea; Pyricularia species, such as Pyricularia oryzae; Pythium species, such as Pythium ultimum;Rhizoctonia species, such as Rhizoctonia solani; Rhizopus species, such as Rhizopus oryzae; Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septorianodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae;

[1121] Cancerous diseases, galls and broom diseases caused by pathogens such as Nectria species, for example Nectria galligena;

[1122] Wilt diseases caused by pathogens such as Verticillium species, for example Verticillium longisporum; Fusarium species, for example Fusarium oxysporum;

[1123] Deformities of leaves, flowers and fruits caused by pathogens such as Exobasidium species, such as Exobasidium vexans; Taphrina species, such as Taphrina deformans;

[1124] Degenerative diseases of woody plants caused by pathogens such as species of the genus Esca, such as Phaemoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; or species of the genus Ganoderma, such as Ganoderma boninense;

[1125] Diseases of plant tubers caused by pathogens such as Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani;

[1126] Diseases caused by bacterial pathogens such as Xanthomonas species, for example Xanthomonas campestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora; Liberibacter species, for example Liberibacter asiaticus; Xyella species, for example Xylella fastidiosa; Ralstonia species, for example Ralstonia solanacearum; Dickea species, for example Dickea solani; Clavibacter species, for example Clavibacter michiganensis; Streptomyces species, for example, Streptomyces scabies.

[1127] Soybean diseases:

[1128] Fungal diseases of leaves, stems, pods and seeds caused by pathogens such as Alternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var.truncatum), brown spot (Septoria glycines), Cercospora leaf spot and blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora (synonym)), Dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), Drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina spp.), trifolii), Phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), sudden death syndrome (Fusarium virguliforme), and target spot (Corynespora cassiicola).

[1129] Fungal diseases of roots and stems caused by pathogens such as black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), Fusarium wilt or wilt, root rot and pod and crown rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmopspora vasinfecta), pod and stem wilt (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum) var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia root rot, stem rot, and damping-off (Rhizoctonia solani), Sclerotinia stem rot (Sclerotinia sclerotiorum), Sclerotinia white rot (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

[1130] Mycotoxins

[1131] In addition, the compounds of formula (I) and the compositions of the present invention can reduce the content of mycotoxins in harvested materials and foods and feeds prepared therefrom. In particular, mycotoxins include, but are not limited to, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2-toxin and HT2-toxin, fumonisin, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids, alkaloids and aflatoxin, which can be produced, for example, by the following fungi: Fusarium species, such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), Fusarium equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudogograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporogony porotrichoides), F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides, etc.; and Aspergillus species, such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, A.versicolor; Penicillium species, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, and P. roqueforti; Claviceps species, such as C. purpurea, C. fusiformis, C. paspali, and C. africana; Stachybotrys species, and others.

[1132] Material protection

[1133] The compounds of the formula (I) and the compositions according to the invention can also be employed in the protection of materials, in particular for protecting industrial materials from attack and destruction by phytopathogenic fungi.

[1134] Furthermore, the compounds of formula (I) and the compositions according to the invention can be used as antifouling compositions alone or in combination with other active ingredients.

[1135] In this article, Indu...

Claims

1. A compound of formula (I), and a salt thereof: in A 1 N or CR 8 ; A 2 O, NR 1 or CR 2A R R2B , in R 1 、R 2A and R 2B For hydrogen, m is 0 or 1, R 3 and R 4 For hydrogen, R 5 For hydrogen, T is hydrogen, L is a methylene group, R 6 for in § 1 is the connection point with L, R 6S1 and R 6S2 are independently hydrogen or R 6S , in R 6S is halogen, C1-C4-alkyl, C2-C6-alkenyl and pyrazolyl, wherein the pyrazolyl is substituted by C1-C4-alkyl, Condition R 6S1 and R 6S2 at least one of which is different from hydrogen, Ring Y forms together with the pyridine ring or pyridazine ring a group of formula (II-a), (II-g), (II-h) or (II-r) in * is the connection point with the group -OQ, # is the connection point with other heterocycles, p is 0 or 1, x 1 is 1 or 2, R 7A For hydrogen, R 7B is hydrogen or C1-C4-alkyl, R 7C For hydrogen, R 7D For hydrogen, R 7E For hydrogen, R 7F For hydrogen, R 7K is hydroxyl group, R 8 For hydrogen, Q is phenyl, Wherein the phenyl group is substituted by one or two substituents Q S replace, in Q S independently selected from halogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C 4- C2-C4-alkynyl and C3-C6-cycloalkyl.

2. The compound of formula (I) and salt thereof according to claim 1, wherein the compound of formula (I) is selected from: 。 3. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound of the formula (I) according to claim 1 and at least one carrier and / or surfactant.

4. A method for controlling harmful microorganisms in crop protection and material protection, characterized in that At least one compound of the formula (I) according to any one of claims 1 to 2 and / or a composition according to claim 3 is applied to the unwanted microorganisms and / or their habitat.

5. Use of one or more compounds of the formula (I) according to any one of claims 1 to 2 and / or a composition according to claim 3 for controlling unwanted microorganisms in crop protection and material protection.

6. A process for preparing a compound of formula (Ia-1), comprising reacting a compound of formula (1) with a compound of formula (2) in process A) to obtain a compound of formula (3), removing the phthalimide group from the compound of formula (3) to obtain a compound of formula (4), and cyclizing the compound of formula (4). and When W is hydrogen, the compound of formula (4) is treated with a dehydrating agent, optionally in the presence of a base, to directly obtain the compound of formula (Ia-1). or When W is an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, the compound of formula (4) is treated with a dehydrating agent in the presence of a base, followed by a deprotection step to obtain a compound of formula (Ia-1), Among them A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q is as defined in any one of claims 1 to 2, and A 2 is O, T is hydrogen, and m is 1; Among them A 1 , Ring Y, p, R 7 and Q are as defined in formula (Ia-1), and U 1 is hydroxy, halogen or C1-C6-alkoxy; Where m, R 3 、R 4 、R 5 , L and R 6 is defined as in formula (Ia-1), and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, Among them, m, A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q are as defined in formula (Ia-1), and W is as defined in formula (2), Among them, m, A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 , Q and W are as defined in formula (3); or By reacting a compound of formula (5) with a compound of formula (2) in method B) to obtain a compound of formula (6a), removing the phthalimide group from the compound of formula (6a) to obtain a compound of formula (6b), and cyclizing the compound of formula (6b), and When W is hydrogen, the compound of formula (6b) can be treated with a dehydrating agent in the presence of a base to directly obtain the compound of formula (7). or When W is an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, optionally in the presence of a base, the compound of formula (6b) is treated with a dehydrating agent, followed by a deprotection step to obtain a compound of formula (7), and the compound of formula (7) is reacted with a compound of formula (8) in the presence of a base and optionally in the presence of a suitable copper salt or complex to obtain a compound of formula (Ia-1), Among them A 1 , ring Y, p and R 7 As defined in formula (Ia-1), X is halogen, preferably bromine, and U 1 is hydroxy, halogen or C1-C6-alkoxy; Where m, R 3 、R 4 、R 5 , L and R 6 As defined in formula (Ia-1), and W is hydrogen or an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, Among them, m, A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 , X and W are as defined above, Among them, m, A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 , X and W are as defined in formula (6a), Among them, m, A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and X is defined as before, wherein Q is as defined above.

7. Compounds of formula (4) in A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q is as defined in any one of claims 1 to 2, m is 1, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.

8. Compounds of formula (7) in A 1 、R 3 、R 4 、R 5 , L, R 6 , ring Y, p and R 7 As defined in any one of claims 1 to 2, m is 1, and X is halogen.

9. Compounds of formula (12): in A 1 、R 3 、R 4 、R 5 , L, R 6 , Ring Y, p, R 7 and Q is as defined in any one of claims 1 to 2, m is 1, E 1 is hydroxy or halogen, E 2 is a hydroxyl group or an amino group, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.

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