Azabicyclyl-substituted heterocycles as novel fungicides

Abstract

The present disclosure provides a compound of formula (I): [Formula 1] TIFF2023529475000106.tif61170(in the formula, A 1 , A 2 , m, R 3 , R 4 , R 5 , L, R 6 , T, ring Y, p, R 7 and Q has the meaning defined herein), compositions containing such compounds, processes and intermediates for their preparation, and their use for controlling plant pathogenic microorganisms, such as plant pathogenic fungi.

Description

[Technical Field]

[0001] The present invention relates to azabicyclyl-substituted heterocyclic compounds and their use for controlling plant pathogenic microorganisms, such as plant pathogenic fungi, as well as processes and intermediates for preparing these compounds. [Background technology]

[0002] Up to now, many crop protection agents have been developed to combat or prevent the spread of microorganisms.However, there is still a need to develop new compounds, in order to provide compounds that are effective against a wide range of plant pathogenic microorganisms such as fungi, have low toxicity, have high selectivity, or can be used at low application rates, and at the same time enable effective pest control.It is also desirable to have new compounds to prevent the emergence of resistance.

[0003] The present invention provides novel compounds for controlling plant pathogenic microorganisms, such as fungi, which have advantages over known compounds and compositions in at least some of their aspects. DETAILED DESCRIPTION OF THE INVENTION

[0004] Compounds of formula (I) The present invention relates to a compound of formula (I):

[0005] [ka]

[0006] (In the formula, A 1 is N or CR 8 and A 2 is O, S, C(=O), S(=O), S(=O)2, NR 1 , or CR 2A R R2B And, R 1 , R 2A , and R 2Bare independently of one another hydrogen, C1-C6-alkyl or C3-C8-cycloalkyl, C-C-alkyl is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkoxycarbonyl, C-C-cycloalkyl, C-C-halocycloalkyl, -O-Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; and C3-C8-Cycloalkyl is halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C 6- optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, C-C-halocycloalkyl, —O—Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; or R 2A and R 2B together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclyl ring, m is 0, 1, or 2; R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, C2-C6-alkenyl, C2-C6-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, C-C-alkyl, C-C-alkoxy, C-C-alkylcarbonyl, C-C-alkoxycarbonyl, C-C-alkenyl, C-C-alkynyl, and -O-Si(C-C-alkyl) are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkoxycarbonyl, C-C-cycloalkyl, C-C-halocycloalkyl, -O-Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; and C3-C8-cycloalkyl, C6-C 14 -Aryl, 5- to 14-membered heteroaryl, and 3- to 14-membered heterocyclyl are selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C 6- optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, C-C-halocycloalkyl, —O—Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; or R 3 and R 4 together with the carbon atoms to which they are attached form a carbonyl, methylidene, C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclyl ring, C3-C8-cycloalkyl rings and 3- to 7-membered heterocyclyl rings are substituted with halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C 6- optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, C-C-halocycloalkyl, —O—Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; R 5is hydrogen, hydroxyl, C-C-alkyl, C-C-alkoxy, C-C-alkylcarbonyloxy, C-C-alkylsulfanyl, C-C-alkylsulfinyl, C-C-alkylsulfonyl, C-C-cycloalkyl, or —O—Si(C-C-alkyl) C-C-alkyl, C-C-alkoxy, C-C-alkylcarbonyloxy, C-C-alkylsulfanyl, C-C-alkylsulfinyl, C-C-alkylsulfonyl, and -O-Si(C-C-alkyl) are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkoxycarbonyl, C-C-cycloalkyl, C-C-halocycloalkyl, -O-Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; and C3-C8-Cycloalkyl is halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C 6- optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, C-C-halocycloalkyl, —O—Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; or 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, T is hydrogen, hydroxyl, C1-C6-alkyl, -C(=O)R 9 , -C(=O)(OR 10 ), -C(=O)N(R 11 )2, -S(=O)R 12 , -S(=O)2R 13 , or -S(=O)2N(R14 )2, R 9 and R 10 are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl, R 11 , R 12 , R 13 , and R 14 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl, L is a direct bond, carbonyl, C1-C6-alkylene, C2-C6-alkenylene, C2-C6-alkynylene, -C(=O)-C1-C6-alkylene-, -C1-C6-alkylene-C(=O)-, -NR L1 -, -NR L2 (C=O)-, -C(=O)NR L3 -, -NR L4 S(=O)2-, -S(=O)2NR L5 -, -C(=NOR L6 )-, -C(=NN(R L7 )2)-, -C(=NR L8 )-, or the expression:

[0007] [ka]

[0008] (In the formula, the C1-C6-alkylene, C2-C6-alkenylene, C2-C6-alkynylene, -C(=O)-C1-C6-alkylene-, and -C1-C6-alkylene-C(=O)- are each independently selected from the group consisting of 1 to 3 substituents L SA optionally substituted with # is the point of attachment to the heterocyclyl moiety; ## is R 6 is the attachment point to L 1 is a direct bond or C1-C6-alkylene, L 2 is a direct bond or C1-C6-alkylene, E is C3-C8-cycloalkyl, C3-C8-cycloalkenyl, or 3- to 7-membered heterocyclyl, The C3-C8-cycloalkyl, C3-C8-cycloalkenyl, and 3- to 7-membered heterocyclyl may be sequentially selected from 1 to 3 substituents L SC optionally substituted with R L1 , R L2 , R L3 , and R L4 are independently hydrogen or C1-C6-alkyl, R L5 , R L6 , R L7 , and R L8 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl, L SA are independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, C-C-halocycloalkyl, C-C-alkoxycarbonyl, -O-Si(C-C-alkyl) or 3- to 7-membered heterocyclyl, and / or Two substituents L attached 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, L SC are independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, 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, and / or 2 L SCthe substituents, together with the carbon atoms to which they are attached, form a C3-C8-cycloalkyl ring, R 6 is C3-C 12 -Carbocyclyl, 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 -Carbocyclylsulfinyl, C6-C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclylsulfinyl, C3-C 12 -Carbocyclylsulfonyl, C6-C 14 -arylsulfonyl, 5- to 14-membered heteroarylsulfonyl, 3- to 14-membered heterocyclylsulfonyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkylsulfanyl, C-C-alkylsulfinyl, or C-C-alkylsulfonyl, C1-C3-Alkoxy, C1-C3-haloalkoxy, C1-C3-alkylsulfanyl, C1-C3-alkylsulfinyl and C1-C3-alkylsulfonyl are C3-C 12 -Carbocyclyl, C6-C 14 -substituted with one substituent selected from the group consisting of aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl; Said C3-C 12 -Carbocyclyl, C6-C 14 -aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl are each, in order, 1 to 4 R 6S optionally substituted with a substituent; C3-C 12 -Carbocyclyl, C6-C14 -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 -Carbocyclylsulfinyl, C6-C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclylsulfinyl, C3-C 12 -Carbocyclylsulfonyl, C6-C 14 -arylsulfonyl, 5- to 14-membered heteroarylsulfonyl, and 3- to 14-membered heterocyclylsulfonyl are each a group selected from 1 to 4 R 6S optionally substituted with a substituent; R 6S is halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-halo-alkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C2-C6-alkylnyloxy, C2-C6- Haloalkylnyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkyl-sulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C8-cycloalkenyl, C6-C 14-aryl, 5- or 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, 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-Alkynnyloxy, C2-C6-Haloalkylnyloxy, C1-C6-Alkylsulfanyl, C1-C6-Haloalkylsulfanyl, C1-C6-Alkylsulfinyl, C1-C6-Haloalkylsulf -phenyl, C-C-alkylsulfonyl, C-C-haloalkylsulfonyl, -O-Si(C-C-alkyl) and -Si(C-C-alkyl) are further optionally substituted by 1 to 3 substituents independently selected from the group consisting of cyano, hydroxyl, C-C-alkoxy, C-C-haloalkoxy, -O-Si(C-C-alkyl) -, -Si(C-C-alkyl) -, C-C-cycloalkyl, C-C-halocycloalkyl and 3- to 7-membered heterocyclyl; or two C1-C6-alkyl substituents attached to the same carbon atom together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl ring, and C3-C8-Cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, C3-C8-cycloalkenyl, C6-C 14-Aryl, 5- or 6-membered heteroaryl, and 3- to 7-membered heterocyclyl are selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkoxycarbonyl, C-C-haloalkoxycarbonyl, C-C 6- optionally further substituted with 1 to 4 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, and C-C-halocycloalkyl; and R 15 are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl is in turn optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl; and The C3-C8-cycloalkyl may also be halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C 6- optionally substituted with 1 to 4 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, and C-C-halocycloalkyl; R 16 , R 17 , R 18 , and R 19 are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl, wherein said C1-C6-alkyl and C1-C6-haloalkyl are in turn optionally substituted by 1 to 3 substituents independently selected from the group consisting of cyano, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl; the ring Y together with the pyridine ring or pyridazine ring forms a bicyclic heterocyclyl or bicyclic heteroaryl, respectively; p is 0, 1, 2, 3, or 4; R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, 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, C 1-C6-Alkylsulfanyl, C1-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-cycloalkyl, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, C3-C8-cycloalkyloxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -N(R 20 )2, -C(=NR 21 )R 22 , -NR 23 C(=O)R 24, -C(=O)(OR 25 ), -C(=O)N(R 26 )2, -S(=O)2N(R 27 )2, or -S(=O)(=NR 28 )R 29 And, 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 each independently selected from 1 to 3 R 7Sa optionally substituted with a substituent; 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 each independently selected from 1 to 3 R 7Sc optionally substituted with a substituent; and R 20 are independently hydrogen, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, C-C-alkenyl, C-C-haloalkenyl, C-C-alkynyl, C-C-haloalkynyl, C-C-cycloalkyl, C-C-halocycloalkyl, or 3- to 7-membered heterocyclyl, C1-C6-Alkyl, C1-C6-Haloalkyl, C1-C6-Alkoxy, C2-C6-Alkenyl, C2-C6-Haloalkenyl, C2-C6-Alkynyl and C2-C6-Haloalkynyl may in turn be one to three substituents R 7Sa optionally substituted with and C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl are each, in order, one to three substituents R 7Sc optionally substituted with R 21 and R 22 are independently hydroxyl, amino, cyano, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, mono-(C-C-alkyl)amino, or di-(C-C-alkyl)amino, C1-C6-Alkyl, C1-C6-Haloalkyl, C1-C6-alkoxy, mono-(C1-C6-alkyl)amino, and di-(C1-C6-alkyl)amino are each, in order, one to three R 7Sa optionally substituted with a substituent; R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , and R 29 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, and C3-C8-cycloalkyl, C1-C6-Alkyl and C1-C6-Haloalkyl are each represented by 1 to 3 R 7Sa optionally substituted with a substituent; and Similarly, C3-C8-cycloalkyl has 1 to 3 R 7Sc optionally substituted with a substituent; R 7Saare independently cyano, hydroxyl, carboxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, C-C-halocycloalkyl, C-C-alkoxycarbonyl, -O-Si(C-C-alkyl)3, -Si(C-C-alkyl)3, or 3- to 7-membered heterocyclyl, R 7Sc are independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, 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, or Two Rs 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, R 8 is hydrogen or halogen, Q is C6-C 14 -Aryl, C3-C 12 -carbocyclyl, 3- to 14-membered heterocyclyl, or 5- to 14-membered heteroaryl; C6-C 14 -Aryl, C3-C 12 -carbocyclyl, 3- to 14-membered heterocyclyl, or 5- to 14-membered heteroaryl is substituted with 1 to 5 substituents Q S optionally substituted with Q S is halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-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, -Si(C1-C6-alkyl)3, -OC(=O)R 30 , -NR 31 C(=O)R 32 , -C(=O)N(R 33 )2, C(=S)R 34 , -C(=S)N(R 35 )2, -C(=NR 36 )R 37 , -C(=NOR 38 )R 39 , and -N(R 40 )2 independently selected from the group consisting of: 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, -O-Si(C1-C6-alkyl)3, and -Si( C-C-alkyl)3 is in turn optionally substituted by 1 to 3 substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkoxycarbonyl, C-C-haloalkoxycarbonyl, C-C-cycloalkyl, C-C-halocycloalkyl, -Si(C-C-alkyl)3, and 3- to 7-membered heterocyclyl, and The C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, and 5- to 14-membered heteroaryl are, in this order, halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, 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- optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, and 3- to 7-membered heterocyclyl; said C3-C8-cycloalkyl, C3-C8-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; and R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37, R 38 , and R 39 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, or C1-C6-alkoxy, wherein said C-C-alkyl, C-C-haloalkyl, and C-C-alkoxy are in turn optionally substituted by 1 to 3 substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkoxycarbonyl, C-C-haloalkoxycarbonyl, C-C-cycloalkyl, C-C-halocycloalkyl, -Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; and R 40 is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C 6- Alkenyl, C2-C 6- haloalkenyl, or C3-C8-cycloalkyl, The C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C 6- alkenyl, and C2-C6-haloalkenyl, in turn, are optionally substituted by 1 to 3 substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C3-C8-cycloalkyl, C3-C8-halocycloalkyl, -Si(C1-C6-alkyl)3, and 3- to 7-membered heterocyclyl, and The C3-C8-cycloalkyl may also be halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, 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-optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, and 3- to 7-membered heterocyclyl; said C3-C8-cycloalkyl, C3-C8-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; or Two Qs bonded to the same carbon atom S the substituents, together with the carbon atoms to which they are attached, form a C3-C8-cycloalkyl ring, and their N-oxides, salts, and hydrates, as well as hydrates of said salts and N-oxides.

[0009] The present invention further relates to compositions comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable adjuvant.

[0010] 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.

[0011] The present invention further relates to a method for controlling plant pathogenic fungi, comprising the step of applying to plants, plant parts, seeds, fruits or the soil in which the plants in need of treatment are growing at least one compound of formula (I) as defined herein or a composition as defined herein.

[0012] The present invention also relates to processes and intermediates for preparing compounds of formula (I).

[0013] Unless otherwise stated, the following definitions apply to substituents and radicals used throughout the specification and claims. As used herein, the term "halogen" refers to a fluorine, chlorine, bromine, or iodine atom.

[0014] The term "methylidene," as used herein, refers to a CH2 group attached to a carbon atom through a double bond.

[0015] The term "halomethylidene," as used herein, refers to a CX2 group attached to a carbon atom through a double bond, where X is a halogen.

[0016] The term "oxo," as used herein, refers to an oxygen atom attached to a carbon or sulfur atom through a double bond.

[0017] The term "formyl" as used herein refers to -CH(=O).

[0018] The term "C1-C6-alkyl" as used herein refers to a saturated, branched, or straight 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 (iso-propyl), butyl (n-butyl), 1-methylpropyl (sec-butyl), 2-methylpropyl (iso-butyl), 1,1-dimethylethyl (tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl. In particular, the hydrocarbon chain has 1, 2, 3 or 4 carbon atoms ("C1-C4-alkyl"), for example methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl or tert-butyl.

[0019] The term "C1-C6-haloalkyl" as used herein refers to a (C1-C6-alkyl) group, as defined above, in which one or more hydrogen atoms are replaced with one or more halogen atoms, which may be the same or different.Examples of C1-C6-haloalkyl include but are not limited to chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, and 1,1,1-trifluoroprop-2-yl.

[0020] The term "C1-C6-fluoroalkyl" as used herein refers to a C1-C6-alkyl group, as defined above, in which one or more hydrogen atoms are replaced with one or more fluorine atoms, which may be the same or different. Examples of C1-C6-fluoroalkyl include, but are not limited to, monofluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, and 2,2,2-trifluoroethyl.

[0021] The term "C-C alkylene" as used herein refers to a divalent C-C alkyl group as defined herein. Examples of C-C alkylene 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.

[0022] As used herein, the terms "C3-C8-cycloalkyl" and "C3-C8-cycloalkyl ring" refer to a saturated monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms. Examples of C3-C8-cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. In particular, the cycloalkyl has 3 to 6 carbon atoms.

[0023] The term "C3-C8-halocycloalkyl" as used herein refers to a saturated hydrocarbon ring system in which all ring members, ranging from 3 to 8, are carbon atoms and one or more hydrogen atoms are replaced by one or more halogen atoms, which may be the same or different.

[0024] The term "C2-C6-alkenyl" as used herein refers to an unsaturated branched or linear hydrocarbon chain having 2, 3, 4, 5, or 6 carbon atoms and containing at least one double bond. Examples of C2-C6-alkenyl include 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 aryl). or "isopropenyl") group, 2-methylprop-2-enyl group, 1-methylprop-2-enyl group, 2-methylprop-1-enyl group, 1-methylprop-1-enyl group, 3-methylbut-3-enyl group, 2-methylbut-3-enyl group, 1-methylbut-3-enyl group, 3-methylbut-2-enyl group, 2-methylbut-2-enyl group, 1-methylbut-2-enyl group, 3-methylbut-1-enyl group, 2-methylbut-1-enyl group, 1-methylbut-1-enyl group, 1,1-dimethylprop-2-enyl group, 1-ethylprop-1-enyl group, 1-propylvinyl group, 1-isopropylvinyl group, 4-methylpent-4-enyl group, 3-methylpent-4-enyl group, 2-methylpent-4-enyl group, 1-methylpent-4-enyl group, 4-methylpent-3-enyl group, 3-methylpent-3-enyl group, 2-methylpent-3-enyl group, 1-methylpent but-3-enyl group, 4-methylpent-2-enyl group, 3-methylpent-2-enyl group, 2-methylpent-2-enyl group, 1-methylpent-2-enyl group, 4-methylpent-1-enyl group, 3-methylpent-1-enyl group, 2-methylpent-1-enyl group, 1-methylpent-1-enyl group, 3-ethylbut-3-enyl group, 2-ethylbut-3-enyl group, 1-ethylbut-3-enyl group enyl group, 3-ethylbut-2-enyl group, 2-ethylbut-2-enyl group, 1-ethylbut-2-enyl group, 3-ethylbut-1-enyl group, 2-ethylbut-1-enyl group, 1-ethylbut-1-enyl group, 2-propylprop-2-enyl group, 1-propylprop-2-enyl group, 2-isopropylprop-2-enyl group, 1-isopropylprop-2-enyl group, 2-propylprop Examples of the alkyl group include, but are not limited to, 1-propylprop-1-enyl, 2-isopropylprop-1-enyl, 1-isopropylprop-1-enyl, 3,3-dimethylprop-1-enyl, 1-(1,1-dimethylethyl)ethenyl, buta-1,3-dienyl, penta-1,4-dienyl, hexa-1,5-dienyl, or methylhexadienyl.

[0025] The term "C2-C6-alkynyl" as used herein 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 ethynyl, prop-1-ynyl, prop-2-ynyl hydrocarbon chain (or "propargyl"), but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 1-methylprop-2-ynyl, 2-methylbut-3-ynyl, 1-methylbut-3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl, 1-ethylprop-2-ynyl, 3-methylpent-4-ynyl, 2-methylpent-4-ynyl, 2-methylpent-5-ynyl, 2-methylpent-6-ynyl, 2-methylpent-7-ynyl, 2-methylpent-8-ynyl, 2-methylpent-9-ynyl, 2-methylpent-10-ynyl, 2-methylpent-11-ynyl, 2-methylpent-12-ynyl, 2-methylpent-13-ynyl, 2-methylpent-14-ynyl, 2-methylpent-15-ynyl, 2-methylpent-16-ynyl, 2-methylpent-17-ynyl, 2-methylpent-18-ynyl, 2-methylpent-19 ... Examples of methylpent-4-ynyl groups include, but are not limited to, 1-methylpent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl, 4-methylpent-2-ynyl, 1-methylpent-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.

[0026] The term "C2-C6-haloalkenyl" as used herein refers to a C2-C6-alkenyl group, as defined above, in which one or more hydrogen atoms have been replaced by one or more halogen atoms, which may be the same or different.

[0027] The term "C2-C6-haloalkynyl" as used herein refers to a C2-C6-alkynyl group, as defined above, in which two or more hydrogen atoms have been replaced by one or more halogen atoms, which may be the same or different.

[0028] The term "C1-C6-alkoxy" as used herein refers to a group of the formula (C1-C6-alkyl)-O-, in which the term "C1-C6-alkyl" is defined herein. Examples of C1-C6-alkoxy include 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, Examples of alkoxy include, but are not limited to, 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 also applies to alkoxy, such as alkoxyalkyl, alkoxyalkoxy, as part of a compound substituent, unless otherwise defined.

[0029] The term "C-C-haloalkoxy" as used herein refers to a C-C-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 C-C-haloalkoxy include, but are not limited to, chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, and 1,1,1-trifluoroprop-2-oxy.

[0030] The term "C1-C6-hydroxyalkyl" as used herein refers to a C1-C6-alkyl group as defined above, in which at least one hydrogen atom is replaced with a hydroxyl group. Examples of C1-C6-hydroxyalkyl include, but are not limited to, hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 1-hydroxypropyl, 1-hydroxypropan-2-yl, 2-hydroxypropan-2-yl, 2,3-dihydroxypropyl, and 1,3-dihydroxypropan-2-yl.

[0031] The term "C3-C8-cycloalkoxy" as used herein refers to a monocyclic saturated cycloalkoxy radical having 3 to 8 and preferably 3 to 6 carbon ring members, such as (but not limited to) cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy. This also applies to cycloalkoxy as part of a compound substituent, such as cycloalkoxyalkyl, unless otherwise defined.

[0032] The term "C3-C8-halocycloalkoxy" as used herein refers to a C3-C8-cycloalkoxy group, as defined above, in which one or more hydrogen atoms have been replaced by one or more halogen atoms, which may be the same or different.

[0033] The term "C2-C6-alkenyloxy" as used herein refers to the formula (C2-C6-alkenyl)-O-, where the term "C1-C6-alkenyl" group is as defined herein. Examples of C2-C6-alkenyl include ethenyloxy (or "vinyloxy"), prop-2-en-1-yloxy (or "allyl"), prop-1-en-1-yloxy, but-3-enyloxy, but-2-enyloxy, but-1-enyloxy, pent-4-enyloxy, pent-3-enyloxy, pent-2-enyloxy, pent-1-enyloxy, hex-5-enyloxy, hex-4-enyloxy, hex-3-enyloxy, hex-2-enyloxy, hex-1-enyloxy, prop-1-en-2-yl Oxy (or "isopropenyloxy"), 2-methylprop-2-enyloxy, 1-methylprop-2-enyloxy, 2-methylprop-1-enyloxy, 1-methylprop-1-enyloxy, 3-methylbut-3-enyloxy, 2-methylbut-3-enyloxy, 1-methylbut-3-enyloxy, 3-methylbut-2-enyloxy, 2-methylbut-2-enyloxy, 1-methylbut-2-enyloxy, 3-methylbut-1-enyloxy, 2-methylbut-1-enyloxy, 1-methylbut-1-enyloxy, 1,1-Dimethylprop-2-enyloxy, 1-ethylprop-1-enyloxy, 1-propylvinyloxy, 1-isopropylvinyloxy, 4-methylpent-4-enyloxy, 3-methylpent-4-enyloxy, 2-methylpent-4-enyloxy, 1-methylpent-4-enyloxy, 4-methylpent-3-enyloxy, 3-methylpent-3-enyloxy, 2-methylpent-3-enyloxy, 1-methylpent but-3-enyloxy, 4-methylpent-2-enyloxy, 3-methylpent-2-enyloxy, 2-methylpent-2-enyloxy, 1-methylpent-2-enyloxy, 4-methylpent-1-enyloxy, 3-methylpent-1-enyloxy, 2-methylpent-1-enyloxy, 1-methylpent-1-enyloxy, 3-ethylbut-3-enyloxy, 2-ethylbut-3-enyloxy, 1-ethylbut-3 -enyloxy, 3-ethylbut-2-enyloxy, 2-ethylbut-2-enyloxy, 1-ethylbut-2-enyloxy, 3-ethylbut-1-enyloxy, 2-ethylbut-1-enyloxy, 1-ethylbut-1-enyloxy, 2-propylprop-2-enyloxy, 1-propylprop-2-enyloxy, 2-isopropylprop-2-enyloxy, 1-isopropylprop-2-enyloxy, 2-propylprop Examples of the alkoxy group include, but are not limited to, 1-prop-1-enyloxy, 1-propylprop-1-enyloxy, 2-isopropylprop-1-enyloxy, 1-isopropylprop-1-enyloxy, 3,3-dimethylprop-1-enyloxy, 1-(1,1-dimethylethyl)ethenyloxy, buta-1,3-dienyloxy, penta-1,4-dienyloxy, hexa-1,5-dienyloxy, or methylhexadienyloxy groups.

[0034] The term "C2-C6-haloalkenyloxy" as used herein refers to a (C2-C6-alkenyl)-O- group, as defined above, in which one or more hydrogen atoms have been replaced by one or more halogen atoms, which may be the same or different.

[0035] The term "C2-C6-alkenylene" as used herein refers to a divalent C2-C6-alkenyl group, as defined herein. Examples of C2-C6-alkenylene include, but are not limited to, ethenylene, 1,3-propenylene, butenylene, pentenylene, hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecenylene, and the like.

[0036] The term "C2-C6-haloalkynyloxy" as used herein refers to a (C2-C6-alkynyl)-O- group in which two or more hydrogen atoms have been replaced by one or more halogen atoms, which may be the same or different, as defined above.

[0037] The term "C-C-alkylsulfanyl," as used herein, refers to a saturated, linear or branched group of the formula (C-C-alkyl)-S-, where the term "C-C-alkyl" is defined herein. Examples of C-C-alkylsulfanyl include, but are not limited to, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, sec-butylsulfanyl, isobutylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, and hexylsulfanyl groups.

[0038] The term "C1-C6-haloalkylsulfanyl" as used herein refers to C1-C6-alkylsulfanyl, 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.

[0039] The term "C3-C8-cycloalkylsulfanyl" as used herein refers to a saturated monovalent monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms and attached 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.

[0040] The term "C1-C6-alkylsulfinyl," as used herein, refers to a saturated, linear or branched group of the formula (C1-C6-alkyl)-S(=O)-, where the term "C1-C6-alkyl" is defined herein. Examples of C1-C6-alkylsulfinyl include saturated, linear or branched alkylsulfinyl radicals having 1 to 8, preferably 1 to 6, and more preferably 1 to 4 carbon atoms, such as (but not limited to), methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexyl C1-C6-alkylsulfinyl such as sulfinyl, 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.

[0041] The term "C1-C6-haloalkylsulfinyl" as used herein refers to a C1-C6-alkylsulfinyl, 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.

[0042] The term "C3-C8-cycloalkylsulfinyl" as used herein refers to a saturated monovalent monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms and attached to the backbone via an -S(=O)- group. Examples of monocyclic C3-C8-cycloalkylsulfinyl include, but are not limited to, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, cycloheptylsulfinyl, or cyclooctylsulfinyl.

[0043] The term "C1-C6-alkylsulfonyl" as used herein refers to a saturated, linear or branched group of formula (C1-C6-alkyl)-S(=O)2-, where the term "C1-C6-alkyl" is defined herein. Examples of C1-C6-alkylsulfonyl include 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-methylpentyl ...,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1,1-dimethylethylsulf and 1-ethyl-2-methylpropylsulfonyl.

[0044] The term "C1-C6-haloalkylsulfonyl" as used herein refers to C1-C6-alkylsulfonyl, 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.

[0045] The term "C3-C8-cycloalkylsulfonyl" as used herein refers to a saturated monovalent monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms and attached to the backbone via an -S(=O)2- group. Examples of monocyclic C3-C8-cycloalkylsulfonyl include, but are not limited to, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cycloheptylsulfonyl, or cyclooctylsulfonyl.

[0046] The term "C1-C6-alkylcarbonyl" as used herein refers to a saturated linear or branched group of the formula (C1-C6-alkyl)-C(=O)-, wherein the term "C1-C6-alkyl" is defined herein.

[0047] The term "C1-C6-haloalkylcarbonyl" as used herein refers to a C1-C6-alkylcarbonyl, 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.

[0048] The term "C1-C6-alkylcarbonyloxy" as used herein refers to a saturated linear or branched group of the formula (C1-C6-alkyl)-C(=O)-, wherein the term "C1-C6-alkyl" is defined herein.

[0049] The term "C1-C6-alkoxycarbonyl" as used herein refers to a saturated linear or branched group of the formula (C1-C6-alkoxy)-C(=O)-, wherein the term "C1-C6-alkoxy" is defined herein.

[0050] The term "C1-C6-haloalkoxycarbonyl" as used herein refers to a C1-C6-alkoxycarbonyl, 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.

[0051] The term "mono-(C-C alkyl)amino" as used herein refers to an amino radical having one C-C alkyl group, as defined herein. Examples of mono-(C-C alkyl)amino include, but are not limited to, N-methylamino, N-ethylamino, N-isopropylamino, Nn-propylamino, N-isopropylamino, and N-tert-butylamino.

[0052] The term "di-(C-C)-alkylamino" as used herein refers to an amino radical having two independently selected C-C alkyl groups, as defined herein. Examples of C-C-dialkylamino include, but are not limited to, N,N-dimethylamino, N,N-diethylamino, N,N-diisopropylamino, N-ethyl-N-methylamino, N-methyl-Nn-propylamino, N-isopropyl-Nn-propylamino, and N-tert-butyl-N-methylamino.

[0053] As used herein, "C3-C 12 The term "-carbocyclyl" refers to a saturated or partially unsaturated hydrocarbon ring system in which all ring members, varying from 3 to 12, are carbon atoms. The ring system may be monocyclic or polycyclic (fused, spiro, or bridged). C3-C 12 -Carbocyclyl has C3-C 12 -cycloalkyl (monocyclic or bicyclic), C3-C 12-cycloalkenyl (monocyclic or bicyclic), bicyclic systems containing an aryl (e.g., phenyl) fused to a monocyclic C3-C8-cycloalkyl (e.g., tetrahydronaphthalenyl, indanyl, 3-bicyclo[4.2.0]octa-1,3,5-trienyl), bicyclic systems containing an aryl (e.g., phenyl) fused to a monocyclic C3-C8-cycloalkenyl (e.g., indenyl, dihydronaphthalenyl), and tricyclic systems containing a cyclopropyl bonded via one carbon atom to a bicyclic system containing an aryl (e.g., phenyl) fused to a C3-C8-cycloalkyl or C3-C8-cycloalkenyl. 12 The -carbocyclyl can be attached to the parent molecular moiety through any carbon atom.

[0054] As used herein, "C3-C 12 The term "cycloalkenyl" refers to an unsaturated, monovalent, monocyclic, or bicyclic hydrocarbon ring containing 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms and one or two double bonds. Examples of monocyclic C3-C8-cycloalkenyl groups include, but are not limited to, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, and cyclooctenyl groups. Bicyclic C6-C 12 Examples of -cycloalkenyl groups include, but are not limited to, 3-bicyclo[4.2.0]octa-1,3,5-trienyl, bicyclo[2.2.1]hept-2-enyl, or bicyclo[2.2.2]oct-2-enyl.

[0055] As used herein, "C6-C 14 The term "aryl" refers to an aromatic hydrocarbon ring system in which all of the ring members, ranging from 6 to 14, preferably 6 to 10, are carbon atoms. The ring system may be monocyclic or fused polycyclic (e.g., bicyclic or tricyclic). Examples of aryl include, but are not limited to, phenyl, azulenyl, and naphthyl.

[0056] The term "3- to 14-membered heterocyclyl," as used herein, refers to a saturated or partially unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13-, or 14-membered ring system containing one to four heteroatoms independently selected from the group consisting of oxygen, nitrogen, and sulfur. If the ring system contains two or more oxygen atoms, they are not immediately adjacent. Heterocycles include, but are not limited to, 3- to 7-membered monocyclic heterocycles and 8- to 14-membered polycyclic (e.g., bicyclic or tricyclic) heterocycles. The 3- to 14-membered heterocycle can be attached to the parent molecular moiety through any carbon or nitrogen atom contained within the heterocycle. Examples of saturated heterocycles include three-membered rings such as oxiranyl and aziridinyl, four-membered rings such as azetidinyl, oxetanyl, and thietanyl, five-membered rings such as tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, and thiadiazolidinyl, piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, and the like. Examples of unsaturated heterocycles include, but are not limited to, 6-membered rings such as dihydrofuranyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothiopyranyl, dithianyl, morpholinyl, 1,2-oxazinanyl, oxathianyl, and thiomorpholinyl, or 7-membered rings such as oxepanyl, azepanyl, 1,4-diazepanyl, and 1,4-oxazepanyl. Examples of unsaturated heterocycles include, but are not limited to, 5-membered rings such as dihydrofuranyl, 1,3-dioxolyl, dihydrothienyl, pyrrolinyl, dihydroimidazolyl, dihydropyrazolyl, isoxazolinyl, dihydrooxazolyl, and dihydrothiazolyl, or 6-membered rings such as pyranyl, thiopyranyl, thiazinyl, and thiadiazinyl.As defined herein, a bicyclic heterocycle may consist of a monocyclic C3-C8-cycloalkyl, a monocyclic C3-C8-cycloalkenyl, or a monocyclic heteroaryl fused to a monocyclic heterocycle, or a monocyclic heterocycle fused to an aryl (e.g., phenyl), a C3-C8-cycloalkyl, a C3-C8-cycloalkenyl, or a monocyclic heterocycle. When two monocyclic heterocycles or one monocyclic heterocycle and one monocyclic heteroaryl containing a nitrogen atom are fused, the nitrogen atom may be in a bridgehead position (e.g., 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). A tricyclic heterocycle may consist of a monocyclic cycloalkyl attached via one common atom to a bicyclic heterocycle.

[0057] As used herein, the terms "3- to 7-membered heterocyclyl" and "3- to 7-membered heterocyclyl ring" refer to a saturated 3-, 4-, 5-, 6-, or 7-membered ring system containing one, one, or three heteroatoms independently selected from the group consisting of oxygen, nitrogen, and sulfur. Examples include oxiranyl, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, and the like. Preferred 3- to 7-membered heterocyclyls include, but are not limited to, oxiranyl, aziridinyl, azetidinyl, oxetanyl, tetrahydrofuranyl, 1,3-dioxolanyl, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxanyl, morpholinyl, 1,2-oxazinanyl, oxathianyl, thiomorpholinyl, oxepanyl, azetidinyl, 1,4-diazepanyl, and 1,4-oxazepanyl.

[0058] The term "5- to 14-membered heteroaryl" as used herein refers to an aromatic ring system containing 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen, and sulfur. If the ring system contains more than one oxygen atom, they are not immediately 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 heteroaryls can be attached to the parent molecular moiety through any carbon or nitrogen atom contained within the heterocycle.

[0059] As used herein, the term "5- or 6-membered heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring system containing 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen, and sulfur. Examples of 5-membered monocyclic heteroaryls include, but are not limited to, furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, isoxazolyl, oxazolyl, oxadiazolyl, oxatriazolyl, isothiazolyl, thiazolyl, thiadiazolyl, and thiatriazolyl. Examples of 6-membered monocyclic heteroaryls include, but are not limited to, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, and tetrazinyl.

[0060] The term "7- to 14-membered heteroaryl," as used herein, refers to a 7-, 8-, 9-, 10-, 11-, 12-, 13-, or 14-membered aromatic polycyclic (e.g., bicyclic or tricyclic) ring system containing one, two, or three heteroatoms independently selected from the group consisting of oxygen, nitrogen, and sulfur. As defined herein, a bicyclic heteroaryl may consist of a monocyclic heteroaryl fused to an aryl (e.g., phenyl) or monocyclic heteroaryl. Examples of bicyclic heteroaryls include, but are not limited to, 9-membered rings such as indolyl, indolizinyl, isoindolyl, benzimidazolyl, imidazopyridinyl, indazolyl, benzotriazolyl, purinyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, and benzisoxazolyl, or 10-membered rings such as quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, pteridinal, and benzodioxinyl. In 9- or 10-membered bicyclic heteroaryls, including two fused 5- or 6-membered monocyclic heteroaryls, the nitrogen atom may be in a bridgehead position (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 heterocycles include, but are not limited to, carbazolyl, acridinyl, and phenazinyl.

[0061] As used herein, "C3-C 12 -carbocyclyloxy, C3-C8-cycloalkoxy, C6-C 14 The terms "5-membered to 14-membered heteroaryloxy," "5-membered to 14-membered heteroaryloxy," and "3-membered to 14-membered heterocyclyloxy" refer to groups in which R is C3-C6, as defined herein. 12 -Carbocyclyl, C3-C8-cycloalkyl, C6-C 14 -Specifies a group of formula -OR which is an aryl, 5- to 14-membered heteroaryl, or 3- to 14-membered heterocyclyl group.

[0062] As used herein, "C3-C 12 -carbocyclylsulfanyl", "C6-C 14 "5-membered to 14-membered heteroarylsulfanyl," "5-membered to 14-membered heteroarylsulfanyl," and "3-membered to 14-membered heterocyclylsulfanyl" refer to groups of the formula -SR, where R is each C-C 12 -Carbocyclyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 14-membered heterocyclyl group).

[0063] As used herein, "C3-C 12 -carbocyclylsulfinyl", "C6-C 14 "5- to 14-membered heteroarylsulfinyl," "5- to 14-membered heteroarylsulfinyl," and "3- to 14-membered heterocyclylsulfinyl" refer to groups of the formula -(S=O)-R, where R is each C-C, as defined herein. 12 -Carbocyclyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 14-membered heterocyclyl group).

[0064] As used herein, "C3-C 12 -carbocyclylsulfonyl", "C6-C 14 "5- to 14-membered heteroarylsulfonyl," "5- to 14-membered heteroarylsulfonyl," and "3- to 14-membered heterocyclylsulfonyl" refer to groups of the formula -(S=O)2-R, where R is each C3-C 12 -Carbocyclyl, C6-C 14 -aryl, 5- to 14-membered heteroaryl, or 3- to 14-membered heterocyclyl group).

[0065] The term "leaving group," as used herein, should be understood to mean a group that is displaced from a compound in a substitution or elimination reaction, e.g., a halogen atom, a trifluoromethanesulfonate ("triflate") group, an alkoxy, a methanesulfonate, or a p-toluenesulfonate.

[0066] The phrase "as described herein" refers to the variables m, p, Q, A 1 , A 2 , T, R 1 , R 2A , R 2B , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , Y, and L, the broad definitions of the variables, as well as preferred, more preferred, and even more preferred, if any, are incorporated by reference.

[0067] Compounds resulting from combinations that violate the laws of nature and would therefore be excluded by a person skilled in the art based on their specialized knowledge are not encompassed herein, for example, ring structures having three or more adjacent oxygen atoms are excluded.

[0068] Compounds of formula (I) may suitably be in their free form, in the form of a salt, an N-oxide or in the form of a solvate (eg a hydrate).

[0069] Depending on the nature of the substituents, the compound of formula (I) can exist in different stereoisomeric forms.These stereoisomers are, for example, enantiomers, diastereomers, atropisomers, or geometric isomers.Therefore, the present invention encompasses both pure stereoisomers and any mixtures of these isomers.If a compound can exist in equilibrium in two or more tautomeric forms, a reference to a compound by describing one tautomer is considered to include all tautomeric forms.

[0070] Any compound of the present invention may also exist in one or more geometric isomeric forms depending on the number of double bonds in the compound. Geometric isomers due to the nature of the substituents on the double bond or ring may exist in cis (=Z-) or trans (=E-) form. Therefore, the present invention equally relates to all geometric isomers and all possible mixtures in any ratio.

[0071] Depending on the nature of the substituents, the compounds of formula (I) may exist in the form of the free compounds and / or their salts, such as pesticidal active salts.

[0072] Pesticide active salts include acid addition salts of inorganic and organic acids and salts of conventional bases. Examples of inorganic acids include hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide, sulfuric acid, phosphoric acid, nitric acid, and acid salts such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, alkanoic acids (carbonic acid, acetic acid, trifluoroacetic acid, trichloroacetic acid, and propionic acid), as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or di-unsaturated fatty acids having 6 to 20 carbon atoms, alkyl sulfate monoesters, alkyl sulfonic acids (sulfonic acids having linear or branched alkyl groups having 1 to 20 carbon atoms), aryl sulfonic acids or aryl disulfonic acids (phenyl sulfonates having one or two sulfonic acid groups). and naphthyl), alkylphosphonic acids (phosphonic acids with linear or branched alkyl radicals having 1 to 20 carbon atoms), and arylphosphonic or aryldiphosphonic acids (aromatic radicals such as phenyl and naphthyl with one or two phosphonic acid radicals) (the alkyl and aryl groups may have further substituents, e.g., p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.).

[0073] Solvates of the compounds of the invention or their salts are stoichiometric compositions of the compound and a solvent.

[0074] The compounds of the present invention may exist in multiple crystalline and / or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates, and hydrates.

[0075] Preferably, the present invention provides a compound of formula (I) A 1 is N or CR 8and A 2 is O, S, C(=O), S(=O), S(=O)2, NR 1 , or CR 2A R R2B And, R 1 , R 2A , and R 2B are independently of one another hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl, C1-C4-Alkyl is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, 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, and C3-C6-Cycloalkyl is halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C 6- optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, C-C-halocycloalkyl, —O—Si(C-C-alkyl) and 3- to 7-membered heterocyclyl; m is 0, 1, or 2; R 3 and R 4 are independently hydrogen, fluoro, chloro, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C3-C6-cycloalkyl, C1-C4-Alkyl, C2-C4-Alkenyl, and C2-C4-Alkynyl are optionally substituted by 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl; and C3-C6-Cycloalkyl is fluoro, chloro, hydroxyl, oxo, methylidene, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, and C-C-halocycloalkyl; R 5 is hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylsulfanyl, C-C-alkyl, C-C-alkoxy, and C-C-alkylsulfanyl are optionally substituted by 1 to 3 substituents independently selected from the group consisting of fluoro, chlorohydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, and C-C-halocycloalkyl; and C3-C6-Cycloalkyl is fluoro, chloro, hydroxyl, oxo, methylidene, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C-C-cycloalkyl, and C-C-halocycloalkyl; or R 3 and R 5 or R 4 and R 5 together with the carbon atoms to which they are attached form a C3-C6-cycloalkyl ring, T is hydrogen or C1-C4-alkyl, L is a direct bond, C1-C6-alkylene, or a group of the formula:

[0076] [ka]

[0077] wherein the C1-C6-alkylene optionally has 1 to 3 substituents L SA is replaced by # is the point of attachment to the heterocyclyl moiety; ## is R 6 is the attachment point to L 1 is a direct bond or C1-C6-alkylene, L 2 is a direct bond or C1-C6-alkylene, E is C3-C6-cycloalkyl or 3- to 7-membered heterocyclyl, The C3-C6-cycloalkyl and 3- to 7-membered heterocyclyl may be, in order, one to three substituents L SC optionally substituted with L SA are independently fluoro, chloro, hydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, and C-C-halocycloalkyl, or 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, L SC are independently fluoro, chloro, hydroxyl, oxo, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- alkenyl, C3-C6-cycloalkyl, or C3-C6-halocycloalkyl), R 6 is C3-C 12 -Carbocyclyl, 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; C1-C3-alkoxy and C1-C3-haloalkoxy are C3-C 12 -Carbocyclyl, C6-C 14 -substituted with one substituent selected from the group consisting of aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl; Said C3-C 12 -Carbocyclyl, C6-C 14 -aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl are each, in order, one to three R 6S optionally substituted with a substituent; C3-C 12 -Carbocyclyl, 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 each a group selected from the group consisting of 1 to 3 R 6S optionally substituted with a substituent; R 6S is halogen, cyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, 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-C 14-aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -C(=O)(OR 17 ), and -C(=O)N(R 18 )2 independently selected from the group consisting of: C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkenyl, C-C-haloalkenyl, C-C-alkynyl, C-C-haloalkynyl, C-C-alkylsulfanyl, and C-C-haloalkylsulfanyl are in turn optionally substituted by 1 to 3 substituents independently selected from the group consisting of hydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, and C-C-halocycloalkyl; and 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 with 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, and C-C-haloalkoxy; and R 17 and R 18 are independently hydrogen, C1-C4-alkyl or C1-C4-haloalkyl, said C1-C4-alkyl and C1-C4-haloalkyl in turn being optionally substituted with 1 to 3 substituents independently selected from the group consisting of hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl; The ring Y, together with the pyridine ring or pyridazine ring, represents a group represented by the formula (II-a) to the formula (II-v), respectively:

[0078] [ka] [ka]

[0079] where * is the point of attachment to the -OQ group; # is the point of attachment to another heterocycle; p is 0, 1, 2, 3, or 4; x 1 is 1 or 2, x 2 is 0, 1, or 2, R 7A , R 7B , R 7C , R 7D , R 7E , R 7F , and R 7G are independently hydrogen, hydroxyl, halogen, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, or C-C-haloalkoxy, R 7H is hydrogen, C1-C4-alkyl, or C1-C4-haloalkyl, R 7K is methylidene, halomethylidene, halogen, hydroxyl, oxo, C1-C4-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl, or 2 R's 7K the substituents, together with the carbon atoms to which they are attached, form a C3-C8-cycloalkyl ring), R 8 is hydrogen or halogen, Q is phenyl, naphthyl, C3-C 10 -carbocyclyl, 5- to 10-membered heterocyclyl, or 5- to 10-membered heteroaryl; Phenyl, naphthyl, C3-C 10 -Carbocyclyl, 5- to 10-membered heterocyclyl, and 5- to 10-membered heteroaryl optionally have 1 to 3 substituents Q S is replaced by Q Sis halogen, cyano, nitro, formyl, carboxyl, 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-ハロ independently selected from the group consisting of alkenyl, 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, and 5- or 6-membered heteroaryl, 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-ハロ alkenyl, 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 by 1 to 3 substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and 3- to 7-membered heterocyclyl, wherein the C3-C6-cycloalkyl, 3- to 7-membered heterocyclyl, phenyl, and 5- or 6-membered heteroaryl are in turn optionally substituted with 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, and C3-C6-cycloalkyl; and salts, hydrates thereof, and hydrates of said salts.

[0080] More preferably, the present invention relates to a compound of formula (I) A 2 , O, NR 1 , or CR 2A R R2B And, R 1 , R 2A , and R 2B are independently of one another hydrogen or C1-C4-alkyl, m is 0 or 1, T is hydrogen; R 3 and R 4 are independently hydrogen, fluoro, or C1-C4-alkyl, R 5 is hydrogen, L is a direct bond, methylene, monofluoromethylene, or difluoromethylene; R 6 is indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl, or dihydrobenzodioxinyl; Indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl, and dihydrobenzodioxinyl are substituted with one or two R 6S optionally substituted with a substituent; R 6Sare independently selected from the group consisting of fluoro, chloro, bromo, 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; cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl, and pyridyl are in turn optionally substituted with 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, and C-C-haloalkoxy; A 1 is N or CR 8 and R 8 is hydrogen, Q optionally contains one or two substituents Q S phenyl substituted with Q S is halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- independently selected from the group consisting of alkenyl, C2-C4-alkynyl, cyclopropyl, and cyclobutyl; said cyclopropyl and cyclobutyl are in turn optionally substituted with one or two substituents independently selected from the group consisting of fluoro and methyl; and The ring Y, together with the pyridine ring or pyridazine ring, is represented by formula (II-a), (II-b), (II-g), (II-h), (II-r), (II-s), (II-u), or (II-v), respectively:

[0081] [ka]

[0082] (In the formula, * is the point of attachment to the -OQ group, # is the point of attachment to another heterocycle; p is 0, 1, or 2; x 1 is 1 or 2, x 2 is 0, 1, or 2, R 7A is hydrogen or C1-C4-alkyl, R 7B is hydrogen, fluoro, C1-C4-alkyl or C1-C4-alkoxy, R 7C is hydrogen, fluoro, C1-C4-alkyl or C1-C4-alkoxy, R 7D is hydrogen, R 7E is hydrogen, R 7F is hydrogen, R 7K is hydroxyl, C1-C4-alkyl, or C1-C4-alkoxy, and salts, hydrates thereof, and hydrates of said salts.

[0083] Even more preferably, the present invention relates to a compound of formula (I) A 2 , O, NR 1 , or CR 2A R R2B And, R 1 , R 2A , and R 2B are independently of one another hydrogen or C1-C4-alkyl, m is 0 or 1, T is hydrogen; R 3 and R 4 are independently hydrogen, fluoro, or C1-C4-alkyl, R 5 is hydrogen, L is a direct bond, methylene, monofluoromethylene, or difluoromethylene; R 6 is indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl, or dihydrobenzodioxinyl; Indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl, and dihydrobenzodioxinyl are substituted with one or two R 6S optionally substituted with a substituent; R 6S are independently selected from the group consisting of fluoro, chloro, bromo, 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; cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl, and pyridyl are in turn optionally substituted with 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, and C-C-haloalkoxy; A 1 is N or CR 8 and R 8 is hydrogen, Q optionally contains one or two substituents Q S phenyl substituted with Q S is halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- independently selected from the group consisting of alkenyl, C2-C4-alkynyl, cyclopropyl, and cyclobutyl; said cyclopropyl and cyclobutyl are in turn optionally substituted with one or two substituents independently selected from the group consisting of fluoro and methyl; and The ring Y, together with the pyridine ring or pyridazine ring, is represented by the formula (II-a), (II-g), (II-h), or (II-r), respectively:

[0084] [ka]

[0085] (In the formula, * is the point of attachment to the -OQ group, # is the point of attachment to another heterocycle; p is 0 or 1, x 1 is 1 or 2, R 7A is hydrogen, R 7B is hydrogen or C1-C4-alkyl, R 7C is hydrogen, R 7D is hydrogen, R 7E is hydrogen, R 7F is hydrogen, R 7K is C1-C4-alkyl), and salts, hydrates thereof, and hydrates of said salts.

[0086] A 1 is preferably N or CR 8 and R 8 is hydrogen, fluoro, chloro, or bromo. Most preferably, A 1 is N or CH.

[0087] A 2 is preferably O, S, C(=O), S(=O)2, NR 1 , or CR 2AR 2B and R 1 , R 2A , and R 2B are each independently hydrogen, methyl, ethyl, n-propyl, iso-propyl, cyclopropyl, or cyclobutyl.

[0088] More preferably, A 2 is O, NR 1 , or CR 2A R 2B and R 1 , R 2A , and R 2B are each independently hydrogen, methyl, ethyl, cyclopropyl, or cyclobutyl. 2 is O, NH, or CH2.

[0089] m is preferably 0 or 1, more preferably 1.

[0090] T is preferably hydrogen or C1-C4-alkyl, more preferably hydrogen, methyl, ethyl, n-propyl or iso-propyl, most preferably hydrogen.

[0091] R 3 and R 4 are preferably independently selected from the group consisting of hydrogen, fluoro, chloro, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, and C3-C6-cycloalkyl, C1-C4-Alkyl, C2-C4-Alkenyl, and C2-C4-Alkynyl are optionally substituted by 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl; and C3-C6-Cycloalkyl is fluoro, chloro, hydroxyl, oxo, methylidene, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4-optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl; or R 3 and R 4 together with the carbon atoms to which they are attached form a C3-C6-cycloalkyl ring.

[0092] More preferably, R 3 and R 4 are independently selected from the group consisting of hydrogen, fluoro, chloro, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, and C3-C6-cycloalkyl, even more preferably from the group consisting of hydrogen, fluoro, and C1-C4-alkyl, even more preferably from the group consisting of hydrogen, fluoro, methyl, ethyl, n-propyl, and iso-propyl.

[0093] Most preferably, R 3 and R 4 are both hydrogen atoms.

[0094] R 5 is preferably hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkylsulfanyl, C-C-alkyl, C-C-alkoxy, and C-C-alkylsulfanyl are optionally substituted by 1 to 3 substituents independently selected from the group consisting of fluoro, chlorohydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, and C-C-halocycloalkyl; and C3-C6-Cycloalkyl is fluoro, chloro, hydroxyl, oxo, methylidene, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4-optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyl, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl; or R 3 and R 5 or R 4 and R 5 together with the carbon atoms to which they are attached form a C3-C6-cycloalkyl ring.

[0095] R 5 is more preferably hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, or C1-C4-alkylsulfanyl, even more preferably hydrogen, hydroxyl, or C1-C4-alkyl, even more preferably hydrogen, methyl, ethyl, n-propyl, or iso-propyl, and most preferably hydrogen.

[0096] More preferably, A 2 is O, NH, or CH, m is 0 or 1, T is hydrogen, and R 3 , R 4 , and R 5 are hydrogen atoms.

[0097] L is preferably a direct bond, C1-C6-alkylene, or a group of the formula:

[0098] [ka]

[0099] wherein the C1-C6-alkylene optionally has 1 to 3 substituents L SA is replaced by # is the point of attachment to the heterocyclyl moiety; ## is R 6 is the attachment point to L 1 is a direct bond or C1-C6-alkylene, L 2 is a direct bond or C1-C6-alkylene, E is C3-C6-cycloalkyl or 3- to 7-membered heterocyclyl, The C3-C6-cycloalkyl and 3- to 7-membered heterocyclyl may be, in order, one to three substituents L SC optionally substituted with L SA are independently fluoro, chloro, hydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, and C-C-halocycloalkyl, or 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, L SC are independently fluoro, chloro, hydroxyl, oxo, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- alkenyl, C3-C6-cycloalkyl, or C3-C6-halocycloalkyl).

[0100] L is more preferably a direct bond or C1-C6-alkylene, which may optionally contain 1 to 3 substituents L SA is replaced by L SA are independently fluoro, chloro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl.

[0101] L is even more preferably a direct bond or C1-C4-alkylene, said C1-C4-alkylene optionally containing one or two substituents L SA is replaced by L SA is independently fluoro or chloro.

[0102] L is even more preferably a direct bond, methylene, ethylene, propyl-1,3-ene, propyl-1,2-ene, butyl-1,4-ene, butyl-1,3-ene, butyl-1,2-ene, monofluoromethylene, or difluoromethylene, even more preferably a direct bond, methylene, monofluoromethylene, or difluoromethylene, and most preferably methylene.

[0103] R 6 is preferably C3-C 12 -Carbocyclyl, 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; C1-C3-alkoxy and C1-C3-haloalkoxy are C3-C 12 -Carbocyclyl, C6-C 14 -substituted with one substituent selected from the group consisting of aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl; Said C3-C 12 -Carbocyclyl, C6-C 14 -aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl are each, in order, one to three R 6S optionally substituted with a substituent; C3-C 12 -Carbocyclyl, 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 each a group selected from the group consisting of 1 to 3 R 6S optionally substituted with a substituent; R 6S is halogen, cyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, 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-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -C(=O)(OR 17 ), and -C(=O)N(R 18 )2 independently selected from the group consisting of: C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkenyl, C-C-haloalkenyl, C-C-alkynyl, C-C-haloalkynyl, C-C-alkylsulfanyl, and C-C-haloalkylsulfanyl are in turn optionally substituted by 1 to 3 substituents independently selected from the group consisting of hydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, and C-C-halocycloalkyl; and 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 with 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, and C-C-haloalkoxy; and R 17 and R 18 are independently hydrogen, C1-C4-alkyl or C1-C4-haloalkyl, The C1-C4-alkyl and C1-C4-haloalkyl are in turn optionally substituted with 1 to 3 substituents independently selected from the group consisting of hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl.

[0104] More preferably, R 6are indanyl, 1,2,3,4-tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1,3,5-trienyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indenyl, 1,2-dihydronaphthalenyl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-2,1'-tetralin]-1-yl, phenyl, naphthyl, phenoxy, benzyloxy, OCF2-phenyl, phenylsulfanyl, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothiophenyl, indolinyl, 1 ,3-benzodioxolyl, 1,2,3,4-tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, 2,3-dihydro-1,4-benzodioxinyl, 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-benzoyl Midazolyl, 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[chroman-3,1'-cyclopropan]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropan]-yl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, 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]thiophenyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl, or thieno[2,3-d]isothiazolyl; and indanyl, 1,2,3,4-tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1,3,5-trienyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indenyl , 1,2-dihydronaphthalenyl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-2,1'-tetralin]-1-yl, phenyl, naphthyl, phenoxy, benzyloxy, OCF2-phenyl, phenylsulfanyl, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, 1,2,3,4-tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, 2,3-dihydro-1,4-benzodioxinyl, 6,7-dihydrobenzoyl 4,5,6,7-tetrahydro-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-benzimidazolyl thiazothiophenyl, 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[chroman-3,1'-cyclopropan]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropanyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridinyl, pyridazinyl and pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxa linyl, 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]thiophenyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl, and thieno[2,3-d]isothiazolyl optionally have 1 to 3 substituents R, 6S is replaced by R 6S is halogen, cyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, 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-C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -C(=O)(OR 17 ), and -C(=O)N(R 18)2, wherein C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkenyl, C-C-haloalkenyl, C-C-alkynyl, C-C-haloalkynyl, C-C-alkylsulfanyl, and C-C-haloalkylsulfanyl are optionally further substituted by 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, and C-C-halocycloalkyl, as well as C-C-cycloalkylsulfanyl, C-C-cycloalkyl, C-C-cycloalkyloxy, C-C- 14 -aryl, 5- or 6-membered heteroaryl, and 3- to 7-membered heterocyclyl are optionally further substituted with 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, and C-C-haloalkoxy; and R 17 and R 18 are independently hydrogen or C1-C4-alkyl, The C1-C4-alkyl or C1-C4-haloalkyl in turn is optionally substituted with 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, and C3-C6-halocycloalkyl.

[0105] Even more preferably, R 6 is indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl, or dihydrobenzodioxinyl, and indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl, and dihydrobenzodioxinyl are substituted with one or two R 6S optionally substituted with a substituent; R 6Sare independently selected from the group consisting of fluoro, chloro, bromo, 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; Cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl, and pyridyl are in turn optionally substituted with 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, and C-C-haloalkoxy.

[0106] Even more preferably, R 6 teeth,

[0107] [ka]

[0108] (In the formula, § 1 is the point of attachment to L, R 6S1 and R 6S2 are independently hydrogen or R 6S and R 6S is halogen, cyano, C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkoxycarbonyl, C-C-alkylcarbonyl, C-C-alkenyl, C-C-alkynyl, C-C-cycloalkyl and pyrazolyl, The C3-C6-cycloalkyl and pyrazolyl are optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen and C1-C4-alkyl, R 6S1 and R 6S2 at least one of which is different from hydrogen).

[0109] Most preferably, R 6 is one or two R 6S is a phenyl substituted with a substituent, R 6S is independently selected from the group consisting of chloro, bromo, methyl, ethenyl, and pyrazolyl; The pyrazolyl is similarly substituted with one methyl substituent.

[0110] More preferably, L is methylene and R 6 is one or two R 6S phenyl substituted with R 6S is independently selected from the group consisting of chloro, bromo, methyl, ethenyl, and pyrazolyl, which is in turn substituted with one methyl substituent.

[0111] More preferably, A 2 is O, NH, or CH, m is 0 or 1, T is hydrogen, and R 3 , R 4 , and R 5 are each hydrogen, L is methylene, and R 6 is one or two R 6S phenyl substituted with R 6S is independently selected from the group consisting of chloro, bromo, methyl, ethenyl, and pyrazolyl, which is in turn substituted with one methyl substituent.

[0112] Preferably, R 7is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-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 each independently selected from 1 to 3 R 7Sa C-C-cycloalkyl and 3- to 7-membered heterocyclyl are optionally substituted by 1 to 3 R 7Sc optionally substituted with a substituent; R 20 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl, C3-C8-cycloalkyl is likewise optionally substituted by 1 or 2 substituents independently selected from the group consisting of halogen and C1-C6-alkyl, R 21 is hydroxyl, C1-C6-alkyl, or C1-C6-alkoxy, R 22 is hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, R25 and R 26 are independently hydrogen or C1-C6-alkyl, and R 7Sa are independently cyano, hydroxyl, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkyl, or C-C-alkoxycarbonyl, R 7Sc are independently halogen, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy.

[0113] More preferably, R 7 is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, -N(R 20 )2, C(=NR 21 )R 22 , or -C(=O)(OR 25 ) in which C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C2-C4-alkenyl, and C2-C4-alkynyl are selected from the group consisting of one or two R 7Sa Optionally substituted by substituents, C3-C6-cycloalkyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl are optionally substituted by one or two R 7Sc optionally substituted with a substituent; R 20 is hydrogen, C1-C4-alkyl or C3-C6-cycloalkyl, R 21 is C1-C4-alkyl or C1-C4-alkoxy, R 22 is C1-C4-alkyl, R 25is hydrogen or C1-C4-alkyl, and R 7Sa are independently C1-C4-alkoxy, R 7Sc are independently halogen or C1-C4-alkyl.

[0114] Even more preferably, R 7 is chloro, iodo, 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 And, C1-C4-Alkyl, C2-C4-alkenyl, and C2-C4-alkynyl are each independently selected from one or two R 7Sa optionally substituted with a substituent; C3-C6-cycloalkyl is one or two R 7Sc optionally substituted with a substituent; R 20 is hydrogen, cyclopropyl, or cyclobutyl; R 21 is C1-C4-alkyl or C1-C4-alkoxy, R 22 is C1-C4-alkyl, and R 7Sa are independently C1-C4-alkoxy, R 7Sc are independently halogen.

[0115] Even more preferably, R 7 is chloro, iodo, C1-C4-alkyl, difluoromethyl, trifluoromethyl, methylcarbonyl, ethylcarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, or pyrrolidinyl.

[0116] Even more preferably, R 7 is methyl, ethyl, n-propyl, or iso-propyl, and most preferably methyl.

[0117] p is preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, and most preferably 0 or 1.

[0118] More preferably, R 7 is methyl, and p is 0 or 1.

[0119] Q is preferably phenyl, naphthyl, C3-C 10 -carbocyclyl, 5- to 10-membered heterocyclyl, or 5- to 10-membered heteroaryl, including phenyl, naphthyl, C3-C 10 -Carbocyclyl, 5- to 10-membered heterocyclyl, and 5- to 10-membered heteroaryl are each 1 to 3 substituents Q S optionally substituted with Q S is halogen, cyano, nitro, formyl, carboxyl, 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-ハロ independently selected from the group consisting of alkenyl, 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, and 5- or 6-membered heteroaryl, 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-ハロ alkenyl, 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 by 1 to 3 substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C3-C6-cycloalkyl, C3-C6-halocycloalkyl and 3- to 7-membered heterocyclyl, The C3-C6-cycloalkyl, 3- to 7-membered heterocyclyl, phenyl, and 5- or 6-membered heteroaryl are in turn optionally substituted by 1 to 3 substituents independently selected from the group consisting of fluoro, chloro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxycarbonyl, C1-C4-haloalkoxycarbonyl, and C3-C6-cycloalkyl.

[0120] Q is more preferably phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydrobenzofuran ... quinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thiophenyl, or thieno[2,3-d]thiazolyl. phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl phenyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thiophenyl, and thieno[2,3-d]thiazolyl are substituted with one to three substituents Q. S optionally substituted with Q sis halogen, cyano, nitro, hydroxyl, 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- Haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C6-cycloalkyl, oxetanyl, and -N(R 43 ) 2, wherein the C3-C6-cycloalkyl and oxetanyl in turn are optionally substituted with one or two substituents independently selected from the group consisting of halogen, C1-C4-alkyl, and C1-C4-haloalkyl, and R 43 is hydrogen and C1-C6-alkyl.

[0121] Even more preferably, Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridinyl, thienyl, or indolyl, wherein phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridinyl, thienyl, and indolyl are selected from the group consisting of 1 to 3 substituents Q s optionally substituted with Q s are independently selected from the group consisting of halogen, cyano, nitro, formyl, C-C-alkyl, C-C-haloalkyl, C-C-alkylcarbonyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkenyl, C-C-alkynyl, and C-C-cycloalkyl, which C-C-cycloalkyl is in turn optionally substituted with 1 or 2 substituents independently selected from the group consisting of fluoro and methyl.

[0122] Even more preferably, Q is phenyl, wherein phenyl is selected from the group consisting of halogen, cyano, nitro, formyl, C-C-alkyl, C-C-haloalkyl, C-C-alkylcarbonyl, C-C-alkoxy, C-C-haloalkoxy, C-C-alkenyl, C-C 4- one or two substituents Q independently selected from the group consisting of alkynyl, cyclopropyl, and cyclobutyl; s wherein said cyclopropyl and cyclobutyl are in turn optionally substituted with one or two substituents independently selected from the group consisting of fluoro and methyl.

[0123] Even more preferably, Q is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C2-C 4- one or two substituents Q independently selected from the group consisting of alkenyl, C2-C4-alkynyl, and cyclopropyl; s is phenyl substituted with

[0124] Even more preferably, Q is selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, and cyclopropyl. s is phenyl substituted with

[0125] Most preferably, Q is

[0126] [ka]

[0127] (In the formula, § 2 is the point of attachment to the oxygen atom, Q S1 is hydrogen or fluoro, Q S2 is hydrogen, chloro, bromo, methyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, or cyclopropyl, while Q S1 and Q S2 at least one of which is different from hydrogen).

[0128] More preferably, A 1 is N or CH, and Q is phenyl, where phenyl is selected from the group consisting of halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C 4- one or two substituents Q independently selected from the group consisting of alkenyl, C2-C4-alkynyl, cyclopropyl, and cyclobutyl; s wherein said cyclopropyl and cyclobutyl are in turn optionally substituted with one or two substituents independently selected from the group consisting of fluoro and methyl.

[0129] Even more preferably, A 1 is N or CH, and Q is one or two substituents Q independently selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, and cyclopropyl. s is phenyl substituted with

[0130] More preferably, A 2 is O, NH, or CH, m is 0 or 1, T is hydrogen, and R 3 , R 4 , and R 5 are hydrogen, L is methylene, and R 6 is one or two R 6S phenyl substituted with R 6S is independently selected from the group consisting of chloro, bromo, methyl, ethenyl, and pyrazolyl, said pyrazolyl being in turn substituted with one methyl substituent; A 1is N or CH, and Q is one or two substituents Q independently selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, and cyclopropyl. s is phenyl substituted with

[0131] The ring Y, together with the pyridine ring or pyridazine ring, preferably represents a group represented by formula (II-a), (II-b), (II-g), (II-h), (II-r), (II-s), (II-u), or (II-v), respectively:

[0132] [ka]

[0133] (In the formula, * is the point of attachment to the -OQ group, # is the point of attachment to another heterocycle; p is 0, 1, or 2; x 1 is 1 or 2, x 2 is 0, 1, or 2, R 7A is hydrogen or C1-C4-alkyl, R 7B is hydrogen, fluoro, C1-C4-alkyl or C1-C4-alkoxy, R 7C is hydrogen, fluoro, C1-C4-alkyl or C1-C4-alkoxy, R 7D is hydrogen, R 7E is hydrogen, R 7F is hydrogen, R 7K is hydroxyl, C1-C4-alkyl, or C1-C4-alkoxy).

[0134] The ring Y is more preferably a group represented by the formula (II-a), (II-g), (II-h), or (II-r) together with the pyridine or pyridazine ring, respectively:

[0135] [ka]

[0136] (In the formula, * is the point of attachment to the -OQ group, # is the point of attachment to another heterocycle; p is 0 or 1, preferably 0; x 1 is 1 or 2, R 7A is hydrogen, R 7B is hydrogen or C1-C4-alkyl, preferably hydrogen, methyl, ethyl, n-propyl or iso-propyl, more preferably hydrogen, R 7C is hydrogen, R 7D is hydrogen, R 7E is hydrogen, R 7F is hydrogen, R 7K is C1-C4-alkyl).

[0137] More preferably, A 2 is O, NH, or CH, m is 0 or 1, T is hydrogen, and R 3 , R 4 , and R 5 are hydrogen, L is methylene, and R 6 is one or two R 6S phenyl substituted with R 6S is independently selected from the group consisting of chloro, bromo, methyl, ethenyl, and pyrazolyl, said pyrazolyl being in turn substituted with one methyl substituent; A 1is N or CH, and Q is one or two substituents Q independently selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, difluoromethyl, ethenyl, ethynyl, and cyclopropyl. s and the ring Y together with the pyridine ring or pyridazine ring represents a group of the formula (II-a), (II-g), (II-h), or (II-r), respectively:

[0138] [ka]

[0139] (In the formula, * is the point of attachment to the -OQ group, # is the point of attachment to another heterocycle; p is 0, x 1 is 1 or 2, R 7A is hydrogen, R 7B is hydrogen or C1-C4-alkyl, preferably hydrogen, methyl, ethyl, n-propyl or iso-propyl, more preferably hydrogen, R 7C is hydrogen, R 7D is hydrogen, R 7E is hydrogen, R 7F is hydrogen).

[0140] A 1 , A 2 , R 1 , R 2A , R 2B , R 3 , R 4 , R 5 , R 6 , R 7 , R 8The above specific definitions of L, m, p, T, Q, and Y (including the broad definitions, as well as the preferred, more preferred, even more preferred, and most preferred definitions) may be combined in various ways. Thus, these combinations of definitions provide subclasses of compounds according to the invention, such as those disclosed below.

[0141] Preferred are compounds of formula (I) in which each definition (substituents and variables) has the preferred meaning given above.

[0142] Particularly preferred are compounds of formula (I) in which each definition (substituents and variables) has the more, more and / or most preferred meaning given above.

[0143] The present invention also relates to any compound of formula (I) disclosed in Table 1.

[0144] The most preferred compounds of formula (I) are A 1 is N or CH, A 2 is O, NH, or CH2, m is 0 or 1, preferably 1; T is hydrogen; R 3 , R 4 , and R 5 are hydrogen, L is methylene; R 6 is one or two R 6S is a phenyl substituted with a substituent, R 6S is independently selected from the group consisting of chloro, bromo, methyl, ethenyl, and pyrazolyl; The pyrazolyl is in turn substituted with one methyl substituent; Q is one or two substituents Q S phenyl substituted with Q Sis independently selected from the group consisting of fluoro, chloro, bromo, methyl, trifluoromethyl, ethenyl, ethynyl, and cyclopropyl; and The ring Y, together with the pyridine ring or pyridazine ring, is represented by the formula (II-a), (II-g), (II-h), or (II-r), respectively:

[0145] [ka]

[0146] (In the formula, * is the point of attachment to the -OQ group, # is the point of attachment to another heterocycle; p is 0, x 1 is 1 or 2, R 7A is hydrogen, R 7B is hydrogen or methyl, R 7C is hydrogen, R 7D is hydrogen, R 7E is hydrogen, R 7F is a compound where and salts thereof, hydrates, and hydrates of said salts.

[0147] The compounds of formula (I) can be used as fungicides (for controlling plant pathogenic fungi), in particular in methods for controlling plant pathogenic fungi which comprise applying one or more compounds of formula (I) to plants, plant parts, seeds, fruit, or the soil in which the plants are growing.

[0148] Processes for preparing compounds of formula (I) and intermediates The present invention also relates to processes for preparing compounds of formula (I) and intermediates thereof. Unless otherwise indicated, the variables A used below 1 , A 2 , R1 , 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 product of formula (I), but also to all intermediates containing the respective variables.

[0149] 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). All variables in formula (Ia) and formulas (Ia-1) to (Ia-3) are as defined above for formula (I) unless otherwise specified.

[0150] The compounds of formula (I) can be prepared by a variety of routes, as well as by known processes. Non-limiting examples of suitable processes are described herein.

[0151] A compound of formula (I) may be obtained directly by carrying out one of the processes A-E outlined below, or may be obtained by conversion or derivatization of another compound of formula (I) prepared according to the processes described herein. For example, a compound of formula (I) may be converted to another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) with other substituents.

[0152] The processes described herein can be suitably carried out using one or more inert organic solvents customary 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, ligroin, benzene, toluene, xylene, or decalin), 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 t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, or anisole), ketones (e.g., acetone, methyl ethyl ketone, methyl isopropyl ether, methyl ...methyl ether, methyl methyl methyl ether, methyl methyl methyl ether, methyl methyl methyl ether, methyl methyl methyl ether, methyl methyl methyl ether, methyl methyl methyl ether, methyl methyl methyl methyl ether, methyl methyl methyl methyl ether, methyl methyl methyl methyl methyl methyl methyl methyl methyl methyl methyl methyl The solvent may be any of the following: an isopropyl ketone, and methyl isobutyl ketone), an ester (e.g., methyl acetate, ethyl acetate, or butyl acetate), an alcohol (e.g., methanol, ethanol, propanol, isopropanol, butanol, tert-butanol), a nitrile (e.g., acetonitrile, propionitrile, n- or i-butyronitrile, or benzonitrile), an amide (e.g., N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone, or hexamethylphosphoric triamide), a sulfoxide (e.g., dimethyl sulfoxide) or a sulfone (e.g., sulfolane), a urea (e.g., 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone), or a mixture thereof.

[0153] Some processes described herein require or can optionally use one or more inorganic or organic bases customary for such reactions. Examples of suitable inorganic and organic bases include alkaline earth metal 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 metal or alkali metal hydroxides (e.g., sodium hydroxide, calcium hydroxide, potassium hydroxide, or other ammonium hydroxide derivatives), alkaline earth metal, alkali metal, or ammonium fluorides (e.g., potassium fluoride, cesium fluoride, or tetrabutylammonium fluoride), alkali metal or alkaline earth metal acetates (e.g., sodium acetate, lithium acetate, potassium acetate, or calcium acetate), alkali metals, Examples of suitable bases include, but are not limited to, alcoholates (e.g., potassium tert-butoxide or sodium tert-butoxide), alkali metal phosphates (e.g., tripotassium phosphate), tertiary amines (e.g., 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 (e.g., pyridine, picoline, lutidine, or collidine).

[0154] Some of the processes described herein can optionally be carried out in the presence of a transition metal catalyst, such as a metal (e.g., copper or palladium) salt or complex, and, where appropriate, in the presence of a ligand.

[0155] Suitable copper salts or complexes and hydrates thereof include, but are not limited to, metallic copper, 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, bis(2,2,6,6-tetramethyl-3,5-heptanedionate)copper(II), copper(II) trifluoromethanesulfonate, tetrakis(acetonitrile)copper(I) hexafluorophosphate, tetrakis(acetonitrile)-copper(I) tetrafluoroborate.

[0156] The appropriate copper complex can be prepared in situ in the reaction mixture by adding copper salts and ligands or salts separately, such as: It is also possible to generate in situ: ethylenediamine, N,N-dimethylethylenediamine, N,N'-dimethylethylenediamine, rac-trans-1,2-diaminocyclohexane, rac-trans-N,N'-dimethylcyclohexane-1,2-diamine, 1,1'-binaphthyl-2,2'-diamine, N,N,N',N'-tetramethylethylenediamine, proline, N,N-dimethylglycine, quinolin-8-ol, pyridine, 2-aminopyridine, 4-(dimethylamino)pyridine, 2,2'-bipyridyl, 2,6-di(2-pyridyl)pyridine, 2-picolinic acid, 2-(dimethylaminomethyl)-3-hydroxypyridine, 1,10-phenanthroline, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-dimethyl-1,10-phenanthroline, 4,7-dimethoxy-1,10 -phenanthroline, N,N'-bis[(E)-pyridin-2-ylmethylidene]cyclohexane-1,2-diamine, N-[(E)-phenylmethylidene], N-[(E)-phenylmethylidene]-cyclohexanamine, 1,1,1-tris(hydroxymethyl)ethane, n-butylimidazole, ethylene glycol, 2,2,6,6-tetramethylheptane-3,5-dione, 2-(2,2-dimethylpropanoyl)cyclohexanone, acetylacetone, dibenzoylmethane, 2-(2-methylpropanoyl)cyclohexanone, biphenyl-2-yl(di-tert-butyl)phosphane, ethylene bis-(diphenylphosphine), N,N-diethylsalicylamide, 2-hydroxybenzaldehyde oxime, oxo[(2,4,6-trimethylphenyl)amino]acetic acid, or 1H-pyrrole-2-carboxylic acid.

[0157] 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]dichloropalladium(II), bis(cinnamyl)dichlorodipalladium(II), bis(allyl)-dichlorodipalladium(II), or [1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II).

[0158] Palladium complexes can also be formed in the reaction mixture by adding separately to the reaction palladium salts and ligands or salts such as: triethylphosphine, tri-tert-butylphosphine, tri-tert-butylphosphonium 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'-diisopropoxybiphenyl, triflate phenyl-phosphine, tris-(o-tolyl)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) (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.

[0159] Suitable catalysts and / or ligands may be selected from commercial catalogs or reviews such as "Metal Catalysts for Organic Synthesis" by Strem Chemicals (Chemical Society Reviews (2014), 43, 3525, Coordination Chemistry Reviews (2004), 248, 2337 and references therein).

[0160] Some of the processes described herein can be carried out by metal photoredox catalysis according to methods reported in the literature (Nature chemistry review, (2017) 0052 and references cited 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). This process is then carried out in the presence of a photosensitizer, such as an Ir complex and a Ru complex or an organic dye, and a metal catalyst, such as a Ni complex. The reaction can be carried out in the presence of a ligand, and, where appropriate, a base, under irradiation with blue or white light.

[0161] Suitable photosensitizers include [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(tetramephene) )PF6 (diF(5-Me)ppy = 2-(2,4-difluorophenyl)-5-methylpyridine, tetramephen = 3,4,7,8-tetramethyl-1,10-phenanthroline), rubidium (Ru)(II) photocatalysts such as Ru(bpy)3Cl2 or Ru(bpy)3(PF6)2, or organic dyes such as 9-mesityl-10-acridinium perchlorate or tetrafluoroborate, or 2,4,5,6-tetra-9H-carbazol-9-yl-1,3-benzenedicarbonitrile, 9-fluorenone, and 9,10-phenanthrenequinone.

[0162] 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, and nickel(II) nitrate hexahydrate. These nickel catalysts may be used in combination with bipyridine ligands such as 2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine, and 4,4'-dimethyl-2,2'-bipyridine, or phenanthrolines such as 1,10-phenanthroline, 4,7-dimethyl-1,10-phenanthroline, and 4,7-dimethoxy-1,10-phenanthroline, or diamines such as N,N,N',N'-tetramethylethylenediamine, or diones such as tetramethylheptanedione.

[0163] The processes described herein can be carried out at temperatures ranging from -105°C to 250°C, preferably from -78°C to 185°C.

[0164] The reaction time varies as a function of the scale of the reaction and the reaction temperature, but is generally from a few minutes to 48 hours.

[0165] The processes described herein are generally carried out under normal pressure, however, it is also possible to work under elevated or reduced pressure.

[0166] In the processes described herein, the starting materials are generally used in approximately equimolar amounts, although it is also possible to use one of the starting materials in relatively large excess.

[0167] Process for preparing compounds of formula (I) Process A Formula (Ia-1) (where A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7, and Q are defined as above, A 2 is O, T is hydrogen, and m is 1 or 2), Formula (4):

[0168] [ka]

[0169] (In the formula, m, A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , and Q are defined as above, and W is hydrogen or an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl), by cyclizing the compound 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) can be prepared as shown in Scheme 1 by treating the compound of formula (4) with a dehydrating agent, optionally in the presence of a base, followed by a deprotection step to give the compound of formula (Ia-1).

[0170] [ka]

[0171] The compound of formula (Ia-1) can be obtained by treating the compound of formula (4) with a dehydrating agent such as phosphoryl chloride (POCl), diphosphorus pentoxide (PO), or triflic anhydride, optionally in the presence of a base. Such methods for forming the oxadiazine ring are known and are described in the literature (J. Med. Chem. 2017, 60, 2383-2400). The reaction can be carried out in a conventional inert organic solvent. It is preferable to use optionally halogenated aliphatic, alicyclic, or aromatic hydrocarbons (petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane, etc.), ethers (diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, anisole, etc.), nitriles (acetonitrile, propionitrile, n- or i-butyronitrile, or benzonitrile), alcohols (ethanol or isopropanol).

[0172] If 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 in Organic Synthesis; Peter GM Wuts; Wiley; Fifth Edition; 2014; 895-1194). For example, a tert-butoxycarbonyl group can be removed in an acidic medium such as hydrochloric acid or trifluoroacetic acid.

[0173] The compound of formula (4) can be prepared by first reacting a compound of formula (1) 1 , ring Y, p, R 7 , and Q is defined as above, U 1 is hydroxyl, halogen, or C1-C6-alkoxy) Formula (2) (where m, R 3 , R4 , R 5 , L, and R 6 is defined as above, W is hydrogen or an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl; or a salt thereof to form a compound represented by formula (3) (wherein m, A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , Q, and W are defined as above, excluding the phthalimide group), to provide a compound of formula (4).

[0174] 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; Fifth Edition; 2014; 1012-1014).

[0175] Compounds of formula (1) may be prepared by one or more of the processes described herein (see Processes F to M outlined below).

[0176] Amines of formula (2) may be prepared by process O described herein.

[0177] U 1Compounds of formula (1) in which is a hydroxyl group can be reacted with amines of formula (2) in the presence of a condensing reagent by methods described in the literature (e.g., Tetrahedron 2005, 61, 10827-10852). Examples of suitable condensing reagents include halogenating agents (e.g., phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride, or thionyl chloride), dehydrating reagents (e.g., ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, or methanesulfonyl chloride), carbodiimides (e.g., N,N'-dicyclohexylcarbodiimide (DCC)), or other conventional condensing (or peptide bond) reagents (e.g., phosphorus pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 1-[bis(dimethyl amino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), N,N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, bromotripyrrolidinophosphonium hexafluorophosphate, or propanephosphonic anhydride (T3P).

[0178] U 1 Compounds of formula (1) in which is a halogen atom can be reacted with amines of formula (2) in the presence of an acid scavenger by well-known methods. Suitable acid scavengers include any inorganic and organic bases conventional for such reactions, as described herein. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic bases are preferred.

[0179] U 1 Compounds of formula (1) in 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 trimethylaluminum.

[0180] Process B Formula (Ia-1) (where A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , and Q are defined as above, A 2 is O, T is hydrogen; m is 1 or 2) also includes Formula (7):

[0181] [ka]

[0182] (In the formula, m, A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, and R 7 is defined as above, W is hydrogen or an amino protecting group, preferably hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl, more preferably hydrogen; and X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, Formula (8):

[0183] [ka]

[0184] where Q is defined as above, 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.

[0185] [ka]

[0186] The compound of formula (7) is a compound of formula (5) (wherein A 1 , ring Y, p, and R 7 is defined as above, X is halogen, preferably bromo, and U 1 is hydroxyl, halogen, or C1-C6-alkoxy) Formula (2) (where m, R 3 , R 4 , R 5 , L, and R 6 is defined as above, W is hydrogen or an amino protecting group, preferably tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl. or a salt thereof to form a compound represented by formula (6a) (wherein m, A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , X, and W are defined as above, and G is a phthalimide compound or a salt thereof, and removing the phthalimide group from the compound of formula (6a) to form a compound of formula (6b): 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , X, and W are defined as above, and G is NH2), subsequently, when W is hydrogen, treating said compound of formula (6b) with a dehydrating agent, optionally in the presence of a base, to directly obtain a compound of formula (7); or When W is an amino protecting group, it may be prepared by treating the compound of formula (6b) above with a dehydrating agent, optionally in the presence of a base, and finally deprotecting to give a compound of formula (7) under the same conditions as described herein for Process A.

[0187] The reaction of a compound of formula (7) with a compound of formula (8) may 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.

[0188] Compounds of formula (5) are commercially available or can be prepared by process N described herein.

[0189] Compounds of formula (8) are commercially available or may be obtained by converting or derivatizing other compounds of formula (8) according to well-known methods.

[0190] Process C Formula (Ia-1) (where A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , and Q are defined as above, A 2 is O, T is hydrogen; m is 1 or 2; and Formula (Ia-2) (where A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , and Q are defined as above, A 2 is NH, T is hydrogen; m is 1 or 2), - reacting a compound of formula (10) with a compound of formula (11a) to provide a compound of formula (12), -E1 and E 2 is hydroxyl, converting said compound of formula (12-a) to a compound of formula (Ia-1) using Mitsunobu reaction conditions known to those skilled in the art (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kurti, Barbara Czako; Elsevier; 2005; 294-295 and references therein); -E 1 is halogen and E 2 is hydroxyl, converting the compound of formula (12) into a compound of formula (Ia-1) in the presence of a base; or - reacting a compound of formula (10) with a compound of formula (11b) to provide a compound of formula (13), -E 1 is halogen and E 2 is amino, converting the compound of formula (13) into a compound of formula (Ia-2) in the presence of a base; It can be prepared as shown in Scheme 3 by a process comprising:

[0191] E 1 Compounds of formula (9) where E = hydroxyl are commercially available or can be synthesized by methods described in the literature (Molecules, 9 (6), 405-426; 2004, International Publication No. 2017203474). 1 Compounds of formula (9) where E = halogen can be obtained by the corresponding amino alcohols, i.e. 1 = hydroxyl can be obtained by well-known methods from compounds of formula (9).

[0192] [ka]

[0193] Process D Formula (Ia-1) (where A 1 , R3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , and Q are defined as above, A 2 is O, T is hydrogen; m is 1 or 2), - reacting a compound of formula (14) with a compound of formula (11a) to provide a compound of formula (15), -E 1 is hydroxyl and E 2 is hydroxyl, converting said compound of formula (15) to a compound of formula (7) using Mitsunobu reaction conditions known to those skilled in the art (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kurti, Barbara Czako; Elsevier; 2005; 294-295 and references therein); -E 1 is halogen and E 2 is hydroxyl, converting said compound of formula (15) to a compound of formula (7) in the presence of a base; - as in step B, can be prepared as shown in scheme 4 by a process comprising reacting a compound of formula (7) with a compound of formula (8) in the presence of a base (for example an organic or inorganic base), optionally in the presence of a suitable copper salt or complex.

[0194] [ka]

[0195] If W represents an amino protecting group, step 3 can be followed by an additional deprotection step using reaction conditions described in the literature (Greene's Protective Groups in organic Synthesis; Peter GM Wuts; Wiley; Fifth Edition; 2014; 895-1194) to provide compounds of formula (Ia-1).

[0196] Formula (9) (where E 1 = hydroxyl) is commercially available or can be synthesized by the method described in the literature (Molecules, 9 (6), 405-426; 2004, WO 2017203474). 1 Compounds of formula (9) where E = halogen can be obtained by the corresponding amino alcohols, i.e. 1 = hydroxyl can be obtained by well-known methods from compounds of formula (9).

[0197] Process E Formula (Ia-3) (where A 1 , R 5 , L, R 6 , ring Y, p, R 7 , and Q are defined as above, A 2 is CR 2A R 2B and T is hydrogen; m is 0) Formula (1) (where A 1 , ring Y, p, R 7 , and Q is defined as above, U 1 is hydroxyl or halogen) Formula (16) (where R 2A , R 2B , R 5 , L, and R 6 can be prepared as shown in Scheme 5 by reacting the compound with a diamine of formula (wherein R is defined as above).

[0198] [ka]

[0199] Process E can be carried out in the presence of a dehydrating agent such as phosphoryl chloride (POCl3).

[0200] Diamines of formula (16) are 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; WO 2009003867).

[0201] Process for preparing compounds of formula (1) Compounds of formula (1) may be obtained directly by performing one of the processes described below, or may be obtained by conversion or derivatization of another compound of formula (1) prepared according to the processes described herein. Compounds of formula (1-a) through formula (1-f) are various subsets of formula (1); compounds of formula (1-a1) and formula (1-a2) are various subsets of formula (1-a); and compounds of formula (1-b1) and formula (1-b2) are various subsets of formula (1-b).

[0202] Process F Formula (1-a1) (wherein Q is defined as above, U 1 is hydroxyl or C1-C6-alkoxy, Y 1 , Y 2 , Y 3 , and Y 4 are independently N, CH, or CR 7 and R 7 is defined as above, and the variable Y 1 , Y 2 , Y 3 , and Y 4 where not more than three of the Equation (19) (where Q is defined as above, Y1 , Y 2 , Y 3 , and Y 4 are independently N, CH, or CR 7 and R 7 is defined as above, and the variable Y 1 , Y 2 , Y 3 , and Y 4 Not more than three of are N, and X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, Carbon monoxide, carbon dioxide, or formula (20) (In the formula, E 3 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy, and U 2 can be prepared as shown in Scheme 6 by reacting with a reagent (which is C1-C6-alkoxy).

[0203] [ka]

[0204] Compounds of formula (17) are commercially available or can be prepared according to methods described in the literature (WO 2012162254, WO 2010116084).

[0205] Compounds of formula (8) are commercially available or may be obtained by converting or derivatizing other compounds of formula (8) according to well-known methods.

[0206] The compound of formula (19) can be prepared by reacting a compound of formula (17) (wherein Y 1 , Y 2 , Y 3 , and Y 4 are independently N, CH, or CR 7 and R 7 is defined as above, and the variable Y 1 , Y 2 , Y 3 , and Y4 Not more than three of are N, and X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, The compound of formula (17) is reacted with a compound of formula (8) (wherein Q is defined as above) in the presence of a suitable transition metal catalyst salt or complex as described herein to produce a compound of formula (18) (wherein Q is defined as above, and (In the formula, Y 1 , Y 2 , Y 3 , and Y 4 are independently N, CH, or CR 7 and R 7 is defined as above, and the variable Y 1 , Y 2 , Y 3 , and Y 4 wherein not more than three of the groups are N, The compound of formula (18) can be prepared by converting it to a compound of formula (19) in the presence of a halogenating reagent such as phosphoryl chloride (POCl), phosphoryl bromide (POBr), phosphorus trichloride (PCl), or phosphorus tribromide (PBr) (see WO2012162254).

[0207] The compound of formula (1-a1) can be prepared by reacting a compound of formula (19) with n-butyllithium (nBuLi) and carbon dioxide or a reagent of formula (20), or - can be prepared by treatment with carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0208] Process G Formula (1-a2) (wherein Q is defined as above, U 1 is hydroxyl or C1-C6-alkoxy, Y 5 , Y 6 , and Y 7 are independently O, S, N, CH, or CR7 and R 7 is defined as above, and the variable Y 5 , Y 6 , and Y 7 where no more than two of the atoms are heteroatoms, Equation (23) (where Q is defined as above) Y 5 , Y 6 , and Y 7 are independently O, S, N, CH, or CR 7 and R 7 is defined as above, and the variable Y 5 , Y 6 , and Y 7 Not more than two of are heteroatoms, and X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, Carbon monoxide, carbon dioxide, or formula (20) (In the formula, E 3 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy, and U 2 can be prepared as shown in Scheme 6 by reacting with a reagent (which is C1-C6-alkoxy).

[0209] [ka]

[0210] Compounds of formula (21) are commercially available or can be prepared by methods described in the literature (WO 2017133667; J. Org. Chem. 2004, 79, 10311-10322; Monatshefte fur Chemie 1986, 117, 221-230).

[0211] The compound of formula (23) can be prepared by reacting a compound of formula (21) (wherein Y 5 , Y 6 , and Y 7are independently O, S, N, CH, or CR 7 and R 7 is defined as above, and the variable Y 5 , Y 6 , and Y 7 Not more than two of are heteroatoms, and X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, with a reagent of formula (8) (wherein Q is defined as above), Reaction in the presence of a base, and optionally in the presence of a suitable transition metal catalyst salt or complex as described herein, affords a compound of formula (22), wherein Q is defined as above, and

[0212] Y 5 , Y 6 , and Y 7 are independently O, S, N, CH, or CR 7 and R 7 is defined as above, and the variable Y 5 , Y 6 , and Y 7 wherein not more than two of the heteroatoms are heteroatoms, and The compound of formula (22) is treated with a halogenating reagent such as bromine, iodine, NCS (N-chlorosuccinimide) or NBS (N-bromosuccinimide) in the presence of a base as described herein to give a compound of formula (23), wherein Q is defined as above:

[0213] Y 5 , Y 6 , and Y 7 are independently O, S, N, CH, or CR 7 and R 7 is defined as above, and the variable Y 5 , Y 6 , and Y 7 Not more than two of are heteroatoms, and X can be prepared by forming a compound of a halogen, preferably fluoro, chloro, or bromo, more preferably bromo.

[0214] The compound of formula (1-a2) can be prepared by reacting a compound of formula (23) with a base (for example n-butyllithium (nBuLi)) and carbon dioxide or a reagent of formula (20), or - can be prepared by treatment with carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0215] Process H Formula (1-b1) (wherein Q and R 8 is defined as above, U 1 is hydroxyl or C1-C6-alkoxy, Y 1 , Y 2 , Y 3 , and Y 4 are independently N, CH, or CR 7 and R 7 is defined as above, and the variable Y 1 , Y 2 , Y 3 , and Y 4 where not more than three of the Formula (26) (wherein Q and R 8 is defined as above, Y 1 , Y 2 , Y 3 , and Y 4 are independently N, CH, or CR 7 and R 7 is defined as above, and the variable Y 1 , Y 2 , Y 3 , and Y 4 Not more than three of are N, and X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, Carbon monoxide, carbon dioxide, or formula (20) (In the formula, E 3 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy, and U 2 can be prepared as shown in Scheme 8 by reacting with a reagent (which is C1-C6-alkoxy).

[0216] [ka]

[0217] Compounds of formula (24) are commercially available or can be prepared according to methods described in the literature (WO 2012162254, WO 2010116084).

[0218] Compounds of formula (8) are commercially available or may be obtained by converting or derivatizing other compounds of formula (8) according to well-known methods.

[0219] The compound of formula (26) can be prepared by reacting a compound of formula (24) (wherein R 8 is defined as above, Y 1 , Y 2 , Y 3 , and Y 4 are independently N, CH, or CR 7 and R 7 is defined as above, and the variable Y 1 , Y 2 , Y 3 , and Y 4 3 or less of the X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, and W 1 is hydrogen or benzyl) compound, The compound of formula (24) is reacted with a reagent of formula (8) (wherein Q is defined above) in the presence of a suitable transition metal catalyst salt or complex as described herein to give a compound of formula (25) (wherein Q and R 8 is defined as above, Y 1 , Y 2 , Y 3 , and Y 4are independently N, CH, or CR 7 and R 7 is defined as above, and the variable Y 1 , Y 2 , Y 3 , and Y 4 Not more than three of are N, and W 1 forms a compound with hydrogen or benzyl), and converting the compound of formula (25) into a compound of formula (26): -W 1 If is hydrogen, it can be directly converted in the presence of a dehydrating reagent such as phosphoryl chloride (POCl3), phosphoryl bromide (POBr3), phosphorus trichloride (PCl3), or phosphorus tribromide (PBr3), -W 1 When W is benzyl, the compound of formula (25) (wherein W 1 is hydrogen), and then converting the resulting compound to a compound of formula (26) in the presence of a dehydrating reagent such as phosphoryl chloride (POCl3), phosphoryl bromide (POBr3), phosphorus trichloride (PCl3), or phosphorus tribromide (PBr3).

[0220] The compound of formula (1-b1) can be prepared by reacting a compound of formula (26) with n-butyllithium (nBuLi) and carbon dioxide or a reagent of formula (20), or - can be prepared by treatment with carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0221] Process I Formula (1-b2) (wherein Q and R 8 is defined as above, U 1 is hydroxyl or C1-C6-alkoxy, (In the formula, Y 5 , Y 6 , and Y 7 are independently O, S, N, CH, or CR 7 and R 7is defined as above, and the variable Y 5 , Y 6 , and Y 7 where no more than two of the atoms are heteroatoms, Formula (29) (wherein Q and R 8 is defined as above, Y 5 , Y 6 , and Y 7 are independently O, S, N, CH, or CR 7 and R 7 is defined as above, and the variable Y 5 , Y 6 , and Y 7 Not more than two of are heteroatoms, and X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, Carbon monoxide, carbon dioxide, or a compound represented by formula (20) (wherein E 3 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy, and U 2 The compounds may be prepared as shown in Scheme 9 by reacting with a reagent of the formula:

[0222] [ka]

[0223] Compounds of formula (27) are commercially available or can be prepared according to methods described in the literature (WO2005095401, WO2018067422, WO2016106106, WO2014144455, WO2013086397).

[0224] The compound of formula (29) can be prepared by reacting a compound of formula (27) (wherein R 8 is defined as above, Y 5 , Y 6 , and Y 7 are independently O, S, N, CH, or CR7 and R 7 is defined as above, and the variable Y 5 , Y 6 , and Y 7 at most two of the X is halogen, preferably fluoro, chloro, or bromo, more preferably bromo, and W 1 is hydrogen or benzyl) compound, with a reagent of formula (8) (wherein Q is defined as above), Reaction in the presence of a suitable transition metal catalyst salt or complex as described herein provides a compound of formula (28), where Q and R 8 is defined as above, Y 5 , Y 6 , and Y 7 are independently O, S, N, CH, or CR 7 and R 7 is defined as above, and the variable Y 5 , Y 6 , and Y 7 Not more than two of are heteroatoms, and W 1 forms a compound with hydrogen or benzyl), and converting the compound of formula (28) into a compound of formula (29): -W 1 If is hydrogen, it can be directly converted in the presence of a dehydrating reagent such as phosphoryl chloride (POCl3), phosphoryl bromide (POBr3), phosphorus trichloride (PCl3), or phosphorus tribromide (PBr3), -W 1 When W is benzyl, the compound of formula (28) (wherein W 1 is hydrogen), and then converting the resulting compound to a compound of formula (26) in the presence of a dehydrating reagent such as phosphoryl chloride (POCl3), phosphoryl bromide (POBr3), phosphorus trichloride (PCl3), or phosphorus tribromide (PBr3).

[0225] The compound of formula (1-b2) can be prepared by reacting a compound of formula (29) with n-butyllithium (nBuLi) and carbon dioxide or a reagent of formula (20), or - can be prepared by treatment with carbon monoxide and an alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0226] Process J Formula (1-c) (wherein Q and R 7 is defined as above, U 1 is hydroxyl or C1-C6-alkoxy, Y 8 is O, S or NY', Y' is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl, and x 3 is 1, 2, or 3) Formula (33) (wherein Q, p, and R 7 is defined as above, Y 8 is O, S or NY', Y' is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl, and x 3 is 1, 2, or 3), Carbon dioxide, or formula (20) (In the formula, E 3 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy, and U 2 The compounds may be prepared as shown in Scheme 10 by reacting with a reagent of the formula:

[0227] [ka]

[0228] Compounds of formula (30) and formula (31) are commercially available.

[0229] Compounds of formula (8) are commercially available or may be obtained by converting or derivatizing other compounds of formula (8) according to well-known methods.

[0230] A compound of formula (33) can be prepared from a compound of formula (30) by reacting said 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 said 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).

[0231] 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).

[0232] Process K Formula (1-d) (where Q, p, R 7 , and R 8 is defined as above, U 1 is hydroxyl or C1-C6-alkoxy, Y 8 is O, S or NY', Y' is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl, and x 3 is 1, 2, or 3) Formula (36) (where Q, p, R 7 , and R 8 is defined as above, Y 8 is O, S or NY', Y' is hydrogen, C1-C6-alkyl or C3-C6-cycloalkyl, and x 3 is 1, 2, or 3), Carbon dioxide, or formula (20) (In the formula, E 3is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy, and U 2 The compounds may be prepared as shown in Scheme 11 by reacting with a reagent such as (wherein is C1-C6-alkoxy).

[0233] [ka]

[0234] Compounds of formula (31) and formula (34) are commercially available.

[0235] Compounds of formula (8) are commercially available or may be obtained by converting or derivatizing other compounds of formula (8) according to well-known methods.

[0236] A compound of formula (36) can be prepared from a compound of formula (34) by reacting said 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 (35), and reacting said 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).

[0237] 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).

[0238] Process L Formula (1-e) (wherein Q and R 7 is defined as above, U 1 is hydroxyl or C1-C6-alkoxy, Y 1 is O, S, S(=O)2, CH, or CR 7 and R 7 is defined as above, x 1is 1 or 2, and x 2 is 1, 2, or 3) Equation (38) (where Q is defined as above) U 1 is hydroxyl or C1-C6-alkoxy, and X is a halogen Formula (39) (wherein p and R 7 is defined as above, x 1 is 1 or 2, and x 2 is 1, 2, or 3), and They may be prepared as shown in Scheme 12 by reaction in the presence of a metal photoredox catalyst described herein and a base (eg, an organic or inorganic base).

[0239] [ka]

[0240] Compounds of formula (38) can be prepared by reacting compounds of formula (37) with a reagent of formula (8) in the presence of a base, optionally in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0241] The compound of formula (37) is commercially available.

[0242] Compounds of formula (8) are commercially available or may be obtained by converting or derivatizing other compounds of formula (8) according to well-known methods.

[0243] Process M Formula (1-f) (wherein Q, ring Y, p, and R 7 is defined as above, and U 1 is C1-C6-alkoxy) Formula (5-a) (wherein rings Y, p, and R 7is defined as above, U 1 is C1-C6-alkoxy, and X is a halogen A reagent of formula (8) (wherein Q is defined as above), They may also be prepared as shown in Scheme 13 by reacting in the presence of a base (eg, an organic or inorganic base), optionally in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0244] [ka]

[0245] Compounds of formula (5-a) can be prepared from compounds of formula (43) in the presence of a halogenating reagent such as phosphoryl chloride (POCl), phosphoryl bromide (POBr), phosphorus trichloride (PCl), or phosphorus tribromide (PBr).

[0246] The compound of formula (43) can be prepared from the compounds of formula (40) and formula (41) by a method described in the literature (WO 2018125800).

[0247] Formula (1-a), Formula (1-b), Formula (1-c), Formula (1-d), Formula (1-e), and Formula (1-f) (wherein U 1 is C1-C6-alkoxy) can be converted to compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) (wherein U is C1-C6-alkoxy) by well-known functional group interconversion methods, for example, by hydrolysis of the ester group with lithium hydroxide (LiOH) in tetrahydrofuran / water. 1 is a hydroxyl group).

[0248] Formula (1-a), Formula (1-b), Formula (1-c), Formula (1-d), Formula (1-e), and Formula (1-f) (wherein U 1is hydroxyl), can be prepared by a known method in the presence of a halogenating agent, by a method of formula (1-a), formula (1-b), formula (1-c), formula (1-d), formula (1-e), and formula (1-f) (wherein U 1 is a halogen. Suitable halogenating reagents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride, oxalyl chloride, and thionyl chloride.

[0249] Process for preparing compounds of formula (5) Compounds of formula (5-a) are various subsets of formula (5).

[0250] Process N Formula (5) (where A 1 , ring Y, p, and R 7 is defined as above, U 1 is hydroxyl or C1-C6-alkoxy, and X is a halogen Formula (44) (where A 1 , ring Y, p, and R 7 is defined above, and X is a halogen A base and carbon dioxide or a compound of formula (20) (In the formula, E 3 is halogen, cyano, C1-C6-alkoxy or C1-C6-alkoxycarbonyloxy, and U 2 The compounds may be prepared as shown in Scheme 14 by reacting with a reagent such as (wherein is C1-C6-alkoxy).

[0251] [ka]

[0252] The compound of formula (44) is commercially available or has been described in the literature (WO 2017004500, WO 2017112719, WO 2016115272, WO 2011015343, WO 2017023905, WO 2017112678, Monatshefte fur Chemie 2018, 149, 1857-1864, WO 2005095401, WO 2018067422, WO 2016106106, WO 2014144455, WO 2013086397, WO 20140121198, WO 2011145287, WO 2012098387, Eur. J. Med. Chem. 2017, 138, 816-829).

[0253] Compounds of formula (20) are commercially available.

[0254] Process for preparing compounds of formula (2) and formula (9) The compounds of formula (9-a) and formula (9-b) are various subsets of formula (9) Process O Formula (9-a) (where L, R 3 , R 4 , R 5 , and R 6 is defined as above, m is 1 or 2, and W is hydrogen or an amino protecting group, preferably hydrogen, tert-butoxycarbonyl, benzyl, aryl, or (4-methoxyphenyl)methyl), They may be converted to the corresponding compounds of formula (2) or (9-b) as shown in Scheme 15 by methods described in the literature.

[0255] [ka]

[0256] The amino functionality of compounds of formula (9-a) where W is hydrogen can be first protected according to known methods to provide compounds of formula (9-a) where 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).

[0257] Compounds of formula (9-a) can then be converted to compounds of formula (2) using conventional Mitsunobu reaction conditions known to those skilled in the art (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kurti, Barbara Czako; Elsevier; 2005; 294-295 and references therein).

[0258] E 1 The compound of formula (9-a) in which E is hydroxyl can be prepared by a known method in the presence of a halogenating agent by reacting E 1 is a halogen. Suitable halogenating reagents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride, oxalyl chloride, and thionyl chloride.

[0259] The amino alcohol of formula (9-a) (wherein W = hydrogen) is commercially available or can be prepared by a method described in the literature (Molecules, 9 (6), 405-426; 2004, WO 2017203474).

[0260] Intermediates The present invention also relates to intermediates for preparing compounds of formula (I).

[0261] Formula (1):

[0262] [ka]

[0263] (In the formula, A 1 , Q, ring Y, p, and R 7 is defined as in formula (I), and U 1 is hydroxyl, halogen, or C1-C6-alkoxy) It is a key intermediate for the preparation of compounds of formula (I).

[0264] A given with respect to formula (I) 1 , Q, ring Y, p, and R 7 The definitions of preferred, more preferred, even more preferred and most preferred apply mutatis mutandis.

[0265] U 1 is preferably hydroxyl, fluoro, chloro, bromo, methoxy, ethoxy, or tert-butoxy.

[0266] Also, equation (2):

[0267] [ka]

[0268] (In the formula, L, R 5 , and R 6 is defined as in formula (I), m is 1 or 2, preferably 1; R 3 and R 4 are independently hydrogen, halogen, or C1-C6-alkyl, or R 3 and R 4 together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl ring, and W is hydrogen or an amino protecting group, preferably hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl), It is a key intermediate for the preparation of compounds of formula (I).

[0269] L, R as given for formula (I) 5 , and R 6 The definitions of preferred, more preferred, even more preferred and most preferred apply mutatis mutandis.

[0270] R 3 and R 4 are preferably independently selected from the group consisting of hydrogen, fluoro, chloro, and C1-C4-alkyl, more preferably from the group consisting of hydrogen, fluoro, and C1-C4-alkyl, even more preferably from the group consisting of hydrogen, fluoro, methyl, ethyl, n-propyl, and iso-propyl. Most preferably, R 3 and R 4 are both hydrogen atoms.

[0271] The present invention also provides compounds of formula (3) and formula (4):

[0272] [ka]

[0273] (In the formula, A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 and Q is defined as in formula (I), m is 1 or 2, preferably 1; and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0274] A given with respect to formula (I) 1, R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , and the preferred, more preferred, even more preferred and most preferred definitions of Q apply mutatis mutandis.

[0275] The present invention also relates to a compound of formula (7):

[0276] [ka]

[0277] (In the formula, A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, and R 7 is defined as in formula (I), m is 1 or 2, preferably 1; and X is halogen, preferably fluoro, chloro, or bromo.

[0278] A given with respect to formula (I) 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, and R 7 The definitions of preferred, more preferred, even more preferred and most preferred apply mutatis mutandis.

[0279] The present invention also provides a compound represented by formula (10) and formula (12):

[0280] [ka]

[0281] (In the formula, (In the formula, A 1 , R 3 , R 4 , R 5, L, R 6 , ring Y, p, R 7 and Q is defined as in formula (I), m is 1 or 2, preferably 1; E 1 is hydroxyl or halogen, preferably hydroxyl, chloro, or bromo; E 2 is hydroxyl or amino, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0282] A given with respect to formula (I) 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, R 7 , and the preferred, more preferred, even more preferred and most preferred definitions of Q apply mutatis mutandis.

[0283] The present invention also provides a compound represented by formula (14) and formula (15):

[0284] [ka]

[0285] (In the formula, A 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, and R 7 is defined as in formula (I), m is 1 or 2; X is halogen, preferably fluoro, chloro, or bromo; E 1 is hydroxyl or halogen, preferably hydroxyl, chloro, or bromo; E 2 is hydroxyl, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

[0286] A given with respect to formula (I) 1 , R 3 , R 4 , R 5 , L, R 6 , ring Y, p, and R 7 The definitions of preferred, more preferred, even more preferred and most preferred apply mutatis mutandis.

[0287] Compositions and Formulations The present invention further relates to compositions, in particular compositions for controlling unwanted microorganisms, which can be applied to the microorganisms and / or their habitat.

[0288] The compositions comprise at least one compound of formula (I) and at least one agriculturally suitable adjuvant, such as a carrier and / or surfactant.

[0289] Carriers are generally inert, solid or liquid, natural or synthetic, organic or inorganic. Carriers generally improve the application of compounds to plants, plant parts, or seeds, for example. Examples of suitable solid carriers include, but are not limited to, ammonium salts, especially ammonium sulfate, ammonium phosphate, and ammonium nitrate; natural rock powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth; silica gels and synthetic rock powders such as finely divided silica, alumina, and silicates. Examples of typically useful solid carriers for preparing granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, and dolomite; synthetic granules of inorganic and organic flours; and granules of organic materials such as paper, sawdust, coconut shells, corn cobs, and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include, for example, polar and non-polar organic chemical liquids from the class of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylenes, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene, or methylene chloride), alcohols and polyols (such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, or glycols, which may be optionally substituted, etherified, and / or esterified), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide or fatty acid amides) and their esters, lactams (such as N-alkylpyrrolidones, in particular N-methylpyrrolidone) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide), oils of vegetable or animal origin. The carrier may also be a liquefied gas extender, i.e., a liquid that is a gas at standard temperature and pressure, e.g., an aerosol propellant such as halohydrocarbons, butane, propane, nitrogen, carbon dioxide, etc.

[0290] Preferred solid supports are selected from clay, talc, and silica.

[0291] Preferred liquid carriers are selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams, and carbonate esters.

[0292] The amount of carrier will typically range from 1 to 99.99%, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, and most preferably from 20 to 99% by weight of the composition.

[0293] The liquid carrier will typically be present in the range 20 to 90% by weight of the composition, for example 30 to 80% by weight.

[0294] The solid carrier will typically be present in the range 0 to 50% by weight of the composition, preferably 5 to 45% by weight, for example 10 to 30% by weight.

[0295] If the composition includes two or more carriers, the ranges outlined refer to the total amount of carriers.

[0296] The surfactant may be an ionic (cationic or anionic), amphoteric or nonionic surfactant, such as an ionic or nonionic emulsifier, foaming agent, dispersant, wetting agent, penetration enhancer, and any mixture thereof. Examples of suitable surfactants include salts of polyacrylic acid, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid or naphthalenesulfonic acid, 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 ethoxylate, polyoxyethylene fatty alcohol ethers, e.g., alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols) and their ethoxylates (e.g., tristyrylphenols, tristyryl ... Examples of suitable salts include, but are not limited to, ethoxylates, salts of sulfosuccinates, taurine derivatives (preferably alkyl taurates), phosphate esters of polyethoxylated alcohols or phenols, fatty esters of polyols (such as fatty acid esters of glycerol, sorbitol, or sucrose), sulfates (such as alkyl sulfates and alkyl ether sulfates), sulfonates (e.g., alkyl sulfonates, aryl sulfonates, and alkyl benzene sulfonates), phosphate esters, protein hydrolysates, lignosulfite waste liquor, and methylcellulose. References to salts in this paragraph preferably refer to the respective alkali, alkaline earth, and ammonium salts.

[0297] Preferred surfactants are selected from polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, alkylbenzene sulfonates such as calcium dodecylbenzene sulfonate, castor oil ethoxylates, sodium lignosulfonates, and arylphenol ethoxylates such as tristyrylphenol ethoxylate.

[0298] The amount of surfactant will typically be in the range 5 to 40%, for example 10 to 20% by weight of the composition.

[0299] Further examples of suitable auxiliaries include water repellents, desiccants, binders (adhesives, tackifiers, fixatives such as carboxymethylcellulose, natural and synthetic polymers in powder, granule or latex form such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural and synthetic phospholipids such as cephalin and lecithin, polyvinylpyrrolidone, and tylose), thickeners and secondary thickeners (cellulose ethers, acrylic acid derivatives, xanthan gum, modified clays, such as products available under the name BENTONE®, and finely divided silica), stabilizers (such as low-temperature stabilizers, preservatives such as dichlorophene and benzyl alcohol), and the like. and hydroxybenzoates, ...

[0300] The choice of auxiliary agent depends on the intended application mode of the compound of formula (I) and / or the physical properties of the compound.In addition, auxiliary agent can be selected to impart specific properties (technical, physical, and / or biological properties) to the composition or the use form prepared therefrom.By selecting auxiliary agent, the composition can be customized to meet specific needs.

[0301] The compositions of the present invention may be provided to the end user as ready-to-use formulations, i.e., they may be applied directly to plants or seeds by suitable equipment, such as spray or dusting equipment. Alternatively, they may be provided to the end user in the form of a concentrate that must be diluted, preferably with water, before use.

[0302] The compositions of the present invention may be prepared in conventional manner, for example by mixing a compound of formula (I) with one or more suitable auxiliaries as disclosed above.

[0303] The composition contains a fungicidally effective amount of a compound of formula (I). The term "effective amount" refers to an amount sufficient to control harmful fungi in cultivated plants or to protect the material without causing substantial damage to the treated plants. Such amounts can vary widely and depend on various factors, such as the fungal species to be controlled, the cultivated plants or materials to be treated, climatic conditions, and the particular compound of formula (I) used. Typically, compositions according to the present invention contain 0.01 to 99% by weight, preferably 0.05 to 98% by weight, more preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight, and most preferably 1 to 80% by weight of a compound of formula (I). It is possible for a composition to contain more than one compound of the present invention. In such cases, the ranges outlined refer to the total amount of compounds of the present invention.

[0304] The compositions of the present invention may be in any conventional composition type, such as solutions (e.g., aqueous solutions), emulsions, aqueous and oily suspensions, dusts (e.g., wettable powders, soluble powders), dusts, pastes, granules (e.g., soluble granules, dusting granules), suspoemulsion concentrates, natural or synthetic products impregnated with a compound of formula (I), fertilizers, and microencapsulated polymeric materials. The compound of formula (I) may be present in suspended, emulsified, or dissolved form. Examples of specific suitable composition types include solutions, water-soluble concentrates (e.g., SL, LS), dispersible concentrates (DC), suspensions and suspension concentrates (e.g., SC, OD, OF, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME, SE), capsules (e.g., CS, ZC), pastes, lozenges, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), presses (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations for treating plant propagation materials such as seeds (e.g., GW, GF). These and further composition types are defined by the Food and Agriculture Organization of the United Nations (FAO). A summary is provided in "Catalogue of Pesticide Formulation Types and International Coding System" (Technical Monograph No. 2, 6th Ed. May 2008, Croplife International).

[0305] 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.

[0306] Examples of composition types and further details about their preparation are provided below. When two or more compounds of the present invention are present, the approximate amount of compounds of the present invention refers to the total amount of compounds of the present invention. This also applies mutatis mutandis to any further components of the composition, for example, wetting agents or binders, when there are two or more representatives of such components.

[0307] i) Water-soluble concentrates (SL, LS) 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 added to such an amount of water and / or a water-soluble solvent (e.g., a carbonate such as propylene glycol or propylene carbonate) that the total amount is 100% by weight. Before application, the concentrate is diluted with water.

[0308] ii) Dispersible Concentrate (DC) 5-25% by weight of at least one compound of formula (I) and 1-10% by weight of a surfactant and / or binder (e.g., polyvinylpyrrolidone) are dissolved in an amount of organic solvent (e.g., cyclohexanone) such that the total amount is 100% by weight. Upon dilution with water, a dispersion is obtained.

[0309] iii) Emulsifiable concentrate (EC) 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 combined with a water-insoluble organic solvent (e.g., an aromatic hydrocarbon or a fatty acid amide), and optionally an additional water-soluble solvent, to give a total of 100% by weight. Upon dilution with water, an emulsion is obtained.

[0310] iv) Emulsions (EW, EO, ES) 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). This mixture is added to the same amount of water using an emulsifier to make the total amount 100% by weight. The resulting composition is a homogeneous emulsion. This emulsion may be further diluted with water before application.

[0311] v) Suspensions and suspension concentrates v-1) Aqueous (SC, FS) For example, in a suitable grinding device, such as an agitator ball mill, 20-60% by weight of at least one compound of formula (I) is ground with 2-10% by weight of a surfactant (e.g., sodium lignosulfonate 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 such that the total amount becomes 100% by weight. Upon dilution with water, a stable suspension of the active substance is obtained. For FS-type compositions, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0312] v-2) Oil-based (OD, OF) For example, in a suitable grinding device, such as an agitator ball mill, 20-60% by weight of at least one compound of formula (I) is ground with 2-10% by weight of a surfactant (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether), 0.1-2% by weight of a thickener (e.g., modified clay, especially BENTONE® or silica), and an organic carrier to obtain a fine oily suspension of the active substance. The organic carrier is added in an amount such that the total amount is 100% by weight. Dilution with water results in a stable dispersion of the active substance.

[0313] vi) Water-dispersible granules and water-soluble granules (WG, SG) 50-80% by weight of at least one compound of formula (I) is pulverized with the addition of surfactants (e.g., sodium lignosulfonate and polyoxyethylene fatty alcohol ether) and converted into water-dispersible or water-soluble granules in technical equipment (e.g., extruders, spray towers, fluidized beds). The surfactants are used in an amount such that the total amount is 100% by weight. Dilution with water results in a stable dispersion or solution of the active substance.

[0314] vii) Water-dispersible and water-soluble powders (WP, SP, WS) 50-80% by weight of at least one compound of formula (I) is mixed with 1-8% by weight of a surfactant (e.g., sodium lignosulfonate, polyoxyethylene fatty alcohol ether) and a solid carrier, such as silica gel, and ground in a rotor-stator mill to a total of 100% by weight. Upon dilution with water, a stable dispersion or solution of the active substance is obtained.

[0315] viii) Gel (GW, GF) In an agitator ball mill, 5-25% by weight of at least one compound of formula (I) is ground with 3-10% by weight of a surfactant (e.g., sodium lignosulfonate), and 1-5% by weight of a binder (e.g., carboxymethylcellulose) and an amount of water to bring the total to 100% by weight. This results in a fine suspension of the active substance. Dilution with water results in a stable suspension of the active substance.

[0316] ix) Microemulsion (ME) 5-20% by weight of at least one compound of formula (I) is added to 5-30% by weight of an organic solvent blend (e.g., fatty acid dimethylamide and cyclohexanone), 10-25% by weight of a surfactant blend (e.g., polyoxyethylene fatty alcohol ether and arylphenol ethoxylate), and an amount of water such that the total amount is 100% by weight. The mixture is stirred for 1 hour to spontaneously form a thermodynamically stable microemulsion.

[0317] x) Microcapsules (CS) 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., aromatic hydrocarbon), and 2-15% by weight of an acrylic monomer (e.g., methyl methacrylate, methacrylic acid, di- or tri-acrylate) are dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Poly(meth)acrylate microcapsules are formed by radical polymerization initiated by a radical initiator. 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., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) are dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). The addition of a polyamine (e.g., hexamethylenediamine) results in the formation of polyurea microcapsules. This monomer accounts for 1-10% by weight of the total CS composition.

[0318] xi) Powder formulations (DP, DS) 1 to 10% by weight of at least one compound of formula (I) is finely ground and intimately mixed with such an amount of solid carrier, for example finely divided kaolin, that the total amount is 100% by weight.

[0319] xii) Granules (GR, FG) 0.5 to 30% by weight of at least one compound of formula (I) is finely ground and combined with an amount of a solid carrier (e.g., a silicate) to make up 100% by weight of the total. Granulation is accomplished by extrusion, spray drying, or fluidized bed.

[0320] xiii) Ultra-trace liquid (UL) 1-50% by weight of at least one compound of formula (I) is dissolved in such an amount of organic solvent, such as an aromatic hydrocarbon, that the total amount is 100% by weight.

[0321] The compositions of types i) to xiii) may optionally contain 0.1 to 1% by weight of an adjuvant such as a preservative, 0.1 to 1% by weight of an antifoaming agent, 0.1 to 1% by weight of a dye and / or pigment, and 5 to 10% by weight of an antifreeze.

[0322] Mixtures / Combinations The compounds of formula (I) and 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, semiochemicals, and / or other agriculturally beneficial agents are also possible. This can broaden the spectrum of activity and prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides, and bactericides are disclosed in the "Pesticide Manual" (17th Edition).

[0323] Examples of fungicides which may be mixed with the compounds of formula (I) and compositions of the present invention are: 1) Ergosterol biosynthesis inhibitors, for example: (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017 ) Propiconazole, (1.018) Prothioconazole, (1.019) Pyrisoxazole, (1.020) Spiroxamine, (1.021) Tebuconazole, (1.022) Tetraconazole, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2, 4-triazol-1-ylmethyl)cyclopentanol, (1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl) )phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031)(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) (1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,. 2,4-Triazol-5-yl thiocyanate, (1.040) 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}-1 H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]- 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-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2, 6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[ (2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1, 2,4-Triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)furan phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) Mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)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-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5- (Allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2, 4-Triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1. 065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N'-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N'-(2,5-dimethyl N-ethyl-N-methylimidoformamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2, 2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N'-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N'-(4-{[3-(difluoromethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide amide, (1.075)N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076)N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077)N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide )ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078)N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079)N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (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-triazol-1-yl)propyl]- (1.088) N'-{5-bromo-2-methyl-6-[(1-propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.089) hexaconazole, (1.090) penconazole, (1.091) fenbuconazole, (1.092) methyl-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, (1.093) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid.

[0324] 2) Inhibitors of the complex I or II respiratory chain, 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) isofetamide, (2.010) isopyrazam (anti-epimer enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimer enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimer racemic 1RS,4SR,9SR), (2.013) Isopyrazam (mixture of syn-epimer racemic 1RS,4SR,9RS and anti-epimer racemic 1RS,4SR,9SR), (2.014) Isopyrazam (syn-epimer enantiomer 1R,4S,9R), (2.015) Isopyrazam (syn-epimer enantiomer 1S,4R,9S), (2.016) Isopyrazam (syn-epimer racemic 1RS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019 ) Pydiflumetofen, (2.020) Pyraziflumide, (2.021) Sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1 H-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) Inpirfluxam, (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-indene-4-. N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-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-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide t-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) isoflucipram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1, 2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, ( 2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole- 4-Carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (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) (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide )-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide , (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) Pyrapropoin, (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.

[0325] 3) Inhibitors of the complex III respiratory chain, for example (3.001) ametoctrazine, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) methoxystrobin, (3.005) comoxystrobin, (3.006) cyazofamide, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresox. Symmethyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametstrobin, (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-methyl Acetamide, (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) fenpicoxamide, (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) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) methyltetraprole, (3.031) flurylpicoxamide.

[0326] 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) pyridaclomethyl, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridine-3- (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.

[0327] 5) Compounds capable of multi-site action, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(II) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) mancozeb Neb, (5.015) metiram, (5.016) metiram zinc, (5.017) oxine-copper, (5.018) propineb, (5.019) sulfur preparations containing sulfur and 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.

[0328] 6) Compounds capable of inducing host defense, such as (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

[0329] 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.

[0330] 8) Inhibitors of ATP production, for example (8.001) silthiofam.

[0331] 9) Inhibitors of cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamide, (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.

[0332] 10) Inhibitors of lipid and membrane synthesis, for example, (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos methyl.

[0333] 11) Inhibitors of melanin biosynthesis, for example, (11.001) tricyclazole, (11.002) tolprocarb.

[0334] 12) Inhibitors of nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M (chiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0335] 13) Inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.

[0336] 14) Compounds capable of acting as uncouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.

[0337] 15) (15.001) Abscisic acid, (15.002) Benthazole, (15.003) Bethoxadin, (15.004) Capsimycin, (15.005) Carvone, (15.006) Chinomethionate, (15.007) Kufuraneb, (15.008) Cyflufenamid (15.009) 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) Metrafenone, (15.017) Mildiomycin, (15.018) Natamycin, (15.019) Nickel dimethyldithiocarbamate, (15.020) Nitrotar isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapiproline, (15.023) Oxyfenthiin, (15.024) Pentachlorophenol and salts, (15.025) Phosphorous acid and its salts, (15.026) Propamocarb fosetylate -fosetylate), (15.027) pyriophenone (clazafenone), (15.028) tebufloquine, (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}piperidine-1- (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) dipimethitrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4 -{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4- (4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro- 1,2-Oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.041) Ipflufenoquin, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol ol, (15.043) fluoxapiproline, (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) quinofumeline, (15.048 ) 4-Amino-5-fluoropyrimidin-2-ol (tautomer: 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-sulfonohydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro- 2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.05 6) Ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057) Phenazine-1-carboxylic acid, (15.058) Propyl 3,4,5-trihydroxybenzoate, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfate (2:1), (15.061) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methyl]methyl}methyl ethylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.062) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063) aminopyrifen, (15.064) (N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide), ( 15.065) (N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide), (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 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-carbonimidoyl]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.084) N-[(Z)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol- 3-yl]benzamide, (15.085) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one oxadiazol-3-yl]benzenecarbothioamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide, (15.090) 1 -Methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091) 1,1-diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanediol amide, (15.093) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propanamide, (15.098) 1-methoxy-3-methyl-1-[[4-[ 5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.100) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101) 1-[[4-[5-(trifluoromethyl) (15.101) 4,4-dimethyl-2-[[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-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one, (15.106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.108) ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylate, (15.109) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazole-3-azone amine, (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.111) N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.113) 1-(5,6-dimethylpyridin-3-yl) )-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114) 1-(6-(difluoromethyl)-5-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}propanamide, (15.119) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4- Benzodioxepin-6-yl methanesulfonate, (15.120) 9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.121) 3-[2-(1-{[3,5-bis(difluoromethyl)- 1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.122) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate Dioxepin-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.

[0338] All named mixing partners of classes (1) to (15) above can be present in the form of free compounds or, if their functional groups allow this, in the form of their pesticidal active salts.

[0339] The compounds of formula (I) and compositions of the present invention may also be combined with one or more biological control agents.

[0340] As used herein, the term "biological control" is defined as the control of pests such as plant pathogenic fungi and / or insects and / or mites and / or nematodes through the use or employment of biological control agents.

[0341] As used herein, the term "biological control agent" is defined as an organism other than a harmful organism and / or a protein or secondary metabolite produced by such an organism for biological control. Mutants of a second organism are included in the definition of a biological control agent. The term "mutant" refers to variants of a parent strain, as well as methods for obtaining mutants or variants whose insecticidal activity is greater than that expressed by the parent strain. "Parent strain" is defined herein as the original strain prior to mutagenesis. To obtain such mutants, the parent strain may be thoroughly treated with chemicals such as N-methyl-N'-nitro-N-nitrosoguanidine, ethyl methanesulfone, or by irradiation using gamma, X-ray, or UV radiation, or by other means known to those skilled in the art. Known mechanisms of biological control include enterobacteria, which control root rot by outcompeting fungi for space on the root surface. Bacterial toxins, such as antibiotics, have been used to control pathogens. Toxins can be isolated and applied directly to plants, or bacterial species can be administered to produce the toxin in situ.

[0342] A "variant" is a strain that has all the identifying characteristics of the NRRL or ATCC accession number set forth in the specification and can be identified as having a genome that hybridizes under high stringency conditions to the genome of the NRRL or ATCC accession number.

[0343] "Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex stabilized through hydrogen bonding between the bases of nucleotide residues. Hydrogen bonding can occur through Watson-Crick base pairing, Hoogstein binding, or other sequence-specific methods. The complex can contain two strands forming a duplex structure, three or more strands forming a multi-stranded complex, a single self-hybridizing strand, or any combination thereof. Hybridization reactions can be performed under conditions of varying "stringency." Generally, low-stringency hybridization reactions are performed at about 40°C in 10xSSC or a solution of equivalent ionic strength / temperature. Moderate-stringency hybridization reactions are typically performed at about 50°C in 6xSSC, and high-stringency hybridization reactions are generally performed at about 60°C in 1xSSC.

[0344] A variant of a designated NRRL or ATCC accession number may also be defined as a strain having a genome sequence that has greater than 85%, more preferably greater than 90%, or more preferably greater than 95% sequence identity to the genome of the designated NRRL or ATCC accession number. A polynucleotide or polynucleotide region (or polypeptide or polypeptide region) having a certain percentage (e.g., 80%, 85%, 90%, or 95%) of "sequence identity" to another sequence means that, when aligned, a percentage of the bases (or amino acids) are identical when the two sequences are compared. This alignment and percent homology or sequence identity can be determined using software programs known in the art, such as those described in "Current Protocols in Molecular Biology" (F.M. Ausubel et al., eds., 1987).

[0345] "NRRL" is an abbreviation for "Agricultural Research Service Culture Collection," an international depository for the purpose of depositing microbial strains under the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure, and is located at the Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 North University Street, Pereira, Illinois, USA (Zip Code 61604).

[0346] "ATCC" is an abbreviation for "American Type Culture Collection," an international depository for the purpose of depositing microbial strains under the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure, and is located at 10801 University Boulevard, Manassas, Virginia, USA (Zip Code 10110).

[0347] Examples of biological control agents that can be combined with the compounds of formula (I) and compositions of the present invention are: (A) an antibacterial agent selected from the group consisting of: (A1) For example, the following bacteria: (A1.1) Bacillus subtilis, in particular the strain QST713 / AQ713 (available from Bayer CropScience, USA, as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661, U.S. Patent No. 6,060,051); (A1.2) Bacillus species, in particular the strain D747 (available from Kumiai Chemical Industry Co., Ltd., as DOUBLE NICKEL®), accession number FERM BP-8234, U.S. Patent No. 7,094,592; (A1.3) Bacillus pumilus, in particular BU strain F-33, NRRL accession number 50185 (available as part of BASF's CARTISSA® products, EPA registration number 71840-19); (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24, accession number DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)); (A1.5) Paenibacillus sp. strain, accession number NRRL B-50972 or accession number NRRL B- 67129, WO 2016 / 154297; (A1.6) Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA); (A1.7) Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (WO 2013 / 034938), Certis USA, a subsidiary of Mitsui & Co.; (A1.8) Bacillus subtilis CX-9060, Certis USA, a subsidiary of Mitsui & Co.; (A1.9) Paenibacillus polymyxa, in particular strain AC-1 (e.g., Green Biotech (A1.10) Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena); (A1.11) Pantoea agglomerans, in particular strain E325 (accession number NRRL B-21856) (available from Northwest Agri Products as BLOOMTIME BIOLOGICAL™ FD BIOPESTICIDE); and (A2) For example, the following fungi: (A2.1) Aureobasidium pullulans, in particular blastospores of the strain DSM 14940, of the strain DSM 14941, or a mixture of blastospores of the strains DSM 14940 and DSM 14941 (for example, BOTECTOR® and BLOSSOM PROTECT® from bio-ferm, Switzerland); (A2.2) Pseudozyma aphidis (disclosed in WO 2011 / 151819 by Yissum Research Development Company, Hebrew University of Jerusalem); (A2.3) certain species of Saccharomyces cerevisiae, Lesaffre et al., France; Compagnie CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938, or CNCM No. I-3939 (WO 2010 / 086790); (B) a biofungicide selected from the group consisting of: (B1) For example, the following bacteria: (B1.1) Bacillus subtilis, in particular the strain QST713 / AQ713 (available from Bayer CropScience, USA, as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661, and described in U.S. Pat. No. 6,060,051); (B1.2) Bacillus pumilus, in particular the strain QST2808 (available from Bayer CropScience, USA, as SONATA®, NRRL accession number B-30087, and described in U.S. Pat. No. 6,245,551); (B1.3) Bacillus pumilus, in particular the strain GB34 (available from Bayer, Germany, as Yield Shield®); (B1.4) Bacillus pumilus (B1.5) Bacillus amyloliquefaciens, particularly strain BU F-33, NRRL accession number 50185 (available from BASF as CARTISSA product, EPA registration number 71840-19); (B1.6) Bacillus subtilis Y1336 (available from BioNTech, Taiwan as BIOBAC® WP, registered in Taiwan as a biofungicide with registration numbers 4764, 5454, 5096, and 5277); (B1.7) Bacillus subtilis MBI 600 strain (available as SUBTILEX from BASF SE, accession number NRRL B-50595, U.S. Patent No. 5,061,495); (B1.8) Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, Germany); (B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24, accession number DSM 10271 (available as TAEGRO® or TAEGRO® ECO from Novozymes (EPA registration number 70127-5)); (B1.10) Bacillus mycoides J isolate, accession number B-30890 (available as BMJ from Certis USA, a subsidiary of Mitsui & Co., Ltd.) (B1.11) Bacillus licheniformis, in particular strain SB3086, accession number ATCC 55406, WO 2003 / 000051 (available from Certis USA, a subsidiary of Mitsui & Co., Ltd., as ECOGUARD® Biofungicide and GREEN RELEAF®); (B1.12) Paenibacillus species strains, accession number NRRL B-50972 or accession number NRRL B-67129, WO 2016 / 154297; (B1.13) Bacillus subtilis strain BU1814 (BASF available from Certis USA, Inc. as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA; (B1.14) Bacillus subtilis CX-9060, a Mitsui & Co. subsidiary, Certis USA; (B1.15) Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL accession number B-50768, WO 2014 / 028521) (STARGUS®, Marrone Bio Innovations); (B1.16) Bacillus amyloliquefaciens FZB42, accession number DSM 23117 (available as RHIZOVITAL® from ABiTEP GmbH, Germany); (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis. subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® from FMC Corporation); (B1.18) Bacillus mojavensis strain R3B (accession number NCAIM(P)B001389) (WO 2013 / 034938), Certis USA, a subsidiary of Mitsui & Co.; (B1.19) Paenibacillus polymyxa ssp. plantarum (WO 2016 / 020371), from BASF SE; (B1.20) Paenibacillus epiphyticus (WO 2016 / 020371), from BASF (B.1.21) Pseudomonas chlororaphis strain AFS009, accession number NRRL B-50897, WO 2017 / 019448 (e.g., HOWLER™ and ZIO™ from AgBiome Innovations, USA); (B1.22) Pseudomonas chlororaphis, in particular strain MA342 (e.g., CEDOMON™, CERALL™, and CEDRESS™ from Bioagri and Koppert); (B1.23) Streptomyces lydicus strain WYEC108 (Streptomyces lydicus (B1.24) Agrobacterium radiobacter strain K84 (e.g., GALLTROL-A® from AgBioChem, Canada); (B1.25) Agrobacterium radiobacter strain K1026 (e.g., NOGALL™ from BASF SE). (B1.26) Bacillus subtilis strain KTSB (FOLIACTIVE® from Donaghys); (B1.27) Bacillus subtilis IAB / BS03 (AVIV® from STK Bio-Ag Technologies); (B1.28) Bacillus subtilis strain Y1336 (available as BIOBAC® WP from BioN-Tech, Taiwan, registered in Taiwan as a biofungicide with registration numbers 4764, 5454, 5096, and 5277); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g., AVOGREEN® from the University of Pretoria); (B1.30) Bacillus methylotrophicus (B1.31) Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena); (B1.32) Streptomyces griseoviridis K61 (also known as Streptomyces galbus K61) (accession number DSM 7206) (MYCOSTOP® from Verdera); PREFENCE® from BioWorks, see Crop Protection 2006, 25, 468-475); (B1.33) Pseudomonas fluorescens A506 strain (e.g., BLIGHTBAN® from NuFarm); and (B2) Fungi, such as: (B2.1) Coniothyrium minitans, in particular the strain CON / M / 91-8 (accession number DSM-9660, e.g., Contans® from Bayer CropScience Biologics GmbH); (B2.2) Metschnikowia fructicola, in particular the strain NRRL Y-30752; (B2.3) Microsphaeropsis ochracea; (B2.5) Trichoderma atroviride, in particular the strain SC1 (accession number CBS 122089, WO 2009 / 116106 and U.S. Pat. No. 8,431,120 (Bi-PA)), strain 77B (Andermatt (B2.6) Trichoderma harzianum T-22 strain (e.g., Trianum-P from Andermatt Biocontrol or Koppert) or Cepa Simb-T5 strain (Simbiose Agro); (B2.14) Gliocladium roseum (also known as Clonostachys rosea f. rosea), in particular strain 321U from Adjuvants Plus, strain ACM941 as disclosed by Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root tot complex of field pea, Can Jour Plant Sci 83(3): 519-524), or strain IK726 (Jensen DF, et al. Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain 'IK726'; Australas Plant Pathol. 2007;36:95-101; (B2.35) Talaromyces flavus strain V117b; (B2.36) Trichoderma viride, 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, accession number FERM P-16510 (e.g., ECO-HOPE® from Kumiai Chemical Industry), strain T34 (e.g., T34 Biocontrol from Biocontrol Technologies, Spain), or strain ICC 012 from Isagro; (B2.38) Trichoderma atroviride atroviride) CNCM I-1237 strain (e.g., Esquive® WP from Agrauxine, France); (B2.39) Trichoderma atroviride strain number V08 / 002387; (B2.40) Trichoderma atroviride NMI strain V08 / 002388; (B2.41) Trichoderma atroviride NMI strain V0. 8 / 002389; (B2.42) Trichoderma atroviride NMI strain V08 / 002390; (B2.43) Trichoderma atroviride LC52 strain (e.g., Tenet from Agrimm Technologies); (B2.44) Trichoderma atroviride ATCC strain 20476 (IMI 206040); (B2.45) Trichoderma atroviride T11 strain (IMI352941 / CECT20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g., Trichodex® from Makhteshim, USA); (B2.49) Trichoderma asperellum, in particular the kd strain (e.g., T-Gro from Andermatt Biocontrol); (B2.50) Trichoderma harzianum ITEM908 strain (e.g., Trianum-P from Koppert); (B2.51) Trichoderma harzianum TH35 strain (e.g., Root-Pro from Mycontrol); (B2.52) Trichoderma virens (Gliocladium virens) virens), in particular the strain GL-21 (for example SoilGard from Certis, USA); (B2.53) Trichoderma viride strain TV1 (for example Trianum-P from Koppert); (B2.54) Ampelomyces quisqualis, in particular the strain AQ 10 (for example AQ 10® from IntrachemBio, Italy); (B2.56) Aureobasidium pullulans, specifically, blastospores of strain DSM14940; (B2. 57) Aureobasidium pullulans, in particular blastospores of the strain DSM 14941; (B2.58) Aureobasidium pullulans, in particular a mixture of blastospores of the strains DSM 14940 and DSM 14941 (e.g., Botector® from bio-ferm, Switzerland); (B2.64) Cladosporium cladosporioides strain H39, Accession number CBS122244, U.S. Patent Application Publication No. 2010 / 0291039 (according to Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g., Prestop® by Lallemand; (B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia strain KV01 (e.g., Vertalec® by Koppert / Arysta); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842), U.S. Pat. No. 7,579,183; (B2.75) Trichoderma atroviride strain SKT-1 (FERM P-16510), Japanese Patent Publication No. 11-253151(A); (B2.76) Trichoderma atroviride SKT-2 strain (FERM P-16511), Japanese Patent Publication No. 11-253151(A); (B2.77) Trichoderma atroviride SKT-3 strain (FERM P-17021), Japanese Patent Publication No. 11-253151(A); (B2.78) Trichoderma gamsii (formerly known as: (B2.79) Trichoderma harzianum strain DB 103 (available as T-GRO® 7456 by Dagutat Biolab); (B2.80) Trichoderma polysporum strain IMI 206039 (available as Binab TF WP by BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum, accession number Ts3550 (available as Tricovab by CEPLAC, Brazil); (B2.83) Ulocladium oudemansi oudemansii strain U3, accession number NM 99 / 06216 (e.g., BOTRY-ZEN® by Botry-Zen, New Zealand, and BOTRYSTOP® by BioWorks); (B2.84) Verticillium albo-atrum (formerly known as V. dahliae), strain WCS850, accession number WCS850, deposited at the Netherlands Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations); (B2.86) Verticillium chlamydosporium; (B2.87) a mixture of Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012), accession number CABI CC IMI 392716, and Trichoderma gamsii (formerly known as T. viride) species ICC 080, accession number IMI 392151 (e.g., BIO-TAM™ from Isagro USA and BIODERMA® from Agrobiosol de Mexico); (B2.88) Trichoderma asperelloides JM41R (accession number NRRL B-50759) (TRICHO from BASF SE) PLUS®; (B2.89) Aspergillus flavus strain NRRL 21882 (a product also known as AFLA-GUARD® from Syngenta / ChemChina); (B2.90) Chaetomium cupreum (Accession No. CABI 353812) (e.g., BIOKUPRUUM® by AgriLife); (B2.91) Saccharomyces cerevisiae, in particular the cell walls of the strain LASO2 (Agro-Levures et Derives), the strain LAS117 (CEREVISANE® by Lesaffre, ROMEO® by BASF SE), the strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938 and CNCM No. I-3939 by Lesaffre et Compagnie, France (WO 2010 / 086790); (B2.92) Trichoderma virens viren) strain G-41, formerly known as Gliocladium virens (accession number ATCC 20906) (e.g., ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP, BioWorks, USA); (B2.93) Trichoderma Trichoderma hamatum, accession number ATCC 28012; (B2.94) Ampelomyces quisqualis strain AQ10, accession number CNCM I-807 (e.g., AQ 10®, IntrachemBio, Italy); (B2.95) Phlebiopsis gigantea strain VRA 1992 (ROTSTOP®, Danstar Ferment); (B2.96) Penicillium steckii (DSM 27859, WO 2015 / 067800, BASF SE; (B2.97) Chaetomium globosum (known as RIVADIOM® by Rivale); (B2.98) Cryptococcus flavescens strain 3C (NRRL Y-50378); (B2.99) Dactylaria candida; (B2.100) Dilophosphora alopecuri (available as TWIST FUNGUS®); (B2.101) Fusarium oxysporum strain Fo47 (available as FUSACLEAN® by Natural Plant Protection); (B2.102) Pseudozyma flocculosa flocculosa strain PF-A22 UL (available under the trademark SPORODEX® from Plant Products, Canada); (B2.103) Trichoderma gamsii (formerly known as T. viride), strain ICC 080 (IMI CC 392151 CABI) (available under the trademark BIODERMA® from AGROBIOSOL DE MEXICO); (B2.104) Trichoderma fertile (e.g., TrichoPlus products from BASF); (B2.105) Muscodor roseus, in particular strain A3-5 (accession number NRRL 30548); (B2.106) Simplicillium lanosoniveum; Biological control agents with plant growth and / or plant health improving effects that can be combined in the compound combinations of the present invention, including: (C1) Bacteria selected from the group consisting of Bacillus pumilus, in particular the strain QST2808 (accession number: NRRL No. B-30087); Bacillus subtilis, in particular the strain QST713 / AQ713 (having NRRL accession number B-21661 and described in U.S. Patent No. 6,060,051, available from Bayer CropScience, USA, as SERENADE® OPTI or SERENADE®); Bacillus subtilis, in particular the strain AQ30002 (having NRRL accession number B-50421 and described in U.S. Patent Application Publication No. 13 / 330,576); Bacillus subtilis, in particular the strain AQ30004 (and NRRL B-50455, as described in U.S. Patent Application Publication No. 13 / 330,576); Sinorhizobium Sinorhizobium meliloti strain NRG-185-1 (NITRAGIN®, Bayer CropScience); Bacillus subtilis strain BU1814 (TEQUALIS®, BASF SE); Bacillus subtilis rm303 (RHIZOMAX®, Biofilm Crop Protection); Bacillus amyloliquefaciens pm414 (LOLI-PEPTA®, 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 BT013A (NRRL No. B-50924) (also known as Bacillus thuringiensis 4Q7), Bacillus cereus family member EE349 (NRRL No. B-50928), Bacillus amyloliquefaciens amyloliquefaciens SB3281 (ATCC No. PTA-7542, International Publication No. 2017 / 205258) Bacillus amyloliquefaciens TJ1000 (available as QUIKROOTS® from Novozymes); Bacillus firmus, in particular the strain CNMC I-1582 (e.g., VOTIVO® from BASF SE); Bacillus pumilus, in particular the strain GB34 (e.g., YIELD SHIELD® from Bayer Crop Science, Germany); Bacillus amyloliquefaciens, in particular the strain IN937a; Bacillus amyloliquefaciens, in particular the strain FZB42 (e.g., RHIZOVITAL® from ABiTEP, Germany); Bacillus amyloliquefaciens BS27 (accession number NRRL B-5015); a mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as QUARTZO® (WG) and PRESENCE®); Bacillus cereus, in particular the strain BP01 (ATCC 55675, e.g., MEPICHLOR® from Arysta Lifescience, USA); Bacillus subtilis, in particular the strain MBI 600 (e.g., SUBTILEX® from BASF SE); Bradyrhizobium japonicum (e.g., OPTIMIZE® from Novozymes); Mesorhizobium cicer (e.g., NODULATOR from BASF SE); Rhizobium leguminosarium biovar viciae (e.g., Rhizobium leguminosarium biovar viciae) (e.g., Rhizobium leguminosarium biovar viciae) (e.g., Rhizobium leguminosarium biovar viciae) NODULATOR; Delftia acidovorans, in particular the strain RAY209 (e.g., BIOBOOST® from Brett Young Seeds); Lactobacillus species (e.g., LACTOPLANT® from LactoPAFI); Paenibacillus polymyxa, in particular the strain AC-1 (e.g., TOPSEED® from Green Biotech Company); Pseudomonas proradix (e.g., PRORADIX® from Sourcon Padena); Azospirillum brasilense (e.g., VIGOR® from KALO); Azospirillum lipoferum (e.g., VERTEX-IF® from TerraMax); Azotobacter vinelandii a mixture of Pseudomonas aeruginosa, in particular the strain PN1; Rhizobium leguminosarum, in particular (biovar) bv. viceae strain Z25 (accession number CECT 4585); Azorhizobium caulinodans, Azotobacter chroococcum, in particular strain H23; Azotobacter vinelandii, 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 species (e.g., CROPAID® from Cropaid, UK); and (C2) Fungi selected from the group consisting of Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) strain 251 (AGAL 89 / 030550, e.g., BioAct from Bayer CropScience Biologics GmbH), Penicillium bilaii strain ATCC 22348 (e.g., JumpStart® from Acceleron BioAg), and Talaromyces flavus strain V117b; Trichoderma atroviride strain CNCM I-1237 (e.g., Esquive® WP from Agrauxine, France); Trichoderma viride viride, for example, strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); Trichoderma atroviride strain LC52 (also known as Trichoderma atroviride strain LU132, e.g., Sentinel from Agrimm Technologies); Trichoderma atroviride strain SC1, as described in International Application No. PCT / IT2008 / 000196. Trichoderma asperellum strain kd (e.g., T-Gro from Andermatt Biocontrol); Trichoderma asperellum strain Eco-T (Plant Health Products, South Africa); Trichoderma harzianum strain T-22 (e.g., Trianum-P from Andermatt Biocontrol or Koppert); Myrothecium verrucaria strain AARC-0255 (e.g., DiTera™ from Valent Biosciences); Penicillium bilaii strain ATCC ATCC20851; Pythium oligandrum strain M1 (ATCC 38472, e.g., Polyversum from Bioprepraty, Czech Republic; Trichoderma virens strain GL-21 (e.g., SoilGard® from Certis, USA); Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS 276).92, e.g., Dutch Trig from Tree Care Innovations; Trichoderma atroviride, in particular strain V08 / 002387, NMI number V08 / 002388, NMI number V08 / 002389, and NMI number V08 / 002390; Trichoderma harzianum strain ITEM 908; Trichoderma harzianum strain TSTh20; Trichoderma harzianum strain 1295-22; Pythium oligandrum strain DV74; Rhizopogon amylopogon (e.g., Helena Chemical Company's Myco-Sol); Rhizopogon fulvigleba (e.g., Helena Chemical Company's Myco-Sol); and Trichoderma virens strain GI-3. an insecticidally active biological control agent selected from: (D1) Bacteria selected from the group consisting of Bacillus thuringiensis subsp. aizawai, particularly strain ABTS-1857 (SD-1372, for example, XENTARI® from Valent BioSciences); Bacillus mycoides, J isolate (for example, BmJ from Certis USA, a subsidiary of Mitsui & Co.); Bacillus sphaericus, particularly serotype H5a5b, strain 2362 (ABTS-1743) (for example, VECTOLEX®, Valent BioSciences, USA; Bacillus thuringiensis subsp. kurstaki strain BMP 123, Becker Microbial Products, Israel; Bacillus thuringiensis subsp. aizawai, in particular serotype H-7 (e.g., FLORBAC®, Valent BioSciences, USA); Bacillus thuringiensis subsp. kurstaki strain HD-1 (e.g., DIPEL®, Valent BioSciences, USA); Bacillus thuringiensis subsp. kurstaki strain BMP 123, Becker Microbial Products, Israel Bacillus thuringiensis (subsp.) israelensis strain BMP 144 (e.g., AQUABAC® by Becker Microbial Products, Israel); Burkholderia species, in particular Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI305) (accession number NRRL B-50319, WO 2011 / 106491 and WO 2013 / 032693; e.g., MBI-206 TGAI and ZELTO® by Marrone Bio Innovations); Chromobacterium subtsugae subtsugae), in particular the PRAA4-1T strain (MBI-203, e.g., GRANDEVO® from Marrone Bio Innovations); Paenibacillus popilliae (formerly Bacillus popilliae), e.g., St. Gabriel Laboratories' MILKY SPORE POWDER™ and MILKY SPORE GRANULAR™; Bacillus Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (accession number ATCC 1276) (e.g., VECTOBAC®, Valent BioSciences, USA); Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., BIOPROTEC®, AEF Global); Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428, e.g., NOVODOR®, BioFa, Germany); Bacillus thuringiensis var. japonensis (Bacillus thuringiensis var. japonensis) strain Buibui; Bacillus thuringiensis subsp. kurstaki (ABTS 351); Bacillus thuringiensis subsp. kurstaki (PB 54); Bacillus thuringiensis subsp. kurstaki (SA 11); Bacillus thuringiensis subsp. kurstaki (SA 12); Bacillus thuringiensis subsp. kurstaki (EG 2348); Bacillus thuringiensis var. Colmeri) (e.g., TIANBAOBTC by Changzhou Jianghai Chemical Factory Co., Ltd.); Bacillus thuringiensis subsp.aizawai strain GC-91; Serratia entomophila (e.g., INVADE® from Wrightson Seeds); Serratia marcescens, in particular strain SRM (accession number MTCC 8708); and Wolbachia pipientis strain ZAP (e.g., ZAP MALES® from MosquitoMate); and (D2) A fungus selected from the group consisting of: Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) apopka 97 strain; Beauveria bassiana ATCC 74040 strain (e.g., NATURALIS® from Intrachem Bio, Italy); Beauveria bassiana GHA strain (accession number ATCC 74250, e.g., BOTANIGUARD® ES and MYCONTROL-O® from Laverlam International Corporation); Zooftora radicans; Metarhizium robertii Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073), Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075), and Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074) (WO 2017 / 066094, Pioneer Hi-Bred International); Beauveria bassiana strain ATP02 (accession number DSM 24665). Among these, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain apopka 97 is particularly preferred. (E) a virus selected from the group consisting of Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton budworm larvae) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (siberian armyworm larvae) mNPV, and Spodoptera littoralis (African cotton leafworm) NPV; (F) Bacteria and fungi that can be added as "inoculants" to plants or plant parts or plant organs and that, by their specific properties, promote plant growth and plant health. Examples include: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, buchneri, Paraglomus species, Pisolithus tinctorus, Pseudomonas species, Rhizobium species, in particular Rhizobium trifolii, Rhizopogon species, Scleroderma species, Suillus species, and Streptomyces species; and (G) Plant extracts and products formed by microorganisms containing proteins and secondary metabolites that can be used as biological control agents, e.g., 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 (pyrethrum / pyrethrin), Cassia amara, amara, Quercus, Quillaja, Regalia, "Requiem™ Insecticide", rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, TRIACT® 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extracts, in particular rapeseed powder or mustard powder, as well as bioinsecticidal and acaricidal active substances obtained from olive oil, in particular those having a carbon chain length of C as the active ingredient. 16 -C 20 Unsaturated fatty acids / carboxylic acids having the formula: such as those contained in products under the trade name FLiPPER®.

[0348] The compounds of formula (I) and compositions of the present invention may be combined with one or more active ingredients selected from insecticides, acaricides, and nematicides.

[0349] The terms "insecticide" and "insecticidal" refer to the ability of a substance to increase the mortality rate or inhibit the growth rate of insects. As used herein, the term "insects" includes all organisms of the class "Insecta."

[0350] "Nematicide" and "nematicidal" refer to the ability of a substance to increase mortality or inhibit the growth rate of nematodes. Generally, the term "nematodes" includes eggs, larvae, juveniles, and adult forms of the organisms.

[0351] "Acaricide" and "acaricidal" refer to the ability of a substance to increase mortality or inhibit the growth rate of ectoparasites of the class Arachnida, subclass Acarina.

[0352] Examples of insecticides, acaricides and nematicides that can be mixed with the compounds of formula (I) and compositions of the present invention are respectively: (1) Acetylcholinesterase (AChE) inhibitors, for example, carbamates, such as alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates, such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP ... tophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphr, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imithiaphos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton methyl, parathion methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion.

[0353] (2) GABA-gated chloride channel blockers, for example, cyclic diene organochlorine compounds such as chlordane and endosulfan, or phenylpyrazoles (fiproles) such as ethiprole and fipronil.

[0354] (3) Sodium channel modulators, for example, pyrethroids, for example, acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empent phosphate [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadesrin, momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer)], tralomethrin, and transfluthrin, or DDT, or methoxychlor, etc.

[0355] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, for example, neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone.

[0356] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, for example, spinosyns, such as spinetoram and spinosad.

[0357] (6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as avermectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin, and milbemectin.

[0358] (7) Juvenile hormone mimetics, for example, juvenile hormone analogs, such as hydroprene, kinoprene, and methoprene, or fenoxycarb, or pyriproxyfen.

[0359] (8) Other nonspecific (multi-site) inhibitors, such as alkyl halides, e.g., methyl bromide and other alkyl halides, or chloropicrin, or sulfuryl fluoride, or borax, or tartar emetic, or methyl isocyanate generators, e.g., diazomet and metam.

[0360] (9) Chordotonal organ modulators such as, for example, pymetrozine or flonicamide.

[0361] (10) Mite growth inhibitors such as, for example, clofentezine, hexythiazox, and diflobidazine, or etoxazole.

[0362] (11) Microbial-derived insect midgut membrane disrupting agents, such as Bacillus thuringiensis ssp. israelensis, Bacillus sphaericus, Bacillus thuringiensis ssp. aizawai, Bacillus thuringiensis ssp. kurstaki, and Bacillus thuringiensis ssp. tenebrionis. tenebrionis), and Bacillus thuringiensis plant proteins (Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1), etc.

[0363] (12) Mitochondrial ATP synthase inhibitors, for example, ATP disrupting agents such as diafenthiuron, or organotin compounds, for example, azocyclotin, cyhexatin, and fenbutatin oxide, or propargite, or tetradifon.

[0364] (13) Oxidative phosphorylation uncouplers, such as chlorfenapyr, DNOC, and sulfluramide, due to disruption of the proton gradient.

[0365] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocyclam, and thiosultap sodium salt.

[0366] (15) Chitin biosynthesis inhibitors, type 0, such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0367] (16) Chitin biosynthesis inhibitors, type 1, such as buprofezin.

[0368] (17) Molting disruptors (especially Diptera, i.e., Diptera), such as cyromazine.

[0369] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

[0370] (19) Octopamine receptor agonists, such as amitraz.

[0371] (20) Mitochondrial electron transport chain complex III inhibitors, such as hydramethylnon, acequinocyl, or fluacrypyrim.

[0372] (21) Mitochondrial electron transport chain complex I inhibitors, such as those from the group of METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, and tolfenpyrad, or rotenone (Derris).

[0373] (22) Voltage-gated sodium channel blockers, such as indoxacarb or metaflumizone.

[0374] (23) Acetyl-CoA carboxylase inhibitors, such as tetronic acid and tetramic acid derivatives, for example, spirodiclofen, spiromesifen, spirotetramat.

[0375] (24) Mitochondrial electron transport chain complex IV inhibitors, for example, phosphines, such as aluminum phosphide, calcium phosphide, phosphine, and zinc phosphide, or cyanides, such as calcium cyanide, potassium cyanide, and sodium cyanide.

[0376] (25) Mitochondrial electron transport chain complex II inhibitors, such as β-ketonitrile derivatives, cyenopyrafen and cyflumetofen, and carboxanilides, such as piflubumid.

[0377] (28) Ryanodine receptor modulators, for example, diamides, such as chlorantraniliprole, cyantraniliprole, and flubendiamide; Further active compounds, such as Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionate, Chloroprallethrin, Ice Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dichloromezotiaz, Dicofol, ε-Metofluthrin, ε-Momfluthrin, Flometoquin, Fluazaindolizine, (Fluensulfone), Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiazol, Iprodione ione), κ-bifenthrin, κ-tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirodiclofen, Tetramethylfluthrin,Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen, Thiofluoximate, , Triflumezopyrim, and further preparations based on iodomethane, Bacillus firmus (I-1582, BioNeem, Votivo), as well as 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 WO 2006 / 043635) (CAS number 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO 2003 / 106457) 2006 / 003494) (CAS number 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 number 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2- Oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (known from EP 2647626) (CAS number 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160) (CAS number 792914-58-0), PF1364 (known from JP 2010 / 018586 A) (CAS number 1204776- 60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO 2012 / 029672) (CAS number 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from WO 2013 / 144213) (CAS number 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO 2010 / 051926) (CAS number 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from China Patent Application Publication No. 103232431) (CAS number 1449220-44-3), 4-[ 5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide, and (-)-N-[3-chloro-1-( 3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide (known from WO 2013 / 162715(A2), WO 2013 / 162716(A2), and U.S. Patent Application Publication No. 2014 / 0213448(A1)) (CAS number 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-.Pyrazole-3-carbonitrile (known from Chinese Patent Application Publication No. 101337937(A)) (CAS No. 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from Chinese Patent Application Publication No. 103109816(A)) (CAS No. 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 number 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5- Carboxamide (known from WO 2011 / 085575(A1)) (CAS number 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 Chinese Patent Application Publication No. 101337940(A)) (CAS number 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3- (Trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (known from Chinese Patent Application Publication No. 101715774(A)) (CAS No. 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylic acid ester (known from Chinese Patent Application Publication No. 103524422(A)) (CAS No. 1542271-46-4);(4aS)-7-Chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indene[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from Japanese Patent Application Publication No. 102391261(A)) (CAS No. 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 Patent Application Publication No. 2014 / 0275503(A1)) (CAS No. 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS No. 1253850-56-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-; 3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS number 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (known from WO 2007 / 040280(A1) and WO 2007040282(A1)) (CAS number 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]- N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide (known from WO 2015 / 058021(A1) and WO 2015 / 058028(A1)) (CAS number 1477919-27-9) and N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from Chinese Patent Application Publication No. 103265527(A)) (CAS number 1452877-50-7), 5-(1,3-dioxane-2- 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) and WO 2011 / 151146(A1)) (CAS number 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from WO 2013 / 115391(A1)) (CAS number 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) and WO 2011 / 151146(A1)) (CAS number 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 number 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-carboxylic acid ethyl ester (known from WO 2010 / 066780(A1) and WO 2011151146(A1)) (CAS number 1229023-00-0), N -[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from German Patent Application Publication No. 3639877(A1) and International Publication No. WO 2012029672(A1)) (CAS number 1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from International Publication No. WO 2016005276(A1)) (CAS number 1689566-03-7), [N (Z)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide, (CAS number 1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from WO 2011 / 105506(A1) and WO 2016 / 133011(A1)) (CAS number 1332838-17-1).

[0378] Examples of herbicides that can be mixed with the compounds of formula (I) and compositions of the present invention are: Acetochlor, acifluorfen, acifluorfen sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, Asulam, Atrazine, Azafenidine, Azimsulfuron, Beflubutamid, Benazolin, Benazolin-ethyl, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Benzuride, Bentazon, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Biranaphos, Biranaphos-sodium, Bispyribac, Bispyribac-sodium, Bixlozone, Bromacil, Bromobutide, Bromof phenoxime, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate, and -octanoate, busoxynone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butyrate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl- 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1,3-dimethyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, chlorfenac, chlorfenac sodium, chlorfenprop, chlor Flurenol, chlorflurenol methyl, chloridazon, chlorimuron, chlorimuron ethyl, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 4-{2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl}-1-ethyl-1H-pyrazol-5-yl-1,3-dimethyl-1H- Pyrazole-4-carboxylate, chlorophthalim, chlorotoluron, chlorthal-dimethyl, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clasifos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranyl, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butoxyl, -butyl, -dimethylammonium, -diol Amine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, daimuron / dymron, dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefron, dimepiperate, dimethachlor, dimethametrine, 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, diphenamide, diquat, diquat-dibromide, dithiopyr, diuron, DMPA, DNOC, endothall, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxybenzoate Fen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, ethyl-[(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, F-9960, F-5231, i.e., N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1yl]-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, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac , flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium, and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, Glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium, and -trimesium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropyl phosphoramidothioate, haloxifen, haloxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop- Methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidinone quinazolin-2-one, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxide-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, potassium, and sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-Oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium, and -sodium, MCPB, MCPB-methyl, -ethyl, and -sodium, mecoprop, mecoprop-sodium and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium ammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozoline, 2-({2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)pyridine-3- yl}carbonyl)cyclohexane-1,3-dione, methyl isothiocyanate, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-ylpropane-1-sulfonate, metobromuron, metolachlor, S-metolachlor, metosulam, Metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e., N-[3-chloro-4-isopropylphenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)- ) Methanone, nebron, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petroleum, phenmedipham,Picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufe Pyraflufen-ethyl, pyrasulfotole, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxifen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium , pyroxasulfone, piroxsulam, 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, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron , SYN-523, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid), TCA sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, tetflupyrrolimet, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, trisulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, 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.

[0379] Examples of plant growth regulators are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac sodium, endothal, endothal dipotassium, disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole 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-alanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0380] Examples of safeners that may be mixed with the compounds of formula (I) and compositions of the present invention include benoxacor, cloquintocet(-methyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole(-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen(-ethyl), mefenpyr(-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS No. 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS No. 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS No. 52836-31-4).

[0381] Examples of nitrification inhibitors that can be mixed with the compounds of formula (I) and 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-dimethylpyrazolium glycolate, 3,4-dimethylpyrazolium citrate, 3,4-dimethylpyrazolium lactate, 3,4-dimethylpyrazolium 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, triazonyl-formaldehyde-dicyandiamide adduct, 2-cyano-1-((4-oxo-1,3,5-triazinan-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-linoleic acid, methyl p-coumarate, methyl ferulate, methyl 3-(4-hydroxyphenyl)propionate, karanjin, brachialactone, p-Benzoquinone sorgoleone, 4-amino-1,2,4-triazole hydrochloride, 1-amido-2-thiourea, 2-amino-4-chloro-6-methylpyrimidine, 2-mercapto-benzothiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiodiazole (telazol, etridiazole), 2-sulfanilamidothiazole, 3-methylpyrazole, 1,2,4-triazolethiourea, cyanamide, melamine, zeolite powder, catechol, benzoquinone, sodium tetraborate, allylthiourea, chlorate, and zinc sulfate.

[0382] The compounds of formula (I) and compositions of the present invention may be combined with one or more agriculturally beneficial agents.

[0383] Examples of agriculturally beneficial agents include biostimulants, plant growth regulators, plant signaling molecules, growth promoters, microbial stimulating molecules, biomolecules, soil amendments, nutrients, plant nutritional enhancers, such as lipochitooligosaccharides (LCO), chitooligosaccharides (CO), chitin compounds, flavonoids, jasmonic acid or its derivatives (e.g., jasmonic acid), cytokinins, auxins, gibberellins, abscisic acid, ethylene, brassinosteroids, salicylates, macro- and micronutrients, linoleic acid or its derivatives, karrikins, beneficial microorganisms (e.g., Rhizobium sp., Bradyrhizobium sp., Sinorhizobium sp., Azorhizobium sp., Glomus sp., Gigasp ora) species, Hymenoscyphous species, Oidiodendron species, Laccaria species, Pisolithus species, Rhizopogon species, Scleroderma species (Scleroderma) species, Rhizoctonia species, Acinetobacter species, Arthrobacter species, Arthrobotrys species, Aspergillus species (A spergillus sp., Azospirillum sp., Bacillus sp., Burkholderia sp., Candida sp., Chryseomonas sp., Enterobacter sp. Enterobacter sp., Eupenicillium sp., Exiguobacterium sp., Klebsiella sp., Kluyvera sp., Microbacterium sp. icrobacterium species, Mucor species, Paecilomyces species, Paenibacillus species, Penicillium species, Pseudomonas species,Serratia spp., Stenotrophomonas spp., Streptomyces spp., Streptosporangium spp., Swaminathania spp., Thiobacillus spp., Torulospora spp., Vibrio spp., Xanthobacter spp., Xanthomonas spp., and the like, and combinations thereof.

[0384] Methods and Uses The compound of formula (I) and the composition of the present invention have strong fungicidal activity and / or plant defense regulation ability.They can be used to control unwanted microorganisms such as unwanted fungi and bacteria in plants.As will be described in more detail below, they can be particularly useful for crop protection (controlling microorganisms that cause plant diseases) or protecting materials (such as industrial materials, timber, and stored goods).More specifically, the compound of formula (I) and the composition of the present invention can be used to protect seeds, germinated seeds, germinating seedlings, plants, plant parts, fruits, harvested products, and / or the soil in which plants grow from unwanted microorganisms.

[0385] As used herein, "control" or "controlling" includes the protection, treatment, and eradication of undesirable microorganisms. Undesirable microorganisms may be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes, or pathogenic fungi, more specifically, plant pathogenic bacteria, plant pathogenic viruses, plant pathogenic oomycetes, or plant pathogenic fungi. As described in detail below, these plant pathogenic microorganisms are the causative agents of a wide range of plant diseases.

[0386] More specifically, the compounds of formula (I) and compositions of the present invention can be used as fungicides. For the purposes of this specification, the term "fungicide" refers to compounds or compositions that can be used in crop protection to control undesirable fungi such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes, and / or to protect against oomycetes.

[0387] The compounds of formula (I) and compositions of the present invention can also be used as antibacterial agents.In particular, they can be used in crop protection, such as controlling unwanted bacteria, for example, Pseudomonadaceae, Rhizobiaceae, Xanthomonadaceae, Enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae.

[0388] The compounds of formula (I) and the compositions of the present invention can also be used as antiviral agents in crop protection. For example, the compounds of formula (I) and the compositions of the present invention can be used to combat Tobacco Mosaic Virus (TMV), Tobacco Rattle Virus, Tobacco Dwarf Virus (TStuV), Tobacco Leaf Curl Virus (VLCV), Tobacco Nervilia Mosaic Virus (TVBMV), Tobacco Necrotic Dwarf Virus (TNDV), Tobacco Streak Virus (TSV), Potato Virus X (PVX), Potato Virus Y, S, M, and A, Potato Ocuba Mosaic Virus (PAMV), Potato Mop Top Virus (PMTV), Potato Leaf Roll Virus (PLRV), Alfalfa Mosaic Virus (AMV), Cucumber Mosaic Virus (Cucumber Mosaic Virus), Tobacco Spike Virus (TSV ... The virus may be effective against diseases caused by plant viruses such as Cucumber green mottle 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 stripe virus, Strawberry mottle virus (SMoV), Strawberry vein banding virus (SVBV), Strawberry mild yellow edge virus (SMYEV), Strawberry crinkle virus (SCrV), Broad bean wilt virus (BBWV), and Melon necrotic spot virus (MNSV).

[0389] The present invention also relates to a method for controlling undesirable microorganisms, such as undesirable fungi, oomycetes, and bacteria, on plants, comprising the step of applying at least one compound of formula (I) or at least one composition of the present invention to the microorganisms and / or their habitat (plants, plant parts, seeds, fruits, or the soil in which the plants grow).

[0390] Typically, when the compounds of formula (I) and compositions of the present invention are used in a curative or protective method to control phytopathogenic fungi and / or phytopathogenic oomycetes, an effective and plant-compatible amount is applied to plants, plant parts, fruits, seeds, or the soil or substrate on which the plants grow. Suitable substrates that can be used to cultivate plants include inorganic-based substrates such as mineral wool, especially stone wool, perlite, sand, or gravel; organic substrates such as peat, pine bark, and sawdust; and petroleum-based substrates such as polymer foam or plastic beads. A plant-compatible effective amount is an amount sufficient to control or destroy fungi that may be present or appear in agricultural soil without causing noticeable symptoms of phytotoxicity to the crop. Such amounts may vary within wide ranges depending on the fungi to be controlled, the type of crop, the stage of crop development, climatic conditions, and the respective compounds or compositions of the present invention used. This amount can be determined by systematic field testing, which is within the capabilities of those skilled in the art.

[0391] Plants and plant parts The compounds of formula (I) and compositions of the present invention may be applied to any plant or plant part.

[0392] Plants means all plants and plant populations, such as desirable and undesirable wild plants or crop plants (including naturally occurring crop plants). Crops are plants that can be obtained by conventional breeding and optimization methods, or by biotechnology and genetic engineering methods, or a combination of these methods, and include genetically modified plants (GMOs or transgenic plants), and plant varieties that can and cannot be protected by plant breeders' rights.

[0393] Plant varieties are understood to mean plants having new properties ("traits") and obtained by conventional breeding, mutagenesis or recombinant DNA techniques. They may be cultivars, varieties, biotypes or genotypes.

[0394] Plant parts are understood to mean all parts and organs of a plant, above and below ground, such as shoots, leaves, needles, stalks, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers, rhizomes, etc. Plant parts also include harvested material, plant material and reproductive propagation material, such as cuttings, tubers, rhizomes, slips and seeds.

[0395] Plants that can be treated according to the method of the present invention may include cotton, flax, grapes, fruits, vegetables, such as species of the Rosaceae family (including, for example, pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds, peaches, and soft fruits such as strawberries), species of the Ribesioidae family, species of the Juglandaceae family, species of the Birch family, species of the Anacardiaceae family, species of the Fagaceae family, species of the Moraceae family. species, Oleaceae species, Actinidaceae species, Lauraceae species, Musaceae species (e.g., banana trees and plantations), Rubiaceae species (e.g., coffee), Theaceae species, Sterculiceae species, Rutaceae species (e.g., lemons, oranges, and grapefruit); Solanaceae species (e.g., tomatoes), Liliaceae species, Asteraceae e) species (e.g. lettuce), Umbelliferae species, Cruciferae species, Chenopodiaceae species, Cucurbitaceae species (e.g. cucumber), Alliaceae species (e.g. leeks and onions), Papilionaceae species (e.g. peas); staple crops, e.g. Gramineae species (e.g. cereals such as maize, grass, wheat, rye, rice, barley, oats, millet, triticale), Asteraceae seeds (e.g. sunflower), Brassicaceae species (e.g. white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, bok choy, kohlrabi, radish, rapeseed, mustard, horseradish, watercress), Fabcae species (e.g. beans, peanuts), Papilionaceae species (e.g. soybean), Solanaceae species (e.g. potato), Chenopodiaceae species (e.g. sugar beet, fodder beet, Swiss chard, beetroot);Useful plants and ornamental plants for gardens and wooded areas; as well as genetically modified varieties of each of these plants.

[0396] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are tolerant to one or more biotic stresses, i.e., that exhibit better protection against animal and microbial pests such as nematodes, insects, mites, plant pathogens, bacteria, viruses and / or viroids.

[0397] Plants and plant varieties that can be treated by the methods disclosed above include plants that are tolerant to one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, exposure to low temperatures, exposure to heat, osmotic stress, flooding, increased soil salinity, increased exposure to minerals, exposure to ozone, exposure to strong light, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, and shade avoidance.

[0398] Plants and plant varieties that can be treated by the methods disclosed above include plants characterized by improved yield characteristics. Increased yield in such plants can be the result of improved plant physiology, growth, and development, such as improved water use efficiency, water retention efficiency, improved nitrogen utilization, improved carbon assimilation, improved photosynthesis, improved germination efficiency, and accelerated maturation. Furthermore, yield can be influenced by improved plant architecture (under stress and non-stress conditions), including, but not limited to, earlier flowering, controlled flowering for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, number of pods or panicles, number of seeds per pod or panicle, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Additional yield characteristics include seed composition, such as carbohydrate content and composition (e.g., cotton or starch), protein content, oil content and composition, nutritional value, reduced antinutritional compounds, improved processability, and better storage stability.

[0399] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are hybrid plants that already express characteristics of hybrid vigor or hybrid vigor that generally result in higher yield, vigor, health, and resistance to biotic and abiotic stresses.

[0400] Transgenic plants, seed treatments, and integration events The compounds of formula (I) can be advantageously used to treat transgenic plants, plant cultivars, or plant parts that have received genetic material that confers advantageous and / or useful properties (traits) to these plants, plant cultivars, or plant parts. It is therefore contemplated that the present invention can be combined with one or more recombinant traits, transgenic events, or combinations thereof. For purposes of this application, a transgenic event is created by the insertion of a specific recombinant DNA molecule into a specific location (locus) within a chromosome of the plant genome. The insertion creates a new DNA sequence, referred to as an "event," characterized by the inserted recombinant DNA molecule and some amount of genomic DNA immediately adjacent to / flanking both ends of the inserted DNA. Such traits or transgenic events include, but are not limited to, pest resistance, water use efficiency, yield performance, drought tolerance, seed quality, improved nutritional quality, hybrid seed production, and herbicide tolerance. The trait is measured relative to a plant lacking such trait or transgenic event. Specific examples of such advantageous and useful properties (traits) are better plant growth, vigor, stress tolerance, stability, lodging resistance, nutrient uptake, plant nutrition, and / or yield, in particular improved growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salinity levels, improved flowering performance, easier harvesting, accelerated ripening, increased yield, higher quality and / or nutritional value of the harvested product, improved storage life and / or processability of the harvested product, and increased resistance to animal and microbial pests such as insects, arachnids, nematodes, mites, slugs, snails, etc.

[0401] Among DNA sequences encoding proteins that confer resistance to such animal and microbial pests, especially insects, we particularly refer to genetic material from Bacillus thuringiensis that encodes Bt proteins, which are widely described in the literature and well known to those skilled in the art. We also refer to proteins extracted from bacteria such as Photorhabdus (WO 97 / 17432 and WO 98 / 08932). We particularly refer to Bt Cry proteins or VIP proteins. These include CrylA, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb, and CryIF proteins or toxic fragments thereof, as well as hybrids or combinations thereof, in particular CrylF protein or hybrids derived from CrylF protein (e.g., hybrid CrylA-CrylF protein or toxic fragments thereof), CrylA-type proteins or toxic fragments thereof, preferably CrylAc protein or hybrids derived from CrylAc protein (e.g., hybrid CrylAb-CrylAc protein) or CrylAb or Bt2 protein or toxic fragments thereof, Cry2Ae, Cry2Af, or Cry2Ag protein or toxic fragments thereof, CrylA.105 protein or toxic fragments thereof, VIP3Aa19 protein, VIP3Aa20 protein, VIP3A protein produced in COT202 or COT203 cotton events, Estruch et al. (1996), Proc Natl Acad Sci US A. 28;93(11):5389-94 or a toxic fragment thereof, the Cry proteins described in WO 2001 / 47952, insecticidal proteins from Xenorhabdus (described in WO 98 / 50427), Serratia (particularly from S. entomophila) or Photorhabdus species strains, for example the Tc protein from Photorhabdus described in WO 98 / 08932.Also included herein are variants or mutants of any one of these proteins that differ by a few amino acids (1-10, preferably 1-5) from any of the above sequences, particularly the sequences of their toxic fragments, or that are fused to a transport peptide, such as a plastid transit peptide or another protein or peptide.

[0402] Another particularly highlighted example of such a trait is the conferring of resistance to one or more herbicides, such as imidazolinones, sulfonylureas, glyphosate, or phosphinothricin. Among DNA sequences encoding proteins that confer the trait of herbicide resistance to transformed plant cells and plants, mention may be made in particular of the bar or PAT genes or Streptomyces coelicolor genes described in WO 2009 / 152359, which confer resistance to the herbicide glufosinate, as well as genes encoding suitable EPSPS (5-enolpyruvylshikimat-3-phosphatase) enzymes, genes encoding glyphosate-N-acetyltransferase, or genes encoding glyphosate oxidoreductase, which confer resistance to EPSPS-targeting herbicides, particularly glyphosate and its salts. Further suitable herbicide tolerance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., WO 2007 / 024782), a mutant Arabidopsis ALS / AHAS gene (e.g., U.S. Pat. No. 6,855,533), a gene encoding a 2,4-D-monooxygenase that confers tolerance to 2,4-D (2,4-dichlorophenoxyacetic acid), or a gene encoding a dicamba monooxygenase that confers tolerance to dicamba (3,6-dichloro-2-methoxybenzoic acid).

[0403] Another example of such a trait is resistance to one or more plant pathogenic fungi, such as Asian soybean rust. Among DNA sequences encoding proteins that confer such disease resistance traits, reference is made in particular to genetic material from Glycine tomentella, such as any of the publicly available accessions (PI441001, PI483224, PI583970, PI446958, PI499939, PI505220, PI499933, PI441008, PI505256, or PI446961) described in WO 2019 / 103918.

[0404] More particularly highlighted examples of such properties are, for example, systemic acquired resistance (SAR), increased resistance to bacteria and / or viruses due to systemins, phytoalexins, elicitors, and resistance genes and the corresponding expressed proteins and toxins.

[0405] Particularly useful transgenic events in transgenic plants or plant cultivars that can be preferentially treated according to the invention include event 531 / PV-GHBK04 (cotton, insect control, described in WO 2002 / 040677), event 1143-14A (cotton, insect control, not deposited, described in WO 2006 / 128569); event 1143-51B (cotton, insect control, not deposited, described in WO 2006 / 128570); event 1445 (cotton, herbicide resistance, not deposited, described in U.S. Patent Application Publication No. 2002-120964 or WO 2002 / 034946); event 17053 (rice, herbicide resistance, accession number PTA-9843, WO 2010 / 128569); 117737); event 17314 (rice, herbicide resistance, accession number PTA-9844, described in WO 2010 / 117735); event 281-24-236 (cotton, insect control - herbicide resistance, accession number PTA-6233, described in WO 2005 / 103266 or U.S. Patent Application Publication No. 2005-216969); event 3006-210-23 (cotton, insect control - herbicide resistance, accession number PTA-6233, described in U.S. Patent Application Publication No. Event 3272 (corn, quality characteristics, accession number PTA-9972, described in WO 2006 / 098952 or U.S. Patent Application Publication No. 2006-230473); Event 33391 (wheat, herbicide resistance, accession number PTA-2347, described in WO 2002 / 027004); Event 40416 (corn, insect control - herbicide resistance, accession number ATCC PTA-11508, described in WO 11 / 075593); Event 43A47 (Maize, insect control - herbicide resistance, Accession No. ATCC PTA-11509, described in WO 2011 / 075595); Event 5307 (Maize, insect control, Accession No. ATCC PTA-9561, described in WO 2010 / 077816); Event ASR-368 (Bentgrass, herbicide resistance, Accession No. ATCC PTA-4816, described in U.S. Patent Application Publication No. 2006-162007 or WO 2004 / 053062); Event B16 (Maize, herbicide resistance, not accessed, described in U.S. Patent Application Publication No. 2003-126634); Event BPS-CV127-9 (Soybean, herbicide resistance, Accession No. NCIMB 41603, described in WO 2010 / 080829); event BLRl (rapeseed, male sterility restoration, accession number NCIMB 41193, described in WO 2005 / 074671), event CE43-67B (cotton, insect control, accession number DSM ACC2724, described in U.S. Patent Application Publication No. 2009-217423 or WO 2006 / 128573); Event CE44-69D (cotton, insect control, not deposited, described in U.S. Patent Application Publication No. 2010-0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO 2006 / 128571); Event CE46-02A (cotton, insect control, not deposited, described in WO 2006 / 128572); Event COT102 (cotton, insect control, not deposited, described in U.S. Patent Application Publication No. 2006-130175 or WO 2004 / 039986) Event COT202 (cotton, insect control, not deposited, described in U.S. Patent Application Publication No. 2007-067868 or WO 2005 / 054479); Event COT203 (cotton, insect control, not deposited, described in WO 2005 / 054480); Event DAS21606-3 / 1606 (soybean, herbicide resistance, accession number PTA-11028, described in WO 2012 / 033794), Event DAS40278 (corn, herbicide resistance, accession number ATCC PTA-10244, described in WO 2011 / 022469); event DAS-44406-6 / pDAB8264.44.06.l (soybean, herbicide resistance, accession number PTA-11336, described in WO 2012 / 075426); event DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide resistance, accession number PTA-11335, described in WO 2012 / 075429); event DAS-59122-7 (maize, insect control - herbicide resistance, accession number ATCC PTA 11384, described in U.S. Patent Application Publication No. 2006-070139); Event DAS-59132 (corn, insect control - herbicide resistance, not accessed, described in International Publication No. WO 2009 / 100188); Event DAS68416 (soybean, herbicide resistance, accession number ATCC PTA-10442, WO 2011 / 066384 or WO 2011 / 066360); Event DP-098140-6 (corn, herbicide tolerance, accession number ATCC PTA-8296, described in U.S. Patent Application Publication No. 2009-137395 or WO 08 / 112019); Event DP-305423-1 (soybean, quality attributes, not accessed, described in U.S. Patent Application Publication No. 2008-312082 or WO 2008 / 054747); Event DP-32138-1 (corn, hybridization system, accession number ATCC PTA-9158, described in U.S. Patent Application Publication No. 2009-0210970 or WO 2009 / 103049); Event DP-356043-5 (soybean, herbicide tolerance, accession number ATCC PTA-8287, described in U.S. Patent Application Publication No. 2010-0184079 or WO 2008 / 002872; event EE-I (eggplant, insect control, not accessed, described in WO 07 / 091277); event Fil 17 (corn, herbicide resistance, accession number ATCC 209031, described in U.S. Patent Application Publication No. 2006-059581 or WO 98 / 044140); event FG72 (soybean, herbicide resistance, accession number PTA-11041, described in WO 2011 / 063413), event GA21 (corn, herbicide resistance, accession number ATCC 209033, described in U.S. Patent Application Publication No. 2005-086719 or WO 98 / 044140); event GG25 (corn, herbicide resistance, accession number ATCC 209032, described in U.S. Patent Application Publication No. 2005-188434 or WO 98 / 044140); event GHB119 (cotton, insect control - herbicide resistance, accession number ATCC PTA-8398, described in WO 2008 / 151780 event GHB614 (cotton, herbicide resistance, accession number ATCC PTA-6878, described in U.S. Patent Application Publication No. 2010-050282 or WO 2007 / 017186); event GJ11 (corn, herbicide resistance, accession number ATCC 209030, described in U.S. Patent Application Publication No. 2005-188434 or WO 98 / 044140); event GM RZ13 (sugar beet, virus resistance, accession number NCIMB-41601, described in WO 2010 / 076212); event H7-l (sugar beet, herbicide resistance, accession number NCIMB 41158 or NCIMB 41159, described in U.S. Patent Application Publication No. 2004-172669 or WO 2004 / 074492); event JOPLINl (wheat, disease resistance, not described in U.S. Patent Application Publication No. 2008-064032); event LL27 (soybean, herbicide resistance, accession number NCIMB 41658, described in WO 2006 / 108674 or U.S. Patent Application Publication No. 2008-320616); event LL55 (soybean, herbicide resistance, accession number NCIMB 41660, described in WO 2006 / 108675 or U.S. Patent Application Publication No. 2008-196127); event LLcotton25 (cotton, herbicide resistance, accession number ATCC PTA-3343, described in WO 2003 / 013224 or U.S. Patent Application Publication No. 2003-097687); event LLRICE06 (rice, herbicide tolerance, accession number ATCC 203353, described in U.S. Patent No. 6,468,747 or WO 2000 / 026345); event LLRice62 (rice, herbicide tolerance, accession number ATCC 203352, described in WO 2000 / 026345), event LLRICE601 (rice, herbicide tolerance, accession number ATCC PTA-2600, described in U.S. Patent Application Publication No. 2008-2289060 or WO 2000 / 026356); event LY038 (maize, quality traits, accession number ATCC PTA-5623, as described in U.S. Patent Application Publication No. 2007-028322 or WO 2005 / 061720); Event MIR162 (corn, insect control, Accession No. PTA-8166, described in U.S. Patent Application Publication No. 2009-300784 or WO 2007 / 142840); Event MIR604 (corn, insect control, not deposited, described in U.S. Patent Application Publication No. 2008-167456 or WO 2005 / 103301); Event MON15985 (cotton, insect control, accession No. ATCC PTA-2516, described in U.S. Patent Application Publication No. 2004-250317 or WO 2002 / 100163); Event MON810 (corn, insect control, not deposited, described in U.S. Patent Application Publication No. 2002-102582); Event MON863 (corn, insect control, accession No. ATCC PTA-2605, described in International Publication No. 2004 / 011601 or U.S. Patent Application Publication No. 2006-095986); Event MON87427 (maize, pollination control, accession number ATCC PTA-7899, Event MON87460 (maize, stress tolerance, accession number ATCC PTA-8910, described in WO 2009 / 111263 or U.S. Patent Application Publication No. 2011-0138504); Event MON87701 (soybean, insect control, accession number ATCC PTA-8194, described in U.S. Patent Application Publication No. 2009-130071 or WO 2009 / 064652); Event MON87705 (soybean, quality traits - herbicide tolerance, accession number ATCC PTA-9241, described in U.S. Patent Application Publication No. 2010-0080887 or WO 2010 / 037016); Event MON87708 (soybean, herbicide tolerance, accession number ATCC PTA-9670, described in WO 2011 / 034704); Event MON87712 (soybean, yield, Accession No. PTA-10296, described in WO 2012 / 051199); Event MON87754 (soybean, quality attributes, Accession No. ATCC PTA-9385, described in WO 2010 / 024976); Event MON87769 (soybean, quality attributes, Accession No. ATCC PTA-8911, described in U.S. Patent Application Publication No. 2011-0067141 or WO 2009 / 102873); Event M ON88017 (maize, insect control - herbicide resistance, accession number ATCC PTA-5582, described in U.S. Patent Application Publication No. 2008-028482 or WO 2005 / 059103); event MON88913 (cotton, herbicide resistance, accession number ATCC PTA-4854, described in WO 2004 / 072235 or U.S. Patent Application Publication No. 2006-059590); event MON88302 (rapeseed, herbicide resistance, accession number PTA-10955, described in WO 2011 / 153186), event MON88701 (cotton, herbicide resistance, accession number PTA-11754, described in WO 2012 / 134808), event MON89034 (maize, insect control, accession number ATCC PTA-7455, described in WO 07 / 140256 or U.S. Patent Application Publication No. 2008-260932); event MON89788 (soybean, herbicide-resistant, accession number ATCC PTA-6708, described in U.S. Patent Application Publication No. 2006-282915 or WO 2006 / 130436); event MSl 1 (rapeseed, Event MS8 (rapeseed, pollination control-herbicide resistance, accession number ATCC PTA-850 or PTA-2485, described in WO 2001 / 031042); Event MS8 (rapeseed, pollination control-herbicide resistance, accession number ATCC PTA-730, described in WO 2001 / 041558 or U.S. Patent Application Publication No. 2003-188347); Event NK603 (maize, herbicide resistance, accession number ATCC PTA-2478, described in U.S. Patent Application Publication No. 2007-292854); Event PE-7 (rice, insect control, not accessed, described in WO 2008 / 114282); Event RF3 (rapeseed, pollination control-herbicide resistance, accession number ATCC PTA-730, described in WO 2001 / 041558 or U.S. Patent Application Publication No. 2003-188347; event RT73 (rapeseed, herbicide-resistant, not accessed, described in WO 2002 / 036831 or U.S. Patent Application Publication No. 2008-070260); event SYHT0H2 / SYN-000H2-5 (soybean, herbicide-resistant, accession number PTA-11226, WO 2012 / 0825 48), event T227-1 (sugar beet, herbicide resistance, not deposited, described in WO 2002 / 44407 or U.S. Patent Application Publication No. 2009-265817); event T25 (corn, herbicide resistance, not deposited, described in U.S. Patent Application Publication No. 2001-029014 or WO 2001 / 051654); event T304-40 (cotton, insect control - herbicide resistance, accession number ATCC PTA-8171, described in U.S. Patent Application Publication No. 2010-077501 or WO 2008 / 122406; Event T342-142 (cotton, insect control, not deposited, described in WO 2006 / 128568); Event TC1507 (corn, insect control - herbicide resistance, not deposited, described in U.S. Patent Application Publication No. 2005-039226 or WO 2004 / 099447); Event VIP1034 (corn, insect control - herbicide resistance, accession number ATCC PTA-3925, described in WO 2003 / 052073), event 32316 (maize, insect control - herbicide resistance, accession number PTA-11507, described in WO 2011 / 084632), event 4114 (maize, insect control - Event EE-GM3 / FG72 (soybean, herbicide-resistant, ATCC accession number PTA-11506, described in WO 2011 / 084621), event EE-GM3 / FG72 (soybean, herbicide-resistant, ATCC accession number PTA-11041), optionally stacked in event EE-GM1 / LL27 or event EE-GM2 / LL55 (WO 2011 / 063413A2), event DAS-68416-4 (soybean, herbicide-resistant, ATCC accession number PTA-10442, WO 2011 / 066360(Al)), Event DAS-68416-4 (soybean, herbicide resistance, ATCC Accession No. PTA-10442, WO 2011 / 066384(Al)), Event DP-040416-8 (maize, insect control, ATCC Accession No. PTA-11508, WO 2011 / 075593(Al)), Event DP-043A47-3 (maize , insect control, ATCC Accession No. PTA-11509, WO 2011 / 075595(Al)), Event DP-004114-3 (maize, insect control, ATCC Accession No. PTA-11506, WO 2011 / 084621(Al)), Event DP-032316-8 (maize, insect control, ATCC Accession No. PTA-11507, WO 2011 / 084632(Al)), Event M ON-88302-9 (rapeseed, herbicide tolerance, ATCC accession number PTA-10955, WO 2011 / 153186(A1)), event DAS-21606-3 (soybean, herbicide tolerance, ATCC accession number PTA-11028, WO 2012 / 033794(A2)), event MON-87712-4 (soybean, quality characteristics, ATCC accession number PTA-10296, WO 2012 / 051199(A2)) No.), Event DAS-44406-6 (Soybean, stacked variety, herbicide resistance, ATCC Accession No. PTA-11336, International Publication No. 2012 / 075426(Al)), Event DAS-14536-7 (Soybean, stacked variety, herbicide resistance, ATCC Accession No. PTA-11335, International Publication No. 2012 / 075429(Al)), Event SYN-000H2-5 (Soybean, herbicide resistance, ATCC Accession No. PTA-11226, International Publication No. International Publication No. 2012 / 082548(A2)), Event DP-061061-7 (rapeseed, herbicide-resistant, no accession number, International Publication No. 2012071039(Al)), Event DP-073496-4 (rapeseed, herbicide-resistant, no accession number, US Patent Application Publication No. 2012 / 131692), Event 8264.44.06.1 (soybean, stacked varieties, herbicide-resistant, accession number PTA-11336, International Publication No. 201207542 6(A2)), Event 8291.45.36.2 (soybean, stacked variety, herbicide resistant, Accession No. PTA-11335, WO 2012075429(A2)), Event SYHT0H2 (soybean, ATCC Accession No. PTA-11226, WO 2012 / 082548(A2)), Event MON88701 (cotton, ATCC Accession No. PTA-11754, WO 2012 / 134808(A1)), Event KK179-2 (alfalfa, ATCC accession number PTA-11833, WO 2013 / 003558(Al)), event pDAB8264.42.32.1 (soybean, stacked variety, herbicide resistant, ATCC accession number PTA-11993, WO 2013 / 010094(Al)), event MZDT09Y (maize, ATCC accession number PTA-13025, WO 2013 / 012775(Al)).

[0406] Additionally, a list of such transgenic events is provided by the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) and can be found on the World Wide Web at its website at aphis.usda.gov. This application relates to the status of such list as is / was on the filing date of this application.

[0407] The genes / events that confer the desired trait of interest may also be present in combination with each other in transgenic plants. Examples of transgenic plants that may be mentioned are important crop plants, including cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas, other vegetables, cotton, tobacco, rapeseed, and fruit trees (including apples, pears, citrus fruits, and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco, and rapeseed. Particularly emphasized traits are increased plant resistance to insects, arachnids, nematodes, slugs, and snails, and increased plant resistance to one or more herbicides.

[0408] Commercially available examples of such plants, plant parts, or plant seeds that can be preferentially treated in accordance with the present invention include commercial products such as plant seeds sold or distributed under the trade names (GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLE PRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, ROUNDUP READY® 2 XTEND™, INTACTA RR2 PRO®, VISTIVE GOLD®, and / or XTENDFLEX™).

[0409] pathogen Non-limiting examples of fungal disease pathogens that can be treated according to the present invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, such as Blumeria graminis, Podosphaera species, such as Podosphaera leucotricha, Sphaerotheca species, such as Sphaerotheca fuliginea, Uncinula species, such as Uncinula necator;

[0410] Rust pathogens, such as Gymnosporangium species (e.g., Gymnosporangium sabinae), Hemileia species (e.g., Hemileia vastatrix), Phakopsora species (e.g., Phakopsora pachyrhizi or Phakopsora meibomiae), Puccinia species (e.g., Puccinia recondita, Puccinia graminis, or Puccinia striiformis), striiformis), diseases caused by Uromyces species (e.g., Uromyces appendiculatus);

[0411] For example, Albugo species (e.g., Albugo candida), Bremia species (e.g., Bremia lactucae), Peronospora species (e.g., Peronospora pisi or P. brassicae), Phytophthora species (e.g., Phytophthora infestans), Plasmopara species (e.g., Plasmopara viticola), Pseudoperonospora species (e.g., Pseudoperonospora humuli or P. humuli), Diseases caused by pathogens of the oomycete group, such as Pseudoperonospora cubensis, Pythium species (e.g., Pythium ultimum);

[0412] For example, Alternaria species, such as Alternaria solani, Cercospora species (e.g. Cercospora beticola), Cladosporium species (e.g. Cladosporium cucumerinum), Cochliobolus species (e.g. Cochliobolus sativus (conidial morphology: Drechslera, synonym: Helminthosporium) or Cochliobolus miyabeanus), Colletotrichum species (e.g. Colletotrichum Colletotrichum lindemuthanium), Corynespora species (e.g., Corynespora cassiicola), Cycloconium species (e.g., Cycloconium oleaginum), Diaporthe species (e.g., Diaporthe citri), Elsinoe species (e.g., Elsinoe fawcettii), Gloeosporium species (e.g., Gloeosporium laeticolor), Glomerella species (e.g., Glomerella cingulata), cingulata), Guignardia species (e.g., Guignardia bidwelli), Leptosphaeria species (e.g., Leptosphaeria maculans), Magnaporthe species (e.g., Magnaporthe grisea), Microdochium species (e.g., Microdochium nivale), Mycosphaerella species (e.g., Mycosphaerella graminicola,), Mycosphaerella arachidicola, or Mycosphaerella fijiensis), Phaeosphaeria species (e.g., Phaeosphaeria nodorum), Pyrenophora species (e.g., Pyrenophora teres or Pyrenophora tritici repentis), Ramularia species, for example, Ramularia collo-cygni or Ramularia areola), Rhynchosporium species (e.g., Rhynchosporium secharis), Brown spot and damping-off caused by Septoria species (e.g., Septoria apii or Septoria lycopersici), Stagonospora species (e.g., Stagonospora nodorum), Typhula species (e.g., Typhula incarnata), and Venturia species (e.g., Venturia inaequalis);

[0413] For example, Corticium species (e.g., Corticium graminearum), Fusarium species (e.g., Fusarium oxysporum), Gaeumannomyces species (e.g., Gaeumannomyces graminis), Plasmodiophora species (e.g., Plasmodiophora brassicae), Rhizoctonia species (e.g., Rhizoctonia solani), Sarocladium species (e.g., Sarocladium oryzae), oryzae), Sclerotium species (e.g., Sclerotium oryzae), Tapesia species (e.g., Tapesia acuformis), Thielaviopsis species (e.g., Thielaviopsis basicola; Root and stem diseases caused by:

[0414] For example, Alternaria species (e.g., Alternaria spp.), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium cladosporioides), Claviceps species (e.g., Claviceps purpurea), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Monographella species (e.g., Monographella nivalis), nivalis), diseases of ears and panicles (including corn cobs) caused by Stagnospora species (e.g., Stagnospora nodorum);

[0415] diseases caused by smut fungi, such as Sphacelotheca species (e.g., Sphacelotheca reiliana), Tilletia species (e.g., Tilletia caries or Tilletia controversa), Urocystis species (e.g., Urocystis occulta), and Ustilago species (e.g., Ustilago nuda);

[0416] For example, Aspergillus species (e.g., Aspergillus flavus), Botrytis species (e.g., Botrytis cinerea), Monilinia species (e.g., Monilinia laxa), Penicillium species (e.g., Penicillium expansum or Penicillium purpurogenum), Rhizopus species (e.g., Rhizopus stolonifer), Sclerotinia species (e.g., Sclerotinia sclerotiorum), sclerotiorum), fruit rot caused by Verticilium species (e.g., Verticilium alboatrum);

[0417] For example, Alternaria species (e.g., Alternaria brassicicola), Aphanomyces species (e.g., Aphanomyces euteiches), Ascochyta species (e.g., Ascochyta lentis), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium herbarum), Cochliobolus species (e.g., Cochliobolus sativus (conidiomorph: Drechslera, Bipolaris (synonym: Helminthosporium)), Colletotrichum species (e.g., Colletotrichum coccodes), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Macrohomina species (e.g., Macrohomina phaseolina), phaseolina), Microdochium species (e.g., Microdochium nivale), Monographella species (e.g., Monographella nivalis), Penicillium species (e.g., Penicillium expansum), Phoma species (e.g., Phoma lingam), Phomopsis species (e.g., Phomopsis sojae), Phytophthora species (e.g., Phytophthora cactorum), Pyrenophora species (e.g., Pyrenophora graminea), Pyricularia species (e.g., Pyricularia oryzae), Pythium species (e.g., Pythium ultimum), Rhizoctonia species (e.g., Rhizoctonia solani), Rhizopus species (e.g., Rhizopus oryzae), Sclerotium species (e.g., Sclerotium rolfsii), Septoria species (e.g., Septoria nodorum), Seed- and soil-borne rot and damping-off caused by Typhula species (e.g., Typhula incarnata) and Verticillium species (e.g., Verticillium dahliae), as well as seedling diseases;

[0418] For example, cancer, gall, and witches' broom caused by Nectria species (e.g., Nectria galligena); For example, damping-off caused by Verticillium species (e.g., Verticillium longisporum), Fusarium species (e.g., Fusarium oxysporum); For example, deformation of leaves, flowers, and fruits caused by Exobasidium species (e.g., Exobasidium vexans) and Taphrina species (e.g., Taphrina deformans); For example, degenerative diseases of woody plants caused by Esca species (e.g., Phaeomoniella chlamydospora, Phaeoacremonium aleophilum, or Fomitiporia mediterranea), Ganoderma species (e.g., Ganoderma boninense);

[0419] For example, diseases of plant tubers caused by Rhizoctonia species (e.g., Rhizoctonia solani), Helminthosporium species (e.g., Helminthosporium solani); Bacterial pathogens, such as Xanthomonas species (e.g., Xanthomonas campestris pv. oryzae), Pseudomonas species (e.g., Pseudomonas syringae pv. lachrymans), Erwinia species (e.g., Erwinia amylovora), Liberibacter species (e.g., Liberibacter asiaticus), Xylella species (e.g., Xylella fastidiosa), Diseases caused by Ralstonia species (e.g., Ralstonia solanacearum), Dickeya species (e.g., Dickeya solani), Clavibacter species (e.g., Clavibacter michiganensis), and Streptomyces species (e.g., Streptomyces scabies).

[0420] Soybean diseases: For example, black spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var.truncatum), brown spot (Septoria glycines), sugar beet brown spot and blight (Cercospora kikuchii), Corephora damping-off (Coanephora infungibrifera trispora (synonym)), Dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), Drexlera blight (Drechslera glycini), red star spot (Cercospora sojina), Leptosphaerulina leaf spot (Leptosphaerulina trifolii) trifolii), Phyllosticta leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), soybean leaf rot, foliage, and spider web disease (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), soybean rot (Sphaceloma glycines). Fungal diseases of leaves, stems, pods, and seeds caused by Fusarium glycines), Stemphylium damping-off (Stemphylium botryosum), Sudden Withering Syndrome (Fusarium virguliforme), and Corynespora cassiicola.

[0421] Fungal diseases of the roots and stem bases include, for example, black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), scab or damping-off, root rot, as well as sheath and neck rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora basinfecta), and the like. vasinfecta), sheath and stem blight (Diaporthe phaseolorum), branch blight (Diaporthe phaseolorum var. caulivora), Phytophthora rot (Phytophthora megasperma), leaf drop (Phialophora gregata), mildew rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum). It is caused by Rhizoctonia rot, stem rot and damping-off (Rhizoctonia solani), Sclerotinia stem rot (Sclerotinia sclerotiorum), southern blight (Sclerotinia rolfsii), and Thielaviopsis root rot (Thielaviopsis basicola).

[0422] mycotoxins Additionally, the compounds of formula (I) and compositions of the present invention may reduce the mycotoxin content in harvested materials and in foods and feeds prepared therefrom. Mycotoxins include, in particular, but are not limited to, deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2-toxin and HT2-toxin, fumonisins, zearalenone, moniliformin, fusarin, diacetoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxin, patulin, ergot alkaloids, and aflatoxins, which may be produced, for example, by the following fungi: Fusarium species, such as Fusarium acuminatum, Fusarium asiaticum, Fusarium avenaceum, Fusarium crookwellense, Fusarium culmorum, Fusarium spp. culmorum), Fusarium graminearum (Gibberella zeae), Fusarium equiseti, Fusarium fujikoroi, Fusarium musarum, Fusarium oxysporum, Fusarium proliferatum, Fusarium poae, Fusarium pseudograminearum, Fusarium sambucinum, Fusarium scirpi, It can be produced by Fusarium semitectum, Fusarium solani, Fusarium sporotrichoides, Fusarium langsethiae, Fusarium subglutinans, Fusarium tricinctum, Fusarium verticillioides; and also by Aspergillus species, such as Aspergillus flavus, Aspergillus parasiticus, Aspergillus nomius, Aspergillus ochraceus, Aspergillus clavatus, Aspergillus terreus. terreus, Aspergillus versicolor, Penicillium species such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps species such as C. purpurea, C. fusiformis, C. paspali, C. africana, africana, Stachybotrys species, and other fungi.

[0423] Material Protection The compounds of formula (I) and compositions of the invention may also be used in the protection of materials, in particular industrial materials, against attack and destruction by phytopathogenic fungi.

[0424] Additionally, the compounds of formula (I) and compositions of the present invention can be used alone or in combination with other active ingredients as antifouling compositions.

[0425] In the context of the present invention, industrial materials are understood to mean inanimate materials prepared for industrial use. For example, industrial materials to be protected from microbial deterioration or destruction may be adhesives, glues, paper, wallpaper, and board / cardboard, textiles, carpets, leather, wood, textiles and tissues, paints and plastic products, cooling lubricants, and other products that may be infected or destroyed by microorganisms. Components of production plants and buildings that may be damaged by microbial growth, such as cooling water circuits, cooling and heating systems, ventilation and air conditioning units, may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants, and transport fluids, more preferably wood.

[0426] The compounds of formula (I) and compositions of the present invention can prevent adverse effects such as rotting, decay, discolouration, bleaching or mould formation.

[0427] In the case of wood treatment, the compounds of formula (I) and compositions of the present invention may also be used against fungal diseases which tend to grow on or in timber.

[0428] Timber refers to all types of wood and all types of construction wood functions, such as hardwood, high-density wood, laminated board, and plywood.Furthermore, the compound of formula (I) and the composition of the present invention can be used to protect objects that come into contact with salt water or brackish water, especially ship hulls, screens, nets, buildings, mooring systems, and signaling systems, from fouling.

[0429] The compound of formula (I) and the composition of the present invention can also be used to protect stored goods.Stored goods are understood to mean natural substances of plant or animal origin or their processed products of natural origin that are desired to be long-term protected.Plant-derived stored goods, such as plants or plant parts such as stems, leaves, tubers, seeds, fruits, and grains, can be protected in the freshly harvested state or after processing by (pre)drying, wetting, crushing, grinding, pressing, or roasting.Stored goods also include raw wood, such as construction lumber, utility poles, and barriers, or lumber in the form of finished products, such as furniture.Stored goods of animal origin are, for example, hides, leather, fur, and hair.The compound of formula (I) and the composition of the present invention can prevent adverse effects such as decay, decay, discoloration, bleaching, or mold formation.

[0430] Microorganisms capable of decomposing or degrading industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime organisms. The compounds of formula (I) and compositions of the present invention preferably act against fungi, especially molds, wood-staining fungi, and wo...

Claims

1. Formula (I): 【Chemical 1】 (In the formula, A １ is N or CR ８ and A 2 is O, NR 1 , or CR 2A R R2B ; R 1 , R 2A and R 2B are independently of one another hydrogen or C 1 -C 4 -alkyl; m is 0 or 1; T is hydrogen; R 3 and R 4 are independently hydrogen, fluoro, or C 1 -C 4 -alkyl; and R 5 is hydrogen; L is a direct bond or methylene; R ６ is phenyl, naphthyl, thienyl, furanyl, indolyl or benzofuranyl, The phenyl, naphthyl, thienyl, furanyl, indolyl, or benzofuranyl may be selected from the group consisting of 1 to 3 R ６Ｓ optionally substituted with a substituent; R ６Ｓ are independently selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, and pyrazolyl; Ring Y, together with the pyridine ring or pyridazine ring, represents a group represented by formula (II-a), (II-g), (II-h), (II-r), or (II-v), respectively: 【Chemistry 2】 (In the formula, ＊ is the point of attachment to the -O-Q group, # is the point of attachment to another heterocycle; p is 0, 1, or 2; x １ is 1 or 2, R ７Ａ , R ７Ｂ , R ７Ｃ , R ７Ｄ , R ７Ｅ , R ７Ｆ , and R ７Ｇ are independently hydrogen, C １ -C ４ - alkyl, or C １ -C ４ -haloalkyl, R ７Ｈ is hydrogen, C １ -C ４ - alkyl, or C １ -C ４ -haloalkyl, R ７Ｋ is C １ -C ４ -alkyl), R ８ is hydrogen, Q is phenyl, thienyl, or pyridyl; The phenyl, thienyl, and pyridyl may optionally contain one or two substituents Q Ｓ is replaced by Q Ｓ is a halogen, C １ -C ４ -Alkyl, C １ -C ４ -haloalkyl, C ２ -C ４－ Alkenyl, C ２ -C ４－ Haloalkenyl, C ２ -C ４ -alkynyl, C ２ -C ４ -haloalkynyl, and C ３ -C ６ -cycloalkyl) The compound or a salt thereof, a hydrate, or a hydrate of said salt.

2. L is a direct bond or methylene, and R ６ is phenyl, Phenyl may have one or two R ６Ｓ optionally substituted with a substituent; R ６Ｓ is fluoro, chloro, bromo, C １ -C ４ -Alkyl, difluoromethyl, trifluoromethyl, C １ -C ４ -alkoxy, C ２ -C ４ -alkenyl, C ２ -C ４ - independently selected from the group consisting of alkynyl, cyclopropyl, cyclobutyl, and pyrazolyl; Pyrazolyl is similarly C １ -C ４ 2. The compound of formula (I) of claim 1, optionally substituted with one substituent independently selected from the group consisting of: -alkyl.

3. A １ is N or CR ８ and R ８ is hydrogen, and Q is phenyl, which is substituted with one or two substituents Q Ｓ is replaced by Q Ｓ is halogen, methyl, ethyl, difluoromethyl, trifluoromethyl, C ２ -C ４ -alkenyl, C ２ -C ４ 3. A compound of formula (I) according to claim 1, wherein each of the aryl groups is independently selected from the group consisting of alkynyl, cyclopropyl, and cyclobutyl.

4. The ring Y, together with the pyridine ring or pyridazine ring, is represented by the formula (II-a), (II-g), (II-h), or (II-r), respectively: 【Chemistry 3】 (In the formula, ＊ is the point of attachment to the -O-Q group, # is the point of attachment to another heterocycle; p is 0 or 1; x １ is 1 or 2, R ７Ａ is hydrogen, R ７Ｂ is hydrogen or C １ -C ４ - alkyl, R ７Ｃ is hydrogen, R ７Ｄ is hydrogen, R ７Ｅ is hydrogen, R ７Ｆ is hydrogen, R ７Ｋ is C １ -C ４ 4. A compound of formula (I) according to claim 1, wherein the compound forms a group of formula (I) -alkyl.

5. The compound of formula (I) according to any one of claims 1 to 4, wherein A 2 is oxygen (O).

6. A composition for controlling phytopathogenic harmful fungi, comprising at least one compound of formula (I) according to any one of claims 1 to 5 and at least one carrier and / or surfactant.

7. 10. A method for controlling harmful microorganisms in crop protection and material protection, characterized in that at least one compound of formula (I) according to any one of claims 1 to 5 and / or a composition according to claim 6 is applied to the harmful microorganisms and / or their habitat.

8. Use of one or more compounds of formula (I) according to any one of claims 1 to 5 and / or compositions according to claim 6 for controlling harmful microorganisms in crop protection and material protection.

9. Formula (I-a-1): 【Chemistry 4】 (In the formula, 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 5, and A ２ is oxygen (O), T is hydrogen, and m is 1 or 2, In process A), a compound of formula (1): 【Chemistry 5】 (In the formula, A １ , ring Y, p, R ７ and Q is defined as in formula (I-a-1), and U １ is hydroxyl, halogen, or C １ -C ６ -alkoxy) Formula (2): 【Chemistry 6】 (In the formula, m, R ３ , R ４ , R ５ , L, and R ６ is defined as in formula (I-a-1), and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl, Formula (3): 【Chemistry 7】 (In the formula, m, A １ , R ３ , R ４ , R ５ , L, R ６ , ring Y, p, R ７ and Q is defined as in formula (I-a-1), and W is defined as in formula (2), The phthalimide group is removed from the compound of formula (3) to obtain a compound of formula (4): 【Chemistry 8】 (In the formula, m, A １ , R ３ , R ４ , R ５ , L, R ６ , ring Y, p, R ７ , Q, and W are defined as in formula (3), and cyclizing the compound of formula (4), 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 (I-a-1). or When W is tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl, the compound of formula (4) is treated with a dehydrating agent, optionally in the presence of a base, followed by a deprotection step to obtain the compound of formula (I-a-1). Or in process B), formula (5): 【Chemistry 9】 (In the formula, A １ , ring Y, p, and R ７ is defined as in formula (I-a-1), and X is a halogen, and U １ is hydroxyl, halogen, or C １ -C ６ -alkoxy) Formula (2): 【Chemistry 10】 (In the formula, m, R ３ , R ４ , R ５ , L, and R ６ is defined as in formula (I-a-1), and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl, Formula (6a): 【Chemistry 11】 (In the formula, m, A １ , R ３ , R ４ , R ５ , L, R ６ , ring Y, p, R ７ , X, and W are defined as above, The phthalimide group is removed from the compound of formula (6a) to obtain a compound of formula (6b): 【Chemistry 12】 (In the formula, m, A １ , R ３ , R ４ , R ５ , L, R ６ , ring Y, p, R ７ , X and W are defined as in formula (6a), The compound of formula (6b) is cyclized to When W is hydrogen, the compound of formula (6b) is treated with a dehydrating agent, optionally in the presence of a base, to give the compound of formula (7): 【Chemistry 13】 (In the formula, m, A １ , R ３ , R ４ , R ５ , L, R ６ , ring Y, p, R ７ and X is defined as above, or When W is tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl, the compound of formula (6b) is treated with a dehydrating agent, optionally in the presence of a base, followed by a deprotection step to obtain the compound of formula (7); and the compound of formula (7) is converted into a compound of formula (8): 【Chemistry 14】 wherein Q is as defined above, with a compound of formula (I-a-1) in the presence of a base, and optionally in the presence of a suitable copper salt or complex, to obtain a compound of formula (I-a-2).

10. Formula (3) or Formula (4): 【Chemistry 15】 (In the formula, 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 5, m is 1 or 2; and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

11. Formula (7): 【Chemistry 16】 (In the formula, A １ , R ３ , R ４ , R ５ , L, R ６ , ring Y, p, and R ７ is defined in any one of claims 1 to 5, m is 1 or 2; and X is a halogen.

12. Formula (10) or Formula (12): 【Chemistry 17】 (In the formula, 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 5, m is 1 or 2; E １ is hydroxyl or halogen, E ２ is hydroxyl or amino, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

13. Formula (14) or Formula (15): 【Chemistry 18】 (In the formula, A １ , R ３ , R ４ , R ５ , L, R ６ , ring Y, p, and R ７ is defined in any one of claims 1 to 5, m is 1 or 2; X is a halogen; E １ is hydroxyl or halogen, E ２ is hydroxyl, and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl, or (4-methoxyphenyl)methyl.

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