Azanicyclic (thio)amides as fungicidal compounds

Abstract

The present invention relates to azabicyclic (thio)amide compounds and their use for controlling plant pathogenic microorganisms, such as plant pathogenic fungi, as well as to processes and intermediates for preparing these compounds.

Description

[Technical Field]

[0001] This invention relates to azanicyclic (thio)amide compounds and their use for controlling plant pathogenic microorganisms such as plant pathogenic fungi. It also relates to processes and intermediates for preparing these compounds. [Background technology]

[0002] Numerous crop protection agents have been developed to combat or prevent the spread of microorganisms. However, there remains a need to develop novel compounds themselves to provide compounds that are effective against a wide range of plant pathogenic microorganisms, such as fungi, are low in toxicity, highly selective, or can be used at low application rates, while simultaneously enabling effective pest control. It may also be 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, and in at least some of these embodiments, they have advantages over known compounds and compositions.

[0004] Pyridazinamide as a fungicide is disclosed in International Publication No. 2020 / 109391. [Modes for carrying out the invention]

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

[0006] [ka]

[0007] (In the formula, T is oxygen (O) or sulfur (S), n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR 8 And, R 8is hydrogen, halogen, cyano, or C1-C4-alkyl, R 1 is hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 , -S(=O)2R 12 , -C(=O)N(R 13 )2, or -S(=O)2N(R 14 )2, and R 10 , R 11 , and R 12 are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl, R 13 and R 14 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl, R 2 and R 3 are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, or C3-C8-cycloalkyl, or or R 2 and R 3 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclyl ring, R 4 and R 5 are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, or C3-C8-cycloalkyl, or or R 4 and R 5These, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclyl ring. or R 2 and R 4 These, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclyl ring. and R 3 and R 5 These are independently hydrogen or halogen, or R 2 and R 4 The formula ** -C(R 3 )=C(R 5 )- ## (In the ceremony ** is N(R 1 It is a connection point to ), ## is R 6 Forms the base of (which is a bonding point to), and R 3 and R 5 These are independently hydrogen, halogen, or C1-C6-alkyl, R 6 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, C1-C3-alkoxy, or C1-C3-haloalkoxy, C1-C3-alkoxy and C1-C3-haloalkoxy are C3-C 12 -Carbocyclyl, C6-C 14 - Independently substituted with one substituent selected from the group consisting of aryls, 3- to 14-membered heterocyclines, and 5- to 14-membered heteroaryls, Said C3-C12 -Carbocyclyl, C6-C 14 -aryls, 3- to 14-membered heterocyclines, and 5- to 14-membered heteroaryls are sequentially divided into 1 to 4 R 6S Substituting as desired with substituents, 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, and 3- to 14-membered heterocyclyloxy have 1 to 4 R 6S Substituting as desired with substituents, R 6S These are independently halogen, cyano, isocyano, 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, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6 -Alkyl sulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5-membered or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -N(R) 15 )2, -C(=O)R 16 , -C(=O)(OR 17 ), -C(=O)N(R 18 )2, -S(=O)2N(R 19 )2, -O-Si(C1-C6-alkyl)3, or -Si(C1-C6-alkyl)3, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkyls The ruhonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are further optionally substituted with 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-membered to 7-membered heterocyclyl. and The aforementioned C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5-membered or 6-membered heteroaryl, and 3- to 7-membered heterocyclyl are further optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl, or Two C1-C6-alkyl substituents bonded to the same carbon atom form a C3-C8-cycloalkyl ring. or 2 R 6SThe substituents, if desired, combine with the carbon atoms to which they are bonded to form a C3-C8-cycloalkyl ring. and R 15 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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-membered to 7-membered heterocyclyl groups. and The C3-C8-cycloalkyl group is further optionally substituted with 1 to 4 substituents independently selected from the group consisting of 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 16 , R 17 , R 18 , and R 19 These are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl, The C1-C6-alkyl or C1-C6-haloalkyl group may be further optionally substituted with 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-membered to 7-membered heterocyclyl groups. Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. p is 0, 1, 2, 3, or 4. R 7 This includes halogens, cyano, nitro, hydroxyl, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2 or -S(=O)2N(R 24 )2, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, and C1-C6-haloalkylsulfonyl are optionally substituted with 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, and C3-C8-halocycloalkyl. C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. and R 20 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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, and C3-C8-halocycloalkyl groups. and The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 21 , R 22 , R 23 , and R 24 These are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. or Two substituents R 7 These, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring. 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 -Carbocyclyls, 3- to 14-membered heterocyclyls, and 5- to 14-membered heteroaryls include halogens, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-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-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 , -NR 26 C(=O)R 27, -C(=O)N(R 28 )2, C(=S)R 29 , -C(=S)N(R 30 )2, -C(=NR 31 )R 32 , -C(=NOR 33 )R 34 , and -N(R 35 )2, independently selected from the group consisting of 1 to 5 Q S substituents, optionally substituted, wherein the C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are optionally substituted with 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, The C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, and 5- to 14-membered heteroaryl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of 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-C6-alkenyl, and 3- to 7-membered heterocyclyl, The C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl are optionally substituted with 2 substituents which together with the carbon atom to which they are attached form a C3-C8-cycloalkyl, R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、and R 34 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, or C1-C6-alkoxy, The C1-C6-alkyl, C1-C6-haloalkyl, and C1-C6-alkoxy are optionally substituted with 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 R 35These are independently hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, or C3-C8-cycloalkyl, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, and C2-C6-haloalkenyl are optionally substituted with 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-membered to 7-membered heterocyclyl. The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl groups. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl compounds (which may be optionally substituted with two substituents that, in order, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl group), The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0008] The present invention relates to a composition comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable auxiliary agent.

[0009] The present invention also relates to the use of compounds of formula (I) as defined herein or compositions as defined herein for the control of plant pathogenic fungi.

[0010] The present invention relates to a method for controlling plant pathogenic fungi, comprising the step of applying a compound of formula (I) as defined herein or a composition as defined herein to a plant, plant part, seed, fruit, or soil in which a plant grows.

[0011] The present invention also relates to a process and intermediates for preparing the compound of formula (I).

[0012] Unless otherwise specified, the following definitions of substituents and residues apply throughout this specification and the claims. As used herein, the term "halogen" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0013] As used herein, the term "methylidene" refers to a CH2 group bonded to a carbon atom via a double bond.

[0014] As used herein, the term "halomethylidene" refers to a CX2 group bonded to a carbon atom via a double bond, where X is a halogen.

[0015] As used herein, the term "oxo" refers to an oxygen atom bonded to a carbon or sulfur atom via a double bond.

[0016] As used herein, the term "C1-C6-alkyl" refers to a saturated, branched, or linear hydrocarbon chain having 1, 2, 3, 4, 5, or 6 carbon atoms. Examples of C1-C6 alkyl groups 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, isopropyl, butyl, sec-butyl, iso-butyl, or tert-butyl.

[0017] As used herein, the terms “C3-C8-cycloalkyl” and “C3-C8-cycloalkyl ring” refer to saturated monocyclic hydrocarbon rings containing 3, 4, 5, 6, 7, or 8 carbon atoms. Examples of C3-C8-cycloalkyls include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. In particular, the cycloalkyls have 3 to 6 carbon atoms.

[0018] As used herein, the term "C3-C8-halocycloalkyl" refers to a C3-C8 cycloalkyl group in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0019] As used herein, the term “C2-C6-alkenyl” 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-alkenyls include ethenyl (or “vinyl”) group, propa-2-en-1-yl (or “allyl”) group, propa-1-en-1-yl group, buto-3-enyl group, buto-2-enyl group, buto-1-enyl group, pento-4-enyl group, pento-3-enyl group, pento-2-enyl group, pento-1-enyl group, hexa-5-enyl group, hexa-4-enyl group, hexa-3-enyl group, hexa-2-enyl group, hexa-1-enyl group, propa-1-en-2-yl or "isopropenyl" group, 2-methylpropa-2-enyl group, 1-methylpropa-2-enyl group, 2-methylpropa-1-enyl group, 1-methylpropa-1-enyl group, 3-methylbuto-3-enyl group, 2-methylbuto-3-enyl group, 1-methylbuto-3-enyl group, 3-methylbuto-2-enyl group, 2-methylbuto-2-enyl group, 1-methylbuto-2-enyl group, 3-methylbuto-1-enyl group, 2-methylbuto-1-enyl group, 1-methylbuto-1-enyl group, 1,1-dimethylpropa-2-enyl group, 1-ethylpropa-1-enyl group, 1-propyl vinyl group, 1-isopropyl vinyl group, 4-methylpento-4-enyl group, 3-methylpento-4-enyl group, 2-methylpento-4-enyl group, 1-methylpento-4-enyl group, 4-methylpento-3-enyl group, 3-methylpento-3-enyl group, 2-methylpento-3-enyl group, 1-methylpento To-3-enyl group, 4-methylpento-2-enyl group, 3-methylpento-2-enyl group, 2-methylpento-2-enyl group, 1-methylpento-2-enyl group, 4-methylpento-1-enyl group, 3-methylpento-1-enyl group, 2-methylpento-1-enyl group, 1-methylpento-1-enyl group, 3-ethylbuto-3-enyl group, 2-ethylbuto-3-enyl group, 1-ethylbuto-3- Enyl group, 3-ethylbuto-2-enyl group, 2-ethylbuto-2-enyl group, 1-ethylbuto-2-enyl group, 3-ethylbuto-1-enyl group, 2-ethylbuto-1-enyl group, 1-ethylbuto-1-enyl group, 2-propylpropa-2-enyl group, 1-propylpropa-2-enyl group, 2-isopropylpropa-2-enyl group, 1-isopropylpropa-2-enyl group, 2-propylpropa Examples include, but are not limited to, the -1-enyl group, 1-propylpropa-1-enyl group, 2-isopropylpropa-1-enyl group, 1-isopropylpropa-1-enyl group, 3,3-dimethylpropa-1-enyl group, 1-(1,1-dimethylethyl)ethenyl group, buta-1,3-dienyl group, penta-1,4-dienyl group, hexa-1,5-dienyl group, or methylhexadienyl group.

[0020] As used herein, the term "C2-C6-alkynyl" refers to a branched or linear hydrocarbon chain having 2, 3, 4, 5, or 6 carbon atoms and containing at least one triple bond. Examples of C2-C6 alkynyls include ethynyl group, propa-1-inyl group, propa-2-inyl hydrocarbon chain (or "propargyl") group, buto-1-inyl group, buto-2-inyl group, buto-3-inyl group, pento-1-inyl group, pento-2-inyl group, pento-3-inyl group, pento-4-inyl group, hexa-1-inyl group, hexa-2-inyl group, hexa-3-inyl group, hexa-4-inyl group, hexa-5-inyl group, 1-methylpropa-2-inyl group, 2-methylbuto-3-inyl group, 1-methylbuto-3-inyl group, 1-methylbuto-2-inyl group, 3-methylbuto-1-inyl group, 1-ethylpropa-2-inyl group, 3-methylpento-4-inyl group, 2 Examples include, but are not limited to, the methylpent-4-inyl group, 1-methylpent-4-inyl group, 2-methylpent-3-inyl group, 1-methylpent-3-inyl group, 4-methylpent-2-inyl group, 1-methylpent-2-inyl group, 4-methylpent-1-inyl group, 3-methylpent-1-inyl group, 2-ethylbuto-3-inyl group, 1-ethylbuto-3-inyl group, 1-ethylbuto-2-inyl group, 1-propylpropa-2-inyl group, 1-isopropylpropa-2-inyl group, 2,2-dimethylbuto-3-inyl group, 1,1-dimethylbuto-3-inyl group, 1,1-dimethylbuto-2-inyl group, or 3,3-dimethylbuto-1-inyl group.

[0021] As used herein, the term “C1-C6-haloalkyl” refers to a C1-C6-alkyl group in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different, as defined above. Examples of C1-C6-haloalkoxys 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-trifluoropropane-2-yl. Fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and 1,1,1-trifluoropropane-2-yl are preferred.

[0022] As used herein, the term “C1-C6-fluoroalkyl” refers to a C1-C6-alkyl group in which one or more hydrogen atoms are substituted with one or more fluorine atoms, which may be the same or different, as defined above. Examples of C1-C6-fluoroalkyl groups include, but are not limited to, monofluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, and 2,2,2-trifluoroethyl.

[0023] As used herein, the term "C2-C6-haloalkenyl" refers to a C2-C6-alkenyl group in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0024] As used herein, the term "C2-C6-haloalkynyl" refers to a C2-C6-alkynyl group in which two or more hydrogen atoms are substituted with one or more halogen atoms, which may be identical, as defined above. As used herein, the term "C1-C6-alkoxy" refers to a group of the formula (C1-C6-alkyl)-O-, where the term "C1-C6-alkyl" is defined herein. Examples of C1-C6-alkoxys 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 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 alkoxys as part of a complex substituent, e.g., alkoxyalkyls and alkoxyalkoxys, unless otherwise defined.

[0025] As used herein, the term "C1-C6-haloalkoxy" refers to a C1-C6-alkoxy group in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different, as defined above. Examples of C1-C6-haloalkoxys 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-trifluoropropa-2-oxy.

[0026] As used herein, the term “C3-C8-cycloalkoxy” refers to monocyclic saturated cycloalkoxy radicals 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 composite substituent, such as cycloalkoxyalkyl, unless otherwise defined.

[0027] As used herein, the term "C2-C6-alkenyloxy" refers to the group of the formula (C2-C6-alkenyl)-O-, in which the term "C1-C6-alkenyl" is defined herein. Examples of C2-C6 alkenyl groups include the ethenyloxy (or "vinyloxy") group, propa-2-en-1-yloxy (or "allyl") group, propa-1-en-1-yloxy group, buto-3-enyloxy group, buto-2-enyloxy group, buto-1-enyloxy group, pento-4-enyloxy group, pento-3-enyloxy group, pento-2-enyloxy group, pento-1-enyloxy group, hexa-5-enyloxy group, hexa-4-enyloxy group, hexa-3-enyloxy group, hexa-2-enyloxy group, hexa-1-enyloxy group, propa-1-en-2-yloxy (or "isopropenyloxy") group, 2-methylpropa-2-enyloxy group, 1-methylpropa-2-enyloxy group, 2-methylpropa-1-enyloxy group, 1-methylpropa-1-enyloxy group, 3-methylbuto-3-enyloxy group, 2-methylbuto-3-enyloxy group, 1-methylbuto-3-enyloxy group, 3-methylbuto-2-enyloxy group, 2-methylbuto-2-enyloxy group, 1-methylbuto-2-enyloxy group, 3-methylbuto-1-enyloxy group, 2-methylbuto-1-enyloxy group, 1-methylbuto-1-enyloxy group, 1,1-dimethylpropa-2-enyloxy group, 1-ethylpropa-1-enyloxy group, 1-propyl vinyloxy group, 1-isopropyl vinyloxy group, 4-methylpento-4-enyloxy group, 3-methylpento-4-enyloxy group, 2-methylpento-4-enyloxy group, 1-methylpento-4-enyloxy group, 4-methylpento-3-enyloxy group, 3-methylpento-3-enyloxy group, 2-methylpento-3-enyloxy group, 1-methylpento 3-Methylpent-3-enyloxy group, 4-methylpent-2-enyloxy group, 3-methylpent-2-enyloxy group, 2-methylpent-2-enyloxy group, 1-methylpent-2-enyloxy group, 4-methylpent-1-enyloxy group, 3-methylpent-1-enyloxy group, 2-methylpent-1-enyloxy group, 1-methylpent-1-enyloxy group, 3-ethylbuto-3-enyloxy group, 2-ethylbuto-3-enyloxy group, 1-ethylbuto- 3-enyloxy group, 3-ethylbuto-2-enyloxy group, 2-ethylbuto-2-enyloxy group, 1-ethylbuto-2-enyloxy group, 3-ethylbuto-1-enyloxy group, 2-ethylbuto-1-enyloxy group, 1-ethylbuto-1-enyloxy group, 2-propylpropa-2-enyloxy group, 1-propylpropa-2-enyloxy group, 2-isopropylpropa-2-enyloxy group, 1-isopropylpropa-2-enyloxy group, 2-propylpropa Examples include, but are not limited to, the following groups: ropa-1-enyloxy group, 1-propylpropa-1-enyloxy group, 2-isopropylpropa-1-enyloxy group, 1-isopropylpropa-1-enyloxy group, 3,3-dimethylpropa-1-enyloxy group, 1-(1,1-dimethylethyl)ethenyloxy group, buta-1,3-dienyloxy group, penta-1,4-dienyloxy group, hexa-1,5-dienyloxy group, or methylhexadienyloxy group.

[0028] As used herein, the term "C2-C6-haloalkenyloxy" refers to a (C2-C6-alkenyl)-O- group in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0029] As used herein, the term "C1-C6-alkylsulfanyl" refers to a saturated linear or branched group of the formula (C1-C6-alkyl)-S-, where the term "C1-C6-alkyl" is defined herein. Examples of C1-C6-alkylsulfanyls include, but are not limited to, methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, sec-butylsulfanyl, isobutylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, and hexylsulfanyl groups.

[0030] As used herein, the term "C1-C6-haloalkylsulfanil" refers to a C1-C6 alkylsulfanil in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0031] As used herein, the term “C3-C8-cycloalkylsulfanil” refers to a saturated monovalent monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms bonded to a skeleton via sulfur atoms. Examples of monocyclic C3-C8-cycloalkylsulfanils include, but are not limited to, cyclopropylsulfanil, cyclobutylsulfanil, cyclopentylsulfanil, cyclohexylsulfanil, cycloheptylsulfanil, or cyclooctylsulfanil.

[0032] As used herein, the term “C1-C6-alkylsulfinyl” 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, 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, and hexylsulfinyl. Examples of C1-C6 alkyl sulfinyls include, but are not limited to, rufinyl, 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.

[0033] As used herein, the term "C1-C6-haloalkylsulfinyl" refers to a C1-C6 alkylsulfinyl in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0034] As used herein, the term “C3-C8-cycloalkylsulfinyl” refers to a saturated monovalent monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms bonded to a skeleton via an –S(=O)- group. Examples of monocyclic C3-C8-cycloalkylsulfinyl include, but are not limited to, cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, cycloheptylsulfinyl, or cyclooctylsulfinyl.

[0035] As used herein, the term “C1-C6-alkylsulfonyl” refers to a saturated linear or branched group of the 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, and 2-methylpentylsulfonyl. Examples include, but are not limited to, methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl, and 1-ethyl-2-methylpropylsulfonyl.

[0036] As used herein, the term "C1-C6-haloalkylsulfonyl" refers to a C1-C6-alkylsulfonyl group in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0037] As used herein, the term “C3-C8-cycloalkylsulfonyl” refers to a saturated monovalent monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7, or 8 carbon atoms bonded to the skeleton via an -S(=O)2- group. Examples of monocyclic C3-C8-cycloalkylsulfonyls include, but are not limited to, cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cycloheptylsulfonyl, or cyclooctylsulfonyl.

[0038] As used herein, the term "C1-C6-alkylcarbonyl" refers to a saturated linear or branched group of the formula (C1-C6-alkyl)-C(=O)-, where the term "C1-C6-alkyl" is defined herein.

[0039] As used herein, the term "C1-C6-haloalkylcarbonyl" refers to a C1-C6 alkylcarbonyl in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0040] As used herein, the term "C1-C6-alkoxycarbonyl" refers to a saturated linear or branched group of the formula (C1-C6-alkoxy)-C(=O)-, in which the term "C1-C6-alkoxy" is defined herein.

[0041] As used herein, the term "C1-C6-haloalkoxycarbonyl" refers to a C1-C6 alkoxycarbonyl in which one or more hydrogen atoms are substituted with one or more halogen atoms, which may be the same or different.

[0042] The term "C3-C" as used herein 12 The term "-carbocyclyl" refers to a saturated or partially unsaturated hydrocarbon ring system in which all ring members are carbon atoms, varying between 3 and 12. This ring system may be monocyclic or polycyclic (condensed, spiro, or bridging). C3-C 12 - The carbon ring is C3-C 12 -Cycloalkyl (monocyclic or bicyclic), C3-C 12 This includes, but is not limited to, cycloalkenyls (monocyclic or bicyclic), bicyclic systems containing aryls (e.g., phenyl) condensed onto monocyclic C3-C8-cycloalkyls (e.g., tetrahydronaphthalenyl, indanyl), bicyclic systems containing aryls (e.g., phenyl) condensed onto monocyclic C3-C8-cycloalkenyls (e.g., indenyl, dihydronaphthalenyl), and tricyclic systems containing cyclopropyls bonded to bicyclic systems containing aryls (e.g., phenyl) condensed onto C3-C8-cycloalkyls or C3-C8-cycloalkenyls via one carbon atom. 12 - The carbon ring can be bonded to the parent molecule via any carbon atom.

[0043] The term "C3-C" as used herein 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, bicyclo[2.2.1]hepta-2-enyl or bicyclo[2.2.2]octa-2-enyl.

[0044] The term "C6-C" used herein 14The term "aryl" refers to an aromatic hydrocarbon ring system in which all ring members are carbon atoms, varying between 6 and 14, preferably between 6 and 10. This ring system may be monocyclic or fused polycyclic (e.g., bicyclic or tricyclic). Examples of aryls include, but are not limited to, phenyl, azlenyl, and naphthyl.

[0045] As used herein, the term “3-membered–14-membered heterocyclyl” refers to saturated or partially unsaturated 3-membered, 4-membered, 5-membered, 6-membered, 7-membered, 8-membered, 9-membered, 10-membered, 11-membered, 12-membered, 13-membered, or 14-membered ring systems containing 1 to 4 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 directly adjacent. Heterocycles include, but are not limited to, 3-membered–7-membered monocyclic heterocycles and 8-membered–14-membered polycyclic (e.g., bicyclic or tricyclic) heterocycles. These 3-membered–14-membered heterocycles can be bonded to the parent molecule via any carbon or nitrogen atom contained within the heterocycle. Examples of saturated heterocycles include three-membered rings such as oxylanyl and azilidinyl, 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, and hexahydropyrimidinyl Examples of unsaturated heterocycles include, but are not limited to, six-membered rings such as piperazinyl, triazinanyl, hexahydrotriazinanyl, tetrahydropyranyl, dioxanyl, tetrahydrothiopyranyl, dithianyl, morpholinyl, 1,2-oxazinanyl, oxathianyl, and thiomorpholinyl, or seven-membered rings such as oxepanyl, azepanyl, 1,4-diazepanyl, and 1,4-oxazepanyl. Examples of unsaturated heterocycles include, but are not limited to, five-membered rings such as dihydrofuranyl, 1,3-dioxolyl, dihydrothienyl, pyrrolinyl, dihydroimidazolyl, dihydropyrazolyl, isoxazolinyl, dihydrooxazolyl, and dihydrothiazolyl, or six-membered rings such as pyranyl, thiopyranyl, thiadinyl, 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 it may consist of a monocyclic heterocycle fused to any of an aryl (e.g., phenyl), a C3-C8-cycloalkyl, a C3-C8-cycloalkenyl, or a monocyclic heterocycle (e.g., dihydrobenzofuranyl, dihydroisobenzofuranyl, indlinyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl). When two monocyclic heterocycles or one monocyclic heterocycle and one monocyclic heteroaryl containing a nitrogen atom are condensed, the nitrogen atom may be in the bridgehead position (e.g., [1,3]dioxolo[4,5-b]pyridinyl, 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydroimidazo[1,2-a]pyridinyl). The tricyclic heterocycle may consist of a monocyclic cycloalkyl bonded to a bicyclic heterocycle via a common atom.

[0046] As used herein, the terms “3-membered to 7-membered heterocyclyl” and “3-membered to 7-membered heterocyclyl ring” refer to saturated 3-membered, 4-membered, 5-membered, 6-membered, or 7-membered ring systems containing one or two heteroatoms independently selected from the group consisting of oxygen, nitrogen, and sulfur. Examples include oxylanil, azilidinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranil, 1,3-dioxolanil, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperadidinyl Examples of preferred 3- to 7-membered heterocyclyls include, but are not limited to, oxylanil, aziridinil, azetidinil, oxetanil, tetrahydrofuranil, 1,3-dioxolanil, pyrrolidinil, piperidinil, piperazinil, tetrahydropyranil, dioxanil, morpholinil, 1,2-oxazinanil, oxathianil, thiomorpholinil, oxepanil, azepanil, 1,4-diazepanil, and 1,4-oxazepanil.

[0047] As used herein, the term “5-membered to 14-membered heteroaryl” refers to an aromatic ring system containing 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen, and sulfur. If this ring system contains two or more oxygen atoms, they are not directly adjacent. Aromatic heterocycles include 5-membered or 6-membered monocyclic heteroaryls and 7-membered to 14-membered polycyclic (e.g., bicyclic or tricyclic) heteroaryls. These 5-membered to 14-membered heteroaryls can be bonded to the parent molecule via any carbon or nitrogen atom contained within the heterocycle.

[0048] As used herein, the term “5-membered or 6-membered heteroaryl” refers to a 5-membered or 6-membered aromatic monocyclic ring system containing one, two, three, or four 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, tetrazoyl, 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 tetradinyl.

[0049] As used herein, the term “7- to 14-membered heteroaryl” refers to a 7-, 8-, 9-, 10-, 11-, 12-, 13-, or 14-membered aromatic polycyclic (e.g., bicyclic or tricyclic) ring system containing 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 condensed with an aryl (e.g., phenyl) or a monocyclic heteroaryl. Examples of bicyclic heteroaryl compounds include, but are not limited to, nine-membered rings such as indolyl, indolidinyl, isoindolyl, benzimidazolyl, imidazopyridinyl, indazolyl, benzotriazolyl, prinyl, benzofuranil, benzothiophenyl, benzothiazolyl, benzoxazolyl, and benzisoxazolyl, or ten-membered rings such as quinolinyl, isoquinolinyl, sinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthilidinyl, pteridinal, and benzodioxynyl. In nine- or ten-membered bicyclic heteroaryls containing two fused five- or six-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, flu[2,3-d]isoxazolyl). Examples of tricyclic aromatic heterocycles include, but are not limited to, carbazoyl, acridinyl, and phenazinyl.

[0050] As used herein with respect to Y, the term 5- to 8-membered carbocyclyl condensed to a pyridine / pyridazine ring refers to a 5-, 6-, 7-, or 8-membered saturated or partially unsaturated ring condensed to a pyridine or pyridazine ring, respectively. As used herein with respect to Y, the term 5- to 8-membered heterocyclyl condensed to a pyridine / pyridazine ring refers to a 5-, 6-, 7-, or 8-membered saturated or partially unsaturated heterocycle containing one, two, or three heteroatoms or groups independently selected from N, O, S, SO, or SO2, condensed to a pyridine or pyridazine ring, respectively.Examples of the resulting bicyclic compounds include flo[3,2-b]pyridine, flo[3,2-c]pyridazine, thieno[2,3-b]pyridine, thieno[2,3-c]pyridazine, thieno[3,2-b]pyridine, thieno[3,2-c]pyridazine, pyrrolo[2,3-b]pyridine, 1H-pyrrolo[3,2-b]pyridine, 7H-pyrrolo[2,3-c]pyridazine, 5H-pyrrolo[3,2-c]pyridazine, thiazolo[5,4-b]pyridine, thiazolo[5,4-c]pyridazine, and oxazolo [5,4-b]pyridine, oxazolo[5,4-c]pyridazine, oxazolo[4,5-b]pyridine, oxazolo[4,5-c]pyridazine, thiazolo[4,5-b]pyridine, thiazolo[4,5-c]pyridazine, 1H-imidazo[4,5-b]pyridine, 5H-imidazo[4,5-c]pyridazine, 3H-imidazo[4,5-b]pyridine, 7H-imidazo[4,5-c]pyridazine, 1,5-naphthyridine, pyrido[3,2-c]pyridazine, pyrido[2,3- [c]pyridazine, pyridazino[3,4-c]pyridazine, pyridazino[4,3-c]pyridazine, quinoline, cinnoline, pyrido[3,2-d]pyrimidine, pyrimido[5,4-c]pyridazine, pyrido[3,4-c]pyridazine, pyrido[2,3-b]pyrazine, tetrahydroquinoline, tetrahydrocinnoline, dihydro-5H-cyclopenta[c]pyridazine, dihydro-5H-cyclopenta[c]pyridine, 2,3-dihydro-[1,4]dioxyno[2,3- Examples include, but are not limited to, [b]pyridine, 6,7-dihydro-[1,4]dioxyno[2,3-b]pyridazine, 7,8-dihydro-5H-pyrano[4,3-c]pyridazine, 5,6,7,8-tetrahydropyrido[3,2-c]pyridazine, 5,6,8,9-tetrahydrooxepino[4,5-c]pyridazine, 7,8-dihydro-6H-[1,4]dioxepino[2,3-c]pyridazine, and 1,2,3,4-tetrahydro-1,5-naphthyridine.

[0051] The term "C3-C" used herein 12 -Carbocyclyloxy", "C3-C8-cycloalkoxy", "C6-C 14The terms "-aryloxy", "5- to 14-membered heteroaryloxy", and "3- to 14-membered heterocyclyloxy" are defined herein as follows, where R is C3-C3, respectively. 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.

[0052] As used herein, the term “leaving group” should be understood to mean a group that is substituted from a compound in a substitution or elimination reaction, such as a halogen atom, a trifluoromethanesulfonate ("triflate") group, an alkoxy, a methanesulfonate, or a p-toluenesulfonate.

[0053] The phrase "as described herein" applies to variables A, Y, Q, T, and R. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 When referring to p, n, and m, broad definitions of the variables, as well as preferred, more preferred, and even more preferred ones, if any, are incorporated by reference.

[0054] Compounds resulting from combinations that violate the laws of nature and are therefore excluded by those skilled in the art based on their expertise are not included herein. For example, ring structures having three or more adjacent oxygen atoms are excluded.

[0055] The compounds of formula (I) may appropriately be in their free form, salt form, N-oxide form, or solvate form (e.g., hydrate).

[0056] Depending on the properties of the substituents, the compounds of formula (I) may exist in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers, or geometric isomers. Therefore, the present invention encompasses both pure stereoisomers and any mixture of these isomers. If a compound can exist in the form of two or more tautomers at equilibrium, a reference to the compound in the description of one tautomer is considered to include all tautomer forms.

[0057] Any of the compounds of the present invention may exist in one or more geometric isomeric forms, depending on the number of double bonds in the compound. Geometric isomers due to the properties of substituents on the double bonds or rings may exist in cis (=Z-) or trans (=E-) forms. Therefore, the present invention relates equally to all geometric isomers and all possible mixtures of any proportion.

[0058] Depending on the properties of the substituents, the compound of formula (I) may exist in the form of a free compound and / or a salt thereof, such as an active pesticide salt.

[0059] Pesticide active salts include acid addition salts of inorganic and organic acids, as well as salts of conventional bases. Examples of inorganic acids include hydrohalogens such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide, sulfuric acid, phosphoric acid, nitric acid, and acidic salts such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, alkanic 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 monounsaturated 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 (ferrous compounds having one or two sulfonic acid groups). Examples include aromatic radicals such as phenyl and naphthyl, alkylphosphonic acids (phosphonic acids having linear or branched alkyl radicals having 1 to 20 carbon atoms), and arylphosphonic acids or aryldiphosphonic acids (aromatic radicals such as phenyl and naphthyl having one or two phosphonic acid radicals) (the alkyl and aryl groups may have further substituents, such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.).

[0060] The compound of the present invention or the solvate of its salt is a stoichiometric composition of the compound and a solvent.

[0061] The compounds of the present invention may exist in polycrystalline and / or amorphous forms. Crystalline forms include non-solvated crystalline forms, solvates, and hydrates.

[0062] The present invention also relates to a process and intermediates for preparing the compound of formula (I).

[0063] The phrase "as described herein" refers to variables A and R. 1 , R 2 , R 3 , R 4 , R5 , R 6 , R 7 , R 8 When referring to T, Y, n, m, p, and Q, broad definitions of the variables, as well as preferred, more preferred, and even more preferred ones, if any, are incorporated by reference.

[0064] Therefore, the present invention relates to a compound of formula (1), T is oxygen (O) or sulfur (S), n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR 8 And, R 8 is hydrogen or halogen, R 1 These are hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, and -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 -S(=O)2R 12 -C(=O)N(R 13 )2, or -S(=O)2N(R 14 )2, R 10 , R 11 , and R 12 These are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl. R 13 and R 14 These are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl. R 2 and R 3 These are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, or C3-C8-cycloalkyl, or R 2 and R 3These, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclyl ring. R 4 and R 5 These are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl, or C3-C8-cycloalkyl, or R 4 and R 5 These, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclyl ring. or R 2 and R 4 These, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring or a 3- to 7-membered heterocyclyl ring. and R 3 and R 5 These are independently hydrogen or halogen, or R 2 and R 4 The formula ** -C(R 3 )=C(R 5 )- ## (In the ceremony ** is N(R 1 It is a connection point to ), ## is R 6 Forms the base of (which is a bonding point to), and R 3 and R 5 These are independently hydrogen or C1-C6-alkyl, R 6 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, C1-C3-alkoxy, or C1-C3-haloalkoxy, C1-C3-alkoxy and C1-C3-haloalkoxy are C3-C 12 -Carbocyclyl, C6-C 14 - Independently substituted with one substituent selected from the group consisting of aryls, 3- to 14-membered heterocyclines, and 5- to 14-membered heteroaryls, Said C3-C 12 -Carbocyclyl, C6-C 14 -aryls, 3- to 14-membered heterocyclines, and 5- to 14-membered heteroaryls are sequentially divided into 1 to 4 R 6S Substituting as desired with substituents, 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, and 3- to 14-membered heterocyclyloxy have 1 to 4 R 6S Substituting as desired with substituents, R 6SThese include halogens, cyano, isocyano, 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, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6- Alkyl sulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5-membered or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -N(R) 15 )2, -C(=O)R 16 , -C(=O)(OR 17 ), -C(=O)N(R 18 )2, -S(=O)2N(R 19 )2, -O-Si(C1-C6-alkyl)3, or -Si(C1-C6-alkyl)3, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkyls The ruhonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are further optionally substituted with 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-membered to 7-membered heterocyclyl. and The aforementioned C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5-membered or 6-membered heteroaryl, and 3- to 7-membered heterocyclyl are further optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl, or Two C1-C6-alkyl substituents bonded to the same carbon atom form a C3-C8-cycloalkyl ring. or 2 R 6SThe substituents, if desired, combine with the carbon atoms to which they are bonded to form a C3-C8-cycloalkyl ring. and R 15 is hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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-membered to 7-membered heterocyclyl groups. and The C3-C8-cycloalkyl group is further optionally substituted with 1 to 4 substituents independently selected from the group consisting of 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 16 , R 17 , R 18 , and R 19 These are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl, The C1-C6-alkyl or C1-C6-haloalkyl group may be further optionally substituted with 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-membered to 7-membered heterocyclyl groups. Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. p is 0, 1, 2, 3, or 4. R7 This includes halogens, cyano, nitro, hydroxyl, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2, or -S(=O)2N(R 24 )2, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, and C1-C6-haloalkylsulfonyl are optionally substituted with 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, and C3-C8-halocycloalkyl. C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. and R 20 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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, and C3-C8-halocycloalkyl groups. and The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 21 , R 22 , R 23 , and R 24 These are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. or Two substituents R 7 These, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring. 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 -Carbocyclyls, 3- to 14-membered heterocyclyls, and 5- to 14-membered heteroaryls include halogens, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-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-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 , -NR 26 C(=O)R 27-C(=O)N(R 28 )2, C(=S)R 29 -C(=S)N(R 30 )2, -C(=NR 31 )R 32 -C(=NOR 33 )R 34 , and -N(R 35 )1 to 5 Q independently selected from the group consisting of 2 S Substituting as desired with substituents, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkyls Ruffinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are optionally substituted with 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-membered to 7-membered heterocyclyl. The aforementioned C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, and 5- to 14-membered heteroaryl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyls may be optionally substituted with two substituents that, in order, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl. R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , and R 34 These are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, or C1-C6-alkoxy, The C1-C6-alkyl, C1-C6-haloalkyl, and C1-C6-alkoxy elements are optionally substituted with 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-membered to 7-membered heterocyclyl. and R 35is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, or C3-C8-cycloalkyl, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, and C2-C6-haloalkenyl are optionally substituted with 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-membered to 7-membered heterocyclyl. The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl groups. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl compounds are optionally substituted with two substituents that, in order, combine with the carbon atoms to which they are bonded to form a C3-C8-cycloalkyl group. The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0065] Preferably, the present invention relates to a compound of formula (1), T is oxygen (O) or sulfur (S), n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR 8 And, R8 is hydrogen, fluoro, chloro, methyl, or ethyl, R 1 This refers to hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, or -C(=O)R 10 And, R 10 It is a C1-C4 alkyl group, R 2 and R 3 These are independently hydrogen, fluoro, chloro, or C1-C4-alkyl, R 4 and R 5 These are independently hydrogen, halogen, C1-C4-alkyl, or C3-C6-cycloalkyl, or R 4 and R 5 These, together with the carbon atoms to which they are bonded, form a C3-C6-cycloalkyl ring. or R 2 and R 4 The formula ** -C(R 3 )=C(R 5 )- ## (In the ceremony ** is N(R 1 It is a connection point to ), ## is R 6 Forms the base of (which is a bonding point to), and R 3 and R 5 These are independently hydrogen, fluoro, or C1-C4-alkyl, R 6 C5-C 10 -Carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, 5- to 10-membered heteroaryl, C5-C 10 -Carbocyclyloxy, phenoxy, benzyloxy, 5- to 10-membered heteroaryloxy, 5- to 10-membered heterocyclyloxy, C1-C3-alkoxy, or C1-C3-haloalkoxy, C1-C3-alkoxy and C1-C3-haloalkoxy are C5-C 10 -Independently substituted with one substituent selected from the group consisting of carbocyryl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, and 5- to 10-membered heteroaryl, Said C5-C 10 -Carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, and 5- to 10-membered heteroaryl are sequentially 1 to 3 R 6S Substituting as desired with substituents, C5-C 10 -Carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, 5- to 10-membered heteroaryl, C5-C 10 -Carbocyclyloxy, phenoxy, naphthyloxy, 5- to 10-membered heteroaryloxy, and 5- to 10-membered heterocyclyloxy have 1 to 3 R 6S Substituting as desired with substituents, R 6S These are independently halogens, cyano, oxo, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, naphthyl, thienyl, pyrazolyl, imidazolyl, pyridinyl, pyrimidinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R 16 , or -C(=O)(OR 17 ) and The C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, and C2-C4-haloalkynyl are further optionally substituted with one or two substituents independently selected from the group consisting of cyano, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, -O-Si(C1-C4-alkyl)3, -Si(C1-C4-alkyl)3, and C3-C6-cycloalkyl. and The C3-C6-cycloalkyl, C3-C6-cycloalkenylphenyl, naphthyl, thienyl, pyrazolyl, imidazolyl, pyridinyl, pyrimidinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, and tetrahydropyranyl are further optionally substituted with one or two substituents independently selected from the group consisting of halogens, C1-C4-alkyl, C1-C4-haloalkyl, and C1-C6-alkoxycarbonyl. R 16 and R 17 These are independently C1-C4-alkyl groups. The aforementioned ring Y is either a pyridine ring or a pyridazine ring, and together with the formulas (II-a) to (II-aa):

[0066] [ka] [ka]

[0067] (In the formula, * This is a bonding site to the -OQ group, # is -N(R 1 It is a connection point to ), G stands for oxygen (O), sulfur (S), or NR 7L And, R 7L These are hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, or C3-C8-cycloalkyl. p is 0, 1, 2, 3, or 4. x 1 is either 1 or 2, x 2 is 0, 1, or 2, R 7A , R 7B , R 7C , R 7D , R 7E , R 7F , and R 7GThese are independently hydrogen, hydroxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, or C3-C8-cycloalkyl, 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 Two substituents R 7K These, together with the carbon atoms to which they are bonded, form a group that forms a C3-C8-cycloalkyl ring. Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indlinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxynyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thi Azolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, phlopyridinyl, thienothiophenyl, or thienothiazolyl, including phenyl, naphthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl Chromanil, dihydro-1,4-benzodioxynil, [1,3]dioxolo[4,5-b]pyridinil, tetrahydroquinolinil, dihydro-5H-cyclopenta[b]pyridinil, pyrrolyl, furanil, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranil, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinil, flupyridinil, thienothiophenyl, and thienothiazolyl are halo Gen, cyano, nitro, hydroxyl, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-haloalkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkoxy-C1-C4-alkyl, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C3-C6-cycloalkyl, oxetanyl, and -N(R 35)1 to 3 Q independently selected from the group consisting of 2 S Substituting as desired with substituents, The C3-C6-cycloalkyl group may optionally be substituted with one or two substituents independently selected from the group consisting of halogens, C1-C4-alkyl groups, and C1-C4-haloalkyl groups. and R 35 These are compounds that are independently hydrogen or C1-C4-alkyl. The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0068] Preferably, the present invention also includes a compound of formula (1), T is oxygen (O) or sulfur (S), n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR 8 And, R 8 is hydrogen or halogen, R 1 These are hydrogen, C1-C4-alkyl, and -C(=O)R 10 , -C(=O)(OR 11 ), or -C(=O)N(R 13 )2, R 10 , R 11 , and R 12 C1-C 64 -Alkyl, C3-C6-cycloalkyl, or C2-C4-alkenyl, R 2 and R 3 These are independently hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxycarbonyl, or C3-C6-cycloalkyl, or R 2 and R 3 These, together with the carbon atoms to which they are bonded, form a C3-C6-cycloalkyl ring. R 4and R 5 These are independently hydrogen, halogen, hydroxyl, C1-C4-alkyl, or C1-C4-haloalkyl, or R 4 and R 5 These, together with the carbon atoms to which they are bonded, form a C3-C6-cycloalkyl ring. or R 2 and R 4 These, together with the carbon atoms to which they are bonded, form a C3-C6-cycloalkyl ring. and R 3 and R 5 These are independently hydrogen or halogen, or R 2 and R 4 The formula ** -C(R 3 )=C(R 5 )- ## (In the ceremony ** is N(R 1 It is a connection point to ), ## is R 6 Forms the base of (which is a bonding point to), and R 3 and R 5 These are independently hydrogen or C1-C4-alkyl, R 6 C7-C 12 -Carbocyclyl, phenyl, naphthyl, 7-12 member heterocyclyl, 5-12 member heteroaryl, C7-C 12 -Carbocyclyloxy, phenoxy, naphthoxy, 7- to 12-membered heteroaryloxy, 7- to 12-membered heterocyclyloxy, C1-C3-alkoxy, or C1-C3-haloalkoxy, C1-C3-alkoxy and C1-C3-haloalkoxy are C7-C 12-Independently substituted with one substituent selected from the group consisting of carbocyrills, phenyls, naphthyls, 5- to 12-membered heterocyclines, and 5- to 12-membered heteroaryls, Said C7-C 12 -Carbocyclyl, phenyl, naphthyl, 5- to 12-membered heterocyclyl, and 5- to 12-membered heteroaryl are sequentially divided into 1 to 3 R 6S Substituting as desired with substituents, C7-C 12 -Carbocyclyl, phenyl, naphthyl, 7-12 member heterocyclyl, 5-12 member heteroaryl, C7-C 12 -Carbocyclyloxy, phenoxy, naphthoxy, 7- to 12-membered heteroaryloxy, 7- to 12-membered heterocyclyloxy have 1 to 3 R 6S Substituting as desired with substituents, R 6S This includes halogens, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-alkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, C2-C4-haloalkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, naphthyl, 5-membered or 6-membered heteroaryl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R 16 , or -C(=O)(OR 17 ) and The aforementioned C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyl, C2-C4-haloalkenyl, C2-C4-alkynyl, and C2-C4-haloalkynyl are further optionally substituted with one or two substituents independently selected from the group consisting of cyano, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, -O-Si(C1-C4-alkyl)3, -Si(C1-C4-alkyl)3, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and 3-membered to 7-membered heterocyclyl. and The C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, naphthyl, 5-membered or 6-membered heteroaryl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, and tetrahydropyranyl are further optionally substituted with one or two substituents independently selected from the group consisting of halogens, C1-C4-alkyl, C1-C4-haloalkyl, and C1-C4-alkoxycarbonyl. and R 16 and R 17 These are independently C1-C4-alkyl groups. The aforementioned ring Y, together with either a pyridine ring or a pyridazine ring, is represented by formulas (II-a) to (II-v):

[0069] [ka] [ka]

[0070] * This is a bonding site to the -OQ group, # is -N(R 1 It is a connection point to ), p is 0, 1, 2, 3, or 4. x 1 is either 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 These are independently hydrogen, hydroxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy. R 7H is hydrogen, C1-C4-alkyl, or C1-C4-haloalkyl, R7K is methylidene, halomethylidene, halogen, hydroxyl, oxo, C1-C4-alkyl, C1-C6-haloalkyl, or C3-C6-cycloalkyl, or Two substituents R 7K These, together with the carbon atoms to which they are bonded, form a group that forms a C3-C8-cycloalkyl ring. Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indlinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxynyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, phlopyridinyl, thienothiophenyl, or thienothiazolyl, Phenyl, naphthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxynyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl Benzothiazolyl, benzoxazolyl, quinolinyl, phlopyridinyl, thienothiophenyl, and thienothiazolyl are halogens, 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-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C6-cycloalkyl, oxetanyl, and -N(R 43 )1 to 3 Q independently selected from the group consisting of 2 S Substituting as desired with substituents, The C3-C6-cycloalkyl and oxetanyl are optionally substituted with one or two substituents independently selected from the group consisting of halogens, C1-C4-alkyl and C1-C4-haloalkyl groups. R 43 These are compounds consisting of hydrogen and C1-C6-alkyl groups. The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0071] More preferably, the present invention also relates to a compound of formula (1), T is oxygen (O) or sulfur (S), n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR 8 And, R 8 is hydrogen or methyl, R 1 This refers to hydrogen, hydroxyl, C1-C4-alkyl, C1-C4-alkoxy, or -C(=O)R 10 And, R 10 is methyl or ethyl, R 2 and R 3 It is hydrogen, R 4 and R 5 These are independently hydrogen, fluoro, methyl, or ethyl, or R 2 and R 4 The formula ** -C(R 3 )=C(R 5 )- ## (In the ceremony ** is N(R 1 It is a connection point to ), ## is R 6 Forms the base of (which is a bonding point to), and R 3 and R 5 It is hydrogen, R 6 These are tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanil, isochromanil, thiochromanil, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, furanil, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, indolyl, benzothiazolyl, phenoxy, or benzyloxy, Tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, indolyl, benzothiazolyl, phenoxy, and benzyloxy contain 1-3 R 6S Substituting as desired with substituents, R 6S These are independently halogens, cyano, oxo C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C5-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, or -C(=O)R 16 And, R 16 It is a C1-C4 alkyl group, The aforementioned ring Y, together with either a pyridine ring or a pyridazine ring, is represented by formulas (II-a), (II-b), (II-g), (II-h), (II-i), (II-r), (II-s), (II-u), or (II-v):

[0072] [ka]

[0073] (In the formula, * This is a bonding site to the -OQ group, # is -N(R 1 It is a connection point to ), p is 0, 1, or 2. x 1 is either 1 or 2, x 2 is 0, 1, or 2, G stands for oxygen (O), or NR.7L And, R 7L It is hydrogen, R 7A It is hydrogen, R 7B is hydrogen, fluoro, methyl, or methoxy, R 7C is hydrogen, fluoro, methyl, or methoxy, R 7D It is hydrogen, R 7E It is hydrogen, R 7F is hydrogen, and R 7K (It forms a hydroxyl or methyl group) Q is phenyl, pyridinyl, or pyrimidinyl, Phenyl, pyridinyl, and pyrimidinyl are each independently selected from the group consisting of halogens, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, cyclopropyl, and cyclobutyl, with one or two Q S Compounds that are optionally substituted by substituents, The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0074] Similarly, more preferably, the present invention relates to a compound of formula (I), T is oxygen (O) or sulfur (S), n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR 8 And, R 8 It is hydrogen, R 1 is hydrogen or -C(=O)R 10 And, R 10 It is a C1-C4 alkyl group, R 2 and R3 These are independently hydrogen, fluoromethyl, or ethyl. R 4 and R 5 These are independently hydrogen, fluoro, methyl, or ethyl, or R 4 and R 5 These, together with the carbon atoms to which they are bonded, form a cyclopropyl ring. or R 2 and R 4 The formula ** -C(R 3 )=C(R 5 )- ## (In the ceremony ** is N(R 1 It is a connection point to ), ## is R 6 Forms the base of (which is a bonding point to), and R 3 and R 5 It is independently hydrogen, R 6 This is tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanil, isochromanil, thiochromanil, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, furanil, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, benzothiazolyl, phenyloxy, or benzyloxy, Tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanil, isochromanil, thiochromanil, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, furanil, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, benzothiazolyl, phenyloxy, and benzyloxy contain 1-3 R 6S Substituting as desired with substituents, R 6SThese are independently halogens, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, or -C(=O)R 16 And, R 16 It is a C1-C4 alkyl group, The aforementioned ring Y, together with either a pyridine ring or a pyridazine ring, is represented by formulas (II-a), (II--b), (II--g), (II--h), (II---r), (II--s), (II--u), or (II--v):

[0075] [ka]

[0076] (In the formula, * This is a bonding site to the -OQ group, # is -N(R 1 It is a connection point to ), p is 0, 1, or 2. x 1 is either 1 or 2, x 2 is 0, 1, or 2, R 7A is hydrogen or C1-C4-alkyl, R 7B These are hydrogen, fluoro, C1-C4-alkyl, or C1-C4-alkoxy, R 7C These are hydrogen, fluoro, C1-C4-alkyl, or C1-C4-alkoxy, R 7D It is hydrogen, R 7E It is hydrogen, R 7FIt is hydrogen, R 7K It forms a group that is hydroxyl, C1-C4-alkyl, or C1-C4-alkoxy, Q is phenyl or pyridinyl, Phenyl and pyridinyl are each independently selected from the group consisting of halogens, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, and cyclobutyl, with one or two Q S Compounds that are optionally substituted by substituents, The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0077] More preferably, T is oxygen (O).

[0078] More preferably, n is 1 and m is 1.

[0079] Preferably, R 1 C(=O)R 10 , or -C(=O)(OR 11 ) and R 10 and R 11 These are independently C1-C6-alkyl or C2-C6-alkenyl.

[0080] Comfortable, R 1 is hydrogen or -C(=O)R 10 And R 10 It is a C1-C6 alkyl group.

[0081] Furthermore, R 1 It is hydrogen.

[0082] Appropriate R 1 A non-restrictive example is the column "R" in Table 1. 1 R disclosed in "1 It includes one of the bases.

[0083] Preferably, R 2 and R 3 is independently hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxycarbonyl, or C3-C6-cycloalkyl, or R 2 and R 3 These, together with the carbon atoms to which they are bonded, form a C3-C6 cycloalkyl ring.

[0084] Comfortable, R 2 and R 3 is independently hydrogen or C1-C4 alkyl, or R 2 and R 3 These, together with the carbon atoms to which they are bonded, form a cyclopropyl ring.

[0085] Preferably, R 4 and R 5 is independently hydrogen, halogen, hydroxyl, C1-C4-alkyl, or C1-C4-haloalkyl, or R 4 and R 5 These, together with the carbon atoms to which they are bonded, form a C3-C6 cycloalkyl ring.

[0086] Comfortable, R 4 and R 5 is independently hydrogen or fluoro, or R 4 and R 5 These atoms, together with the carbon atoms to which they are bonded, form a cyclopropyl ring.

[0087] Preferably, R 2 and R 4 It forms a cyclopropyl ring, and R 3 and R 5 These are independently hydrogen or halogen.

[0088] Comfortable, R1 is hydrogen, R 2 and R 3 R is independently hydrogen or C1-C4-alkyl, 4 and R 5 is independently hydrogen or fluoro, or R 4 and R 5 These, together with the carbon atoms to which they are bonded, form a cyclopropyl ring.

[0089] More preferably, n is 0 or 1, m is 0 or 1, and R 2 and R 3 is hydrogen, R 4 and R 5 These are independently hydrogen, fluoro, methyl, or ethyl, or R 4 and R 5 These, together with the carbon atoms to which they are bonded, form a cyclopropyl ring. or R 2 and R 4 The formula ** -C(R 3 )=C(R 5 )- ## (In the formula, ** is N(R 1 It is a connection point to ), ## is R 6 It forms the base of (which is a bonding point to).

[0090] Preferably, R 6 is one C6-C 14 - C7-C substituted with aryl 12 -carbocycle, C6-C 14 -aryl, 5- to 12-membered heterocyclyl, 5- to 12-membered heteroaryl, C6-C 14 -Aryloxy and C1-C3-alkoxy, Said C6-C 14 -The aryl group may have 1 to 3 substituents R as desired. 6S Replaced by, C7-C 12 -carbocycle, C6-C14 -aryl, 5- to 12-membered heterocyclyl, 5- to 12-membered heteroaryl, and C6-C 14 - Aryloxy has 1 to 3 substituents R 6S Replaced as desired, R 6S These include halogens, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R 16 , and -C(=O)(OR 17 Independently selected from the group consisting of, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl are cyano, hydroxyl, C1-C4-alkoxy, C1-C4-haloalkoxy, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, and 3-membered to 7-membered heteroalkyl They are further optionally substituted with one or two substituents independently selected from the group consisting of lyls, and the C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, and tetrahydropyranyl are further optionally substituted with one or two substituents independently selected from the group consisting of halogens, C1-C6-alkyl, C1-C6-haloalkyl, and C1-C6-alkoxycarbonyl, and R 16 It is C1-C6-alkyl, and R 17 It is hydrogen or a C1-C6 alkyl group.

[0091] Comfortable, R 6These include phenyl, naphthyl, indanyl, tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanil, isochromanil, thiochromanil, isothiochromanil, dihydro-1,4-benzodiol Xynyl, tetrahydrobenzothiophenyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, dihydro-4H-cyclopenta[b]thiophenyl, dihydro-4H-cyclopenta[d]thiazolyl, tetrahydropyrazolo[1,5-a]pyridinyl, tetrahydro Dro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl These are indazolyl, benzofuranil, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]xazolyl, furo[2,3-d]isoxazolyl, or thieno[2,3-d]isothiazolyl. Phenyl, naphthyl, indanyl, tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro-1,4-ben Zodioxynyl, tetrahydrobenzothiophenyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, dihydro-4H-cyclopenta[b]thiophenyl, dihydro-4H-cyclopenta[d]thiazolyl, tetrahydropyrazolo[1,5-a]pyridinyl Nyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indri Lu, benzimidazolyl, indazolyl, benzofuranil, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, flo[2,3-d]isoxazolyl, and thieno[2,3-d]Isothiazolyl is a halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, -C(=O)R, 16 , and -C(=O)(OR 17 ) One or two substituents R independently selected from the group consisting of ) 6S The C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, and pyridinyl are optionally substituted with one or two substituents independently selected from the group consisting of fluoro, chloro, C1-C4-alkyl, and C1-C4-haloalkyl, and R 16 is C1-C4-alkyl, and R 17 It is hydrogen or a C1-C4 alkyl group.

[0092] Furthermore, R 6 This is tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanil, isochromanil, thiochromanil, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, furanil, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, benzothiazolyl, phenyloxy, or benzyloxy, Tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanil, isochromanil, thiochromanil, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, furanil, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, benzothiazolyl, phenyloxy, or benzyloxy may have 1 or 2 R 6S Substituting as desired with substituents, R 6SThese are independently halogens, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, or -C(=O)R 16 and R 16 It is a C1-C4 alkyl group.

[0093] In a more preferred embodiment, R 6 teeth,

[0094] [ka] or [ka] And,

[0095] During the ceremony, §1 is C(R 4 R 5 )m, is a connection point, R 6S1 and R 6S2 These are independently hydrogen or R 6S And, R 6S These are halogens, cyanos, C1-C4-alkyls, C1-C4-haloalkyls, C1-C4-alkoxys, C1-C6-haloalkoxys, C1-C6-alkoxycarbonyls, C1-C6-alkylcarbonyls, C2-C6-alkenyls, C2-C6-alkynyls, C3-C6-cycloalkyls, and pyrazolyls. The C3-C6-cycloalkyl and pyrazolyl groups are optionally substituted with one or two substituents independently selected from the group consisting of halogens and C1-C4-alkyl groups. R 6S1 and R 6S2 At least one of them is different from hydrogen.

[0096] Preferably, n is 0, m is 0, and R 6 These include naphthyl, indanyl, tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, dihydrobenzofuranyl, dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro- 1,4-Benzodioxynyl, tetrahydrobenzothiophenyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, dihydro-4H-cyclopenta[b]thiophenyl, dihydro-4H-cyclopenta[d] Thiazolyl, tetrahydropyrazolo[1,5-a]pyridinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophene These are nyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl, or thieno[2,3-d]isothiazolyl. Naphthyl, indanyl, tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, dihydrobenzofuranyl, dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro-1,4- Benzodioxynyl, tetrahydrobenzothiophenyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranyl, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, dihydro-4H-cyclopenta[b]thiophenyl, dihydro-4H-cyclopenta[d]thiazolyl, Tetrahydropyrazolo[1,5-a]pyridinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothia Zolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl, and thieno[2,3-d]isothiazolyl have one or two substituents R 6S Replaced by as desired, R 6SThese include halogens, cyano, oxo, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, and -C(=O)R 16 , and -C(=O)(OR 17 Independently selected from the group consisting of, The C3-C6-cycloalkyl, phenyl, pyrazolyl, imidazolyl, and pyridinyl compounds may optionally be further substituted with one or two substituents independently selected from the group consisting of fluoro, chloro, C1-C4-alkyl, and C1-C4-haloalkyl compounds. and R 16 It is a C1-C4 alkyl group, R 17 It is either hydrogen or a C1-C4 alkyl group.

[0097] comfortable, n is 0, m is 0, and R 6 These are tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, dihydrobenzofuranil, chromanil, isochromanil, thiochromanil, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, indolyl, or benzothiazolyl, Tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, dihydrobenzofuranyl, chromanyl, isochromanyl, thiochromanyl, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, indolyl, and benzothiazolyl contain 1-3 R 6S Substituting as desired with substituents, R 6SThese include halogens, cyano, oxo, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C5-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, or -C(=O)R 16 And, R 16 It is a C1-C4 alkyl group.

[0098] Preferably, n is 0 or 1, m is 1, and R 6 is phenyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, phenyloxy, or benzyloxy, Phenyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, phenyloxy, or benzyloxy may have one or two substituents R 6S Replaced as desired, R 6S These are independently halogens, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, or -C(=O)R 16 And, R 16 It is a C1-C4 alkyl group.

[0099] comfortable, n is 0 or 1, m is 1, and R 6 It is phenyl, Phenyl has one or two substituents R 6S Replaced as desired, R 6SThese are independently halogens, C1-C4-alkyls, difluoromethyls, trifluoromethyls, C1-C4-alkoxys, difluoromethoxys, trifluoromethoxys, C2-C4-alkenyls, C2-C4-alkynyls, or C3-C6-cycloalkyls.

[0100] A suitable non-restrictive example of the following chain is:

[0101] [ka]

[0102] It includes one of the following chains

[0103] [ka]

[0104] Table 1

[0105] [ka]

[0106] This will be disclosed in the column.

[0107] Preferably, p is 0, 1, 2, or 3. More preferably, p is 0, 1, or 2.

[0108] Preferably, x 1 is 1 or 2 and x 2 x is 0, 1, or 2. More preferably, x 1 is 1 or 2 and x 2 It is 0, 1, or 2.

[0109] Preferably, R 7A , R 7B , R 7C , R 7D , R 7E , R 7F , and R 7GR is independently hydrogen, hydroxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, or C1-C4-haloalkoxy, 7H is hydrogen, C1-C4-alkyl, or C1-C4-haloalkyl, and R 7K These are halogens, hydroxyls, oxo, C1-C4-alkyl, C1-C6-haloalkyl, or C3-C6-cycloalkyl.

[0110] Comfortable, R 7A R is hydrogen or C1-C4-alkyl, 7B R is hydrogen, fluoro, C1-C4-alkyl, or C1-C4-alkoxy, 7C R is hydrogen, fluoro, C1-C4-alkyl, or C1-C4-alkoxy, 7D is hydrogen, R 7E is hydrogen, R 7F is hydrogen, and R 7K These are hydroxyl, C1-C4-alkyl, or C1-C4-alkoxy.

[0111] Preferably, ring Y forms a bicyclic heterocycline or bicyclic heteroaryl with a pyridine ring or pyridazine ring, respectively, and the bicyclic heterocycline and bicyclic heteroaryl contain 3 to 6 double bonds and 1 to 4 heteroatoms or groups selected from N, O, S, SO, and SO2.

[0112] More preferably, the ring Y, together with the pyridine ring or pyridazine ring, is flu[3,2-b]pyridine, flu[3,2-c]pyridazine, thieno[2,3-b]pyridine, thieno[2,3-c]pyridazine, thieno[3,2-b]pyridine, thieno[3,2-c]pyridazine, thiazolo[5,4-b]pyridine, thiazolo[5,4-c]pyridazine, oxazolo[5,4-b]pyridazine Zin, oxazolo[5,4-c]pyridazine, oxazolo[4,5-b]pyridine, oxazolo[4,5-c]pyridazine, thiazolo[4,5-b]pyridine, thiazolo[4,5-c]pyridazine, 1H-imidazo[4,5-b]pyridine, 5H-imidazo[4,5-c]pyridazine, 3H-imidazo[4,5-b]pyridine, 7H-imidazo[4,5-c]pyridazine, 1,5-naphthyridine, Pyrido[3,2-c]pyridazine, quinoline, cinnoline, pyrido[3,2-d]pyrimidine, pyrimido[5,4-c]pyridazine, pyrido[3,4-c]pyridazine, pyrido[2,3-b]pyrazine, tetrahydroquinoline, tetrahydrocinnoline, dihydro-5H-cyclopenta[c]pyridazine, dihydro-5H-cyclopenta[c]pyridine, 2,3-dihydro-[1,4]dioxyno They form [2,3-b]pyridine, 6,7-dihydro-[1,4]dioxyno[2,3-b]pyridazine, 7,8-dihydro-5H-pyrano[4,3-c]pyridazine, 5,6,7,8-tetrahydropyrido[3,2-c]pyridazine, 5,6,8,9-tetrahydrooxepino[4,5-c]pyridazine, or 7,8-dihydro-6H-[1,4]dioxepino[2,3-c]pyridazine.

[0113] More preferably, the ring Y, together with the pyridine ring or pyridazine ring, is in the form of formula (II-a), formula (II--b), formula (II--g), formula (II--h), formula (II---r), formula (II--s), formula (II--u), or formula (II--v):

[0114] [ka]

[0115] (In the formula, * This is a bonding site to the -OQ group, # is -N(R 1 It is a connection point to ), p is 0, 1, or 2. x 1 is either 1 or 2, x 2 is 0, 1, or 2, R 7A is hydrogen or C1-C4-alkyl, R 7B These are hydrogen, fluoro, C1-C4-alkyl, or C1-C4-alkoxy, R 7C These are hydrogen, fluoro, C1-C4-alkyl, or C1-C4-alkoxy, R 7D It is hydrogen, R 7E It is hydrogen, R 7F It is hydrogen, R 7K It forms a group that is hydroxyl, C1-C4-alkyl, or C1-C4-alkoxy.

[0116] Similarly, and more preferably, the ring Y, together with the pyridine ring or pyridazine ring, forms a group of formula (II-a), formula (II-b), formula (II-g), formula (II-h), formula (II-r), formula (II-s), formula (II-u), or formula (II-v), The aforementioned ring Y, together with either a pyridine ring or a pyridazine ring, is represented by formulas (II-a), (II-b), (II-g), (II-h), (II-i), (II-r), (II-s), (II-u), or (II-v):

[0117] [ka]

[0118] (In the formula, *This is a bonding site to the -OQ group, # is -N(R 1 It is a connection point to ), p is 0, 1, or 2. x 1 is either 1 or 2, x 2 is 0, 1, or 2, G stands for oxygen (O), or NR. 7L And, R 7L It is hydrogen, R 7A It is hydrogen, R 7B is hydrogen, fluoro, methyl, or methoxy, R 7C is hydrogen, fluoro, methyl, or methoxy, R 7D It is hydrogen, R 7E It is hydrogen, R 7F It is hydrogen. and R 7K It forms a group (which is hydroxyl or methyl).

[0119] Preferably, Q is 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, dihydroisobenzofuranyl, indlinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxynyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydro Quinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanil, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranil, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thiophenyl, or thieno[2,3-d]thiazolyl, which are preferred In addition, 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, dihydroisobenzofuranyl, indlinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxynyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanil, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranil, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thiophenyl, and thieno[2,3-d]thiazolyl have 1 to 4 substituents Q S Replaced as desired,

[0120] Q SThese are independently halogens, 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-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C6-cycloalkyl, oxetanyl, or -N(R) 43 )2 wherein the C3-C6-cycloalkyl and oxetanyl are optionally substituted with one or two substituents independently selected from the group consisting of halogens, C1-C4-alkyl and C1-C4-haloalkyl, and R 43 It is hydrogen or a C1-C6 alkyl group.

[0121] 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 have 1 to 3 substituents Q S Replaced as desired,

[0122] Q S The substituents are independently halogen, cyano, nitro, formyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkynyl, or C3-C6-cycloalkyl, wherein the C3-C6-cycloalkyl and oxetanyl substituents are optionally substituted in sequence with one or two substituents independently selected from the group consisting of fluoro or methyl.

[0123] More preferably, Q is phenyl or pyridinyl, and phenyl or pyridinyl is one or two Qs independently selected from the group consisting of halogens, cyano, C1-C4-alkyl, difluoromethyl, trifluoromethyl, C1-C4-alkoxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, or cyclobutyl. S Substitutions are optionally used.

[0124] More specifically, Q is

[0125] [ka] or [ka]

[0126] (In the formula, §2 is a bond to the oxygen atom, Q S1 is hydrogen or fluoro, Q S2 These are hydrogen, chloro, bromo, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, or cyclobutyl, Q S1 and Q S2 At least one of them is different from hydrogen.

[0127] A non-restrictive example of a suitable Q would include any of the Q elements listed in the "Q" column of Table 1.

[0128] m, n, p, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8The above specific definitions of A, T, Y, and Q (broad definitions as well as preferred, more preferred, and even more preferred definitions) can be combined in various ways. Thus, these combinations of definitions provide subclasses of compounds according to the present invention, such as those disclosed below.

[0129] The present invention also relates to any compound of formula (I) disclosed in Table 1.

[0130] Compounds resulting from combinations that violate the laws of nature and are therefore excluded by those skilled in the art based on their expertise are not included herein. For example, ring structures having three or more adjacent oxygen atoms are excluded.

[0131] The compounds of formula (I) may appropriately be in their free form, salt form, N-oxide form, or solvate form (e.g., hydrate).

[0132] Depending on the properties of the substituents, the compounds of formula (I) may exist in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers, or geometric isomers. Therefore, the present invention encompasses both pure stereoisomers and any mixture of these isomers. If a compound can exist in the form of two or more tautomers at equilibrium, a reference to the compound in the description of one tautomer is considered to include all tautomer forms.

[0133] Any of the compounds of the present invention may exist in one or more geometric isomeric forms, depending on the number of double bonds in the compound. Geometric isomers due to the properties of substituents on the double bonds or rings may exist in cis (=Z-) or trans (=E-) forms. Therefore, the present invention relates equally to all geometric isomers and all possible mixtures of any proportion.

[0134] Depending on the properties of the substituents, the compound of formula (I) may exist in the form of a free compound and / or a salt thereof, such as an active pesticide salt.

[0135] Pesticide active salts include acid addition salts of inorganic and organic acids, as well as salts of conventional bases. Examples of inorganic acids include hydrohalogens such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide, sulfuric acid, phosphoric acid, nitric acid, and acidic salts such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, alkanic 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 monounsaturated 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 (ferrous compounds having one or two sulfonic acid groups). Examples include aromatic radicals such as phenyl and naphthyl, alkylphosphonic acids (phosphonic acids having linear or branched alkyl radicals having 1 to 20 carbon atoms), and arylphosphonic acids or aryldiphosphonic acids (aromatic radicals such as phenyl and naphthyl having one or two phosphonic acid radicals) (the alkyl and aryl groups may have further substituents, such as p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.).

[0136] The compound of the present invention or the solvate of its salt is a stoichiometric composition of the compound and a solvent.

[0137] The compounds of the present invention may exist in polycrystalline and / or amorphous forms. Crystalline forms include non-solvated crystalline forms, solvates, and hydrates.

[0138] The compounds of formula (I) can be used as fungicides (for controlling plant pathogenic fungi), particularly in methods for controlling plant pathogenic fungi that include the step of applying one or more compounds of formula (I) to plants.

[0139] Process for preparing the compound and intermediate of formula (I) The present invention relates to a process for preparing compounds of formula (I) and their intermediates. Unless otherwise indicated, A, R are radicals. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 T, Y, n, m, p, and Q have the meanings given above for the compound of formula (I). These definitions apply not only to the final product of formula (I) but also to all intermediates.

[0140] The compounds of formulas (Ia) to (Ib) are subsets of formula (I). The compounds of formulas (Ia-1) to (Ia-3) are various subsets of formula (Ia). All substituents in formulas (Ia) to (Ib) and (Ia-1) to (Ia-3) are as defined above for formula (I), unless otherwise specified.

[0141] Compounds of general formula (I) can be prepared by various routes, as well as by known processes (see, for example, the references therein). A non-limiting example of a suitable process is described herein.

[0142] The compound of formula (I) may be obtained directly by carrying out process A, B, or C, or by the conversion or derivatization of another compound of formula (I) prepared according to the processes described herein. For example, the compound of formula (I) can be converted to another compound of formula (I) by substituting one or more substituents of the starting compound of formula (I) with other substituents.

[0143] The processes described herein can be adequately carried out using one or more inert organic solvents that are conventional for the reactions under consideration. Suitable inert organic solvents may be selected from: 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 ethyl ether, etc.) Any of the following: sopropyl ketones and methyl isobutyl ketones), esters (e.g., methyl acetate, ethyl acetate, or butyl acetate), alcohols (e.g., methanol, ethanol, propanol, isopropanol, butanol, tert-butanol), nitriles (e.g., acetonitrile, propionitrile, n- or i-butyronitrile, or benzonitrile), amides (e.g., N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone, or hexamethylphosphate triamide), sulfoxides (e.g., dimethyl sulfoxide) or sulfones (e.g., sulfolane), ureas (e.g., 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinene), or mixtures thereof.

[0144] Some of the processes described herein require, or may be used as appropriate, one or more inorganic or organic bases that are 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 metals, alkali metals, 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 alkalis include, but are not limited to, alkali metal phosphates (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 colidine).

[0145] Some of the processes described herein may be carried out, if appropriate, in the presence of a transition metal catalyst, such as a metal (e.g., copper or palladium) salt or complex, and, if appropriate, a ligand.

[0146] Suitable copper salts or complexes and their hydrates 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(II) 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, and tetrakis(acetonitrile)-copper(I) tetrafluoroborate.

[0147] By separately adding the following copper salts to the reaction with ligands or salts, a suitable copper complex can be added to the reaction mixture in situ (in It is also possible to produce them 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, quinoline-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-dimethyl C-1,10-phenanthroline, N,N'-bis[(E)-pyridine-2-ylmethylidene]cyclohexane-1,2-diamine, N-[(E)-phenylmethylidene], N-[(E)-phenylmethylidene]-cyclohexaneamine, 1,1,1-tris(hydroxymethyl)ethane, ethylene glycol, 2,2,6,6-tetramethylheptan-3,5-dione, 2-(2,2-dimethylpropanoyl)cyclohexanone, acetylacetone, dibenzoylmethane, 2-(2-methylpropanoyl)cyclohexanone, biphenyl-2-yl(di-tert-butyl)phosphan, ethylenebis-(diphenylphosphine), N,N-diethylsalicylamide, 2-hydroxybenzaldehyde oxime, oxo[(2,4,6-trimethylphenyl)amino]acetic acid, or 1H-pyrrole-2-carboxylic acid.

[0148] Suitable palladium salts or complexes include, but are not limited to, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium(O), bis(dibenzylideneacetone)palladium(O), tris(dibenzylideneacetone)dipalladium(O), 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).

[0149] It is also possible to generate palladium complexes in the reaction mixture by separately adding the following palladium salts to the reaction with ligands or salts: triethylphosphine, tri-tert-butylphosphine, tri-tert-butylphosphonium tetrafluoroborate, tricyclohexylphosphine, 2-(dicyclohexylphosphine)biphenyl, 2-(di-tert-butylphosphine)biphenyl, 2-(dicyclohexylphosphine)-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, trif Phenylphosphine, tris-(o-tolyl)phosphine, sodium 3-(diphenylphosphino)benzenesulfonate, tris-(2-methoxyphenyl)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-(disy Chlohexylphosphino)-2'-(N,N-dimethylamino)-biphenyl, 1,1'-bis(diphenylphosphino)-ferrocene, (R)-(-)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, tris-(2,4-tert-butylphenyl) phosphate, di(1-adamantyl)-2-morpholinophenylphosphine, or 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride.

[0150] Suitable catalysts and / or ligands can 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 the references listed).

[0151] 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; Science (2016) 352, 6291, 1304; Org. Lett. 2016, 18, 4012, J. Org. Chem 2016, 81, 6898; J. Am. Chem. Soc. 2016, 138, 12715, J. Am. Chem. Soc. 2016, 138, 13862; J. Am. Chem. Soc. 2016, 138, 8034; J. Org. Chem. 2016, 81, 12525, J. Org. Chem. 2015, 80, 7642). The process is then carried out in the presence of an Ir compound, a photosensitizer such as a Ru complex or organic dye, and a metal catalyst such as a Ni complex. The reaction can be carried out in the presence of a ligand, and optionally a base, and under the irradiation of blue or white light.

[0152] 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 (dFCF3ppy = 2-(2,4-difluorophenyl)pyridine), fac-Ir(ppy)3, (Ir[diF(5-Me)ppy]2(tetraMePhen) Examples include, but are not limited to, iridium(Ir)(III) photocatalysts such as 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, organic dyes such as 9-mesityl-10-acridinium, salts such as perchlorates or tetrafluoroborate, or 2,4,5,6-tetra-9H-carbazole-9-yl-1,3-benzenedicarbonitride, 9-fluorenone, and 9,10-phenanthrenequinone.

[0153] 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 hydrate form, or as a dimethoxyethane complex), nickel(II) acetylacetonate, and nickel(II) nitrate hexahydrate. These nickel catalysts can be used in combination with bipyridine ligands such as 2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 4,4'-dimethoxy-2,2'-bipyridine, or phenanthrolines such as 1,10-phenanthroline, 4,7-dimethyl-1,10-phenanthroline, or 4,7-dimethoxy-1,10-phenanthroline, or diamines such as N,N,N',N'-tetramethylethylenediamine, or diones such as tetramethylheptanedione.

[0154] The processes described herein can be carried out at temperatures ranging from -105°C to 250°C, preferably from -78°C to 185°C.

[0155] The reaction time varies as a function of the scale of the reaction and the reaction temperature, but is generally between a few minutes and 48 hours.

[0156] The processes described herein are generally carried out under standard pressure. However, it is also possible to work under pressurized or reduced pressure.

[0157] In the processes described herein, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the starting materials in a relatively large excess.

[0158] Process for preparing the compound of formula (I) Process A Formula (Ia) (where m, n, p, A, Y, R 2 , R 3 , R 4 , R 5 , R 6 , and R 7It is defined as described above, and T is oxygen (O), R 1 Compounds (which are hydrogen, hydroxyl, cyano, or C1-C6-alkyl) Equation (1) (wherein m, A, Q, Y, and R 7 It is defined as above, U 1 This refers to compounds that are hydroxyl, halogen, or C1-C6 alkoxy, Equation (2)(m, n, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 It can be prepared by a process that includes reacting an amine or salt of (as defined above) with the product as shown in Scheme 1.

[0159] Scheme 1: Process A - Synthesis of the compound of formula (Ia) [ka]

[0160] U 1Compounds of formula (1) in which is a hydroxyl group can be reacted with amines of formula (2) in the presence of a condensation reagent by methods described in the literature (e.g., Tetrahedron 2005, 61, 10827-10852). Examples of suitable condensation reagents include halogenating agents (e.g., phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride, or thionyl chloride), dehydrating agents (e.g., ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate, or methanesulfonyl chloride), and carbodiimides (e.g., N,N'-dicyclohexylcarbodiimide (DCC) or other conventional condensation (or peptide bonding) reagents (e.g., phosphorus pentoxide, polyphosphate, bis(2-oxo-3-oxazolidinyl)phosphinate chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), N,N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane, 4-(4,6-dimethoxy[1.3.5]-triazine-2-yl)-4-methylmorpholinium chloride hydrate, bromotripyrrolidinophosphonium hexafluorophosphate, or propanephosphonic anhydride (T3P)).

[0161] U 1 Compounds of formula (1) in which is a halogen can be reacted with amines of formula (2) in the presence of an acid scavenger by known methods. Suitable acid scavengers include any inorganic and organic bases conventional to such reactions, as described herein. Alkali metal carbonates, alkaline earth metal acetates, tertiary amines, or aromatic bases are preferred.

[0162] U 1 The compound of formula (1), in which is a C1-C6 alkoxy group, can optionally be reacted with an excess of the amine of formula (2) in the presence of a Lewis acid such as trimethylaluminum.

[0163] The compound of formula (1) can be prepared by one or more of the processes described herein (see processes E-L).

[0164] The amine of formula (2) is commercially available or can be prepared by following processes described in the literature (e.g., International Publication Nos. 2007 / 141009, 2013 / 064460, 2015 / 078800, 2016 / 066574, U.S. Patent Application Publication No. 2006 / 0116370, 2007 / 134799, 2014 / 177487, 2011 / 144338, European Patent No. 0807629).

[0165] Process B Formula (Ia-1) (where m, n, p, A, Y, R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 It is defined as described above, and T is oxygen (O), R 1 Compounds of hydrogen, C1-C6-alkyl, or C1-C6-alkoxy are Formula (3) (where m, n, p, A, Y, R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 It is defined as described above, and X 1 Compounds of halogens, The compound of formula (4) (wherein Q is defined as above) can be prepared by reacting it with a base (e.g., an organic base or an inorganic base) in the presence of a base, as shown in Scheme 2.

[0166] Scheme 2: Process B - Synthesis of the compound of formula (Ia-1) [ka]

[0167] Process B can be carried out as described herein in the presence of a transition metal catalyst such as a copper salt or complex, and preferably in the presence of a ligand.

[0168] The compound of formula (3) can be prepared by process N.

[0169] The compound of formula (4) may be commercially available or may be obtained by converting or derivatizing another compound of formula (4) according to well known methods.

[0170] Process C Formula (Ia-2) (in the formula, m, n, p, A, Q, R 2 , R 3 , R 4 , R 5 , R 6 , and R 7K It is defined as described above, and T is oxygen (O), R 1 Compounds of hydrogen or C1-C6-alkyl are Formula (5) (where m, n, A, Q, R 2 , R 3 , R 4 , R 5 , and R 6 This is defined as described above, and X 2 Compounds of halogens, Equation (6) (wherein p and R 7K It is defined as described above, and Y 1 CH, CR 7K , O, S, or S(=O)2, x 1 is either 1 or 2, x 2 The reagent is 0, 1, or 2. As shown in Scheme 3, it can be prepared by a process that includes reacting a metal photoredox catalyst described herein in the presence of a base (e.g., an organic base or an inorganic base).

[0171] Scheme 3: Process C - Synthesis of the compound of formula (Ia-2) [ka]

[0172] The compound of formula (5) can be prepared by process M as described herein.

[0173] Process D Formula (Ib) (where m, n, p, A, Y, R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 It is defined as described above, and T is sulfur (S), R 1 The compound (is hydrogen) Formula (Ia-2) (where m, n, p, A, Q, Y, R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 It is defined as described above, and T is oxygen (O), R 1 The compound is hydrogen. As shown in Scheme 4, it can be prepared by a process that includes a step of reacting with a thioting agent.

[0174] Scheme 4: Process D - Synthesis of the compound of formula (Ib) [ka]

[0175] Suitable thioting agents for carrying out process D include, but are not limited to, sulfur (S), sulfuric acid (H2S), sodium sulfide (Na2S), sodium hydrosulfide (NaHS), boron trisulfide (B2S3), bis(diethylaluminum) sulfide ((AlEt2)2S), ammonium sulfide ((NH4)2S), phosphorus pentasulfide (P2S5), Lawson's reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide), or polymer-supported thioting agents as described in Journal of the Chemical Society, Perkin 1 (2001), 358.

[0176] Process H is carried out in the presence of a catalytic, stoichiometric, or excess amount of base (inorganic and organic base), if desired. Preferably, these are alkali metal carbonates (e.g., sodium carbonate, potassium carbonate, sodium bicarbonate), heterocyclic aromatic bases (e.g., pyridine, picoline, lutidine, colidine), and tertiary amines (e.g., trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylpyridine-4-amine, or N-methylpiperidine).

[0177] The compounds of formula (Ia-2) are a subgroup of the compounds of formula (Ia-1) and can be prepared by one or more of the processes described herein.

[0178] Process for preparing the compound of formula (1) The compounds of formula (1) may be obtained directly by carrying out the following process, or by the transformation or derivatization of another compound of formula (1) prepared according to the process described herein. The compounds of formulas (1-a) to (1-f) are various subsets of formula (1). The compounds of formulas (1-a1) and (1-a2) are various subsets of formula (1-a), and the compounds of formulas (1-b1) and (1-b2) are various subsets of formula (1-b).

[0179] Process E Equation (1-a1) (wherein p, A, and Q are defined as above, and U 1 is a hydroxyl or C1-C6-alkoxy compound, Y 1 , Y 2 , Y 3 , and Y 4 CH and CR are independent. 7 , or N, R 7 The compounds (defined as above) Formula (10) (where A, Q, Y 1 , Y 2 , Y 3 , and Y 4 It is defined as described above, and X 3 Compounds of (which are halogens) Carbon monoxide, carbon dioxide, or formula (11) (wherein, E 1 These are halogens, cyanos, C1-C6-alkoxys, or C1-C6-alkoxycarbonyloxys. U 2 The reagent is a C1-C6 alkoxy, It can be prepared by a process that includes a reaction step as shown in Scheme 5.

[0180] Scheme 5: Process E - Synthesis of the compound of formula (1-a1) [ka]

[0181] Formula (8) (where A, Y 1 , Y 2 , Y 3 , and Y 4 X is defined as above, and X 3 Compounds of (which are halogens) are commercially available or can be prepared according to methods described in the literature (International Publication Nos. 2012 / 162254 and International Publication Nos. 2010 / 116084).

[0182] Compounds of formula (4) (wherein Q is defined as above) may be commercially available or obtained by transforming or derivatizing another compound of formula (4) according to well known methods.

[0183] The compound of formula (10) can be prepared from the compound of formula (8) by a process comprising the following: -A step of reacting the compound of formula (8) with the reagent of formula (4) in the presence of a suitable transition metal catalyst salt or complex described herein to form the compound of formula (9); - Compound of formula (9) (wherein A, Q, Y 1 , Y 2 , Y 3 , and Y 4 A step of converting (as defined above) into the compound of formula (10) in the presence of a halogenating agent such as POCl3, POBr3, PCl3, or PBr3 (International Publication No. 2012 / 162254).

[0184] The compound of formula (1-a1) can be prepared by treating the compound of formula (10) using the following: - A base (e.g., n-butyllithium (nBuLi)) and carbon dioxide or a reagent of formula (11), or - Carbon monoxide and alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0185] Process F Equation (1-a2) (wherein Q and R 7 It is defined as described above, and A is N, U 1 is a hydroxyl or C1-C6-alkoxy compound, Y 5 , Y 6 , and Y 7 CH and CR are independent. 7 , O, S, or NR 7 And, R 7 The compounds (defined as above) Formula (14) (where A, Q, Y 5 , Y 6 , and Y 7 It is defined as described above, and X 6 Compounds of (which are halogens) Carbon monoxide, carbon dioxide, or formula (11) (wherein, E 2 These are halogens, cyanos, C1-C6-alkoxys, or C1-C6-alkoxycarbonyloxys. U 2 The reagent is a C1-C6 alkoxy, It can be prepared by a process that includes a reaction step as shown in Scheme 6.

[0186] Scheme 6: Process F - Synthesis of the compound of formula (1-a2) [ka]

[0187] Formula (12) (where A, Y 5 , Y 6 , and Y 7 X is defined as above, and X 5 Compounds of (a halogen) are commercially available or can be prepared according to methods described in the literature (International Publication No. 2017 / 133667, J. Org. Chem. 2004, 79, 10311-10322, Monatshefte fuer Chemie 1986, 117, 221-230).

[0188] The compound of formula (14) can be prepared from the compound of formula (12) by a process comprising the following: -In the presence of a suitable transition metal catalyst salt or complex described herein, the compound of formula (12) is reacted with the reagent of formula (4) (wherein Q is defined above) to form formula (13) (wherein A, Q, Y 5 , Y 6 , and Y 7The process of forming a compound (as defined above); - A step of treating the compound of formula (13) with a halogenating reagent such as bromine, iodine, NCS, or NBS in the presence of a base as described herein to form the compound of formula (14).

[0189] The compound of formula (1-a2) can be prepared by treating the compound of formula (14) using the following: - A base (e.g., n-butyllithium (nBuLi)) and carbon dioxide or a reagent of formula (11), or - Carbon monoxide and alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0190] Next, the resulting compound of formula (1-a) can be further transformed in one or more steps.

[0191] A non-restrictive example of such a transformation is given below.

[0192] Process G Equation (1-b1) (wherein Q is defined as above, and A is CR 8 And, R 8 It is defined as described above, Y 1 , Y 2 , Y 3 , and Y 4 CH and CR are independent. 7 , or N, R 7 It is defined as described above, U 1 Compounds (which are hydroxyl or C1-C6-alkoxy) Formula (17) (where A, Q, Y 1 , Y 2 , Y 3 , and Y 4 It is defined as described above, and X 8 Compounds of (which are halogens) As shown in Scheme 7, it can be prepared by a process that includes a step of reacting with carbon monoxide.

[0193] Scheme 7: Process G - Synthesis of the compound of formula (1-b1) [ka]

[0194] Formula (15) (where A, Y 1 , Y 2 , Y 3 , and Y 4 X is defined as above, 7 Compounds of (where is a halogen and W is hydrogen or benzyl) are commercially available or can be prepared according to methods described in the literature (International Publication No. 2017 / 023905, International Publication No. 2017 / 112678, Monatshefte fuer Chemie 2018, 149, 1857-1864).

[0195] Compounds of formula (4) (wherein Q is defined as above) may be commercially available or obtained by transforming or derivatizing another compound of formula (4) according to well known methods.

[0196] The compound of formula (17) can be prepared from the compound of formula (15) by a process comprising the following: -In the presence of a suitable transition metal catalyst salt or complex described herein, the compound of formula (15) is reacted with the reagent of formula (4) to obtain formula (16) (wherein A, Q, W, Y 1 , Y 2 , Y 3 , and Y 4 The process of forming a compound (as defined above); -When W is hydrogen, the process involves directly converting the compound of formula (16) to the compound of formula (17) in the presence of a dehydrating agent such as POCl3, POBr3, PCl3, or PBr3; -If W is benzyl, the first step is to perform a deprotection step to obtain the compound of formula (16) (W=hydrogen), and then the compound is directly converted to the compound of formula (17) in the presence of a dehydrating agent such as POCl3, POBr3, PCl3, or PBr3.

[0197] The compound of formula (1-b1) can be prepared by treating the compound of formula (17) using the following: Carbon monoxide and alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0198] Process H Equation (1-b2) (wherein Q is defined as above, and A is CR 8 And, R 8 It is defined as described above, Y 5 , Y 6 , and Y 7 CH and CR are independent. 7E , CR 7F , CR 7G , O, S, N, or NR 7H And, R 7E , R 7F , and R 7G It is defined as described above, R 7H These are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, and -C(=O)R 21 , or -C(=O)(OR 22 ) and R 21 These are C1-C6-alkyl or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. R22 These are hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. At least Y 5 , Y 6 , and Y 7 CH, CR 7E , CR 7F , or CR 7G And, U 1 Compounds (which are hydroxyl or C1-C6-alkoxy) Formula (20) (where A, Q, Y 5 , Y 6 , and Y 7 It is defined as described above, and X 11 Compounds of (which are halogens) As shown in Scheme 8, it can be prepared by a process that includes a step of reacting with carbon monoxide.

[0199] Scheme 8: Process H - Synthesis of the compound of formula (1-b2) [ka]

[0200] Formula (18) (where A, Y 5 , Y 6 , and Y 7 X is defined as above, 10Compounds of (where is a halogen and W is hydrogen or benzyl) are commercially available or can be prepared according to methods described in the literature (International Publication Nos. 2005 / 095401, 2018 / 067422, 2016 / 106106, 2014 / 144455, and WO2013 / 086397).

[0201] The compound of formula (20) can be prepared from the compound of formula (18) by a process comprising the following steps: -A step of reacting the compound of formula (18) with the reagent of formula (4) in the presence of a suitable transition metal catalyst salt or complex described herein to form the compound of formula (19); -When W is hydrogen, the compound of formula (19) (wherein A, Q, W, Y 5 , Y 6 , and Y 7 The process of directly converting (as defined above) into the compound of formula (20) in the presence of a dehydrating agent such as POCl3, POBr3, PCl3, or PBr3. -If W is benzyl, the first step is to perform a deprotection step to obtain the compound of formula (19) (W=hydrogen), and then the compound is directly converted to the compound of formula (20) in the presence of a dehydrating agent such as POCl3, POBr3, PCl3, or PBr3.

[0202] The compound of formula (1-b2) can be prepared by treating the compound of formula (20) using the following: Carbon monoxide and alcohol in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0203] Process I Equation (1-c) (wherein Q and R 7K It is defined as described above, and A is N, U 1 is a hydroxyl or C1-C6-alkoxy compound, Y 8 is O, S, or NR 7KA And, R7KA These are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, and -C(=O)R 21 , or -C(=O)(OR 22 ) and R 21 and R 22 It is defined as described above, x 3 The compound is (1, 2, or 3), Formula (24) (where p, A, Q, Y 8 , and R 7K A compound of the above definition) is carbon dioxide or formula (11) (wherein, E 3 These are halogens, cyanos, C1-C6-alkoxys, or C1-C6-alkoxycarbonyloxys. U 2 The reagent is a C1-C6 alkoxy, It can be prepared by a process that includes a reaction step as shown in Scheme 9.

[0204] Scheme 9: Process I - Synthesis of the compound of formula (1-c) [ka]

[0205] Equations (21) and (22) (wherein p, x) 3 , A, Y 8 , and R 7K X is defined as above, 12 , X 13 , and X 14 Compounds (where the halogen is) are commercially available.

[0206] Compounds of formula (4) (wherein Q is defined as above) may be commercially available or obtained by transforming or derivatizing another compound of formula (4) according to well known methods.

[0207] The compound of formula (24) can be prepared from the compound of formula (21) by a process comprising the following: - A step of reacting the compound of formula (21) with the reagent of formula (22) in the presence of a base and, optionally, a suitable transition metal catalyst salt or complex as described herein, to form the compound of formula (23); -A step of reacting the compound of formula (23) with the reagent of formula (4) in the presence of a base and a suitable transition metal catalyst salt or complex as described herein to form the compound of formula (24).

[0208] The compounds of formula (1-c) can be prepared by treating the compound of formula (24) with a base (e.g., nBuLi or lithium diisopropylamine) and carbon dioxide or the reagent of formula (11).

[0209] Process J Equation (1-d) (wherein p, Q, and R 7K It is defined as described above, and A is CR 8 And, R 8 It is defined as described above, U 1 is a hydroxyl or C1-C6-alkoxy compound, Y 8 is O, S, or NR 7KA And, R 7KA These are hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, and -C(=O)R 21 , or -C(=O)(OR 22 ) and R 21 and R 22 It is defined as described above, x 3 A compound of which is 1 or 2, Formula (27) (where p, A, Q, Y 8 , R 7K , and x 3 A compound of the above definition) is carbon dioxide or formula (11) (wherein, U 2 It is a C1-C6 alkoxy, E 3The reagent is a halogen, cyano, C1-C6-alkoxy, or C1-C6-alkoxycarbonyloxy, It can be prepared by reacting as shown in Scheme 10.

[0210] Scheme 10: Process J - Synthesis of the compound of formula (1-d) [ka]

[0211] Compounds of formulas (22) and (25) are commercially available.

[0212] The compound of formula (4) may be commercially available or may be obtained by converting or derivatizing another compound of formula (4) according to well known methods.

[0213] The compound of formula (27) can be prepared from the compound of formula (25) (wherein A is defined as above and Z1 is hydroxyl or halogen) by a process comprising the following steps: -In the presence of a base and optionally in the presence of a suitable transition metal catalyst salt or complex described herein, the compound of formula (25) is converted to formula (22) (wherein p, x 3 , and Y 8 After reacting with the reagent (defined above), a halogenation step (for example, using bromine) is performed to obtain formula (26) (wherein p, x 3 , A, and Y 8 X is defined as above, 15 The process of forming a compound of (which is a halogen); -A step of reacting the compound of formula (26) with the reagent of formula (4) in the presence of a suitable transition metal catalyst salt or complex described herein to form the compound of formula (27).

[0214] The compounds of formula (1-d) can be prepared by treating the compound of formula (27) with a base (e.g., nBuLi or lithium diisopropylamine) and carbon dioxide or the reagent of formula (11).

[0215] Process K Equation (1-e) (wherein p, Q, and R 7K It is defined as described above, and A is N, Y 1 CH, CR 7K , O, S, or S(=O)2, R 7K It is defined as described above, U 1 It is a C1-C6 alkoxy, x 1 is 1 or 2, x 2 Compounds (where is 0, 1, or 2) Equation (28) (wherein A, Q, and U1 are defined as above) X 16 Compounds of halogens, Formula (6) (where p, x 1 , Y 1 , and R 7K The reagents (as defined above) can be prepared by a process that includes reacting them in the presence of a metal photoredox catalyst and a base (e.g., an organic base or an inorganic base) as shown in Scheme 11.

[0216] Scheme 11: Process K - Synthesis of the compound of formula (1-e) [ka]

[0217] Process K can be carried out under the same conditions as process C.

[0218] The compound of formula (28) can be prepared by process M as described herein.

[0219] Process L Equation (1-f) (wherein p, Q, and R 7 It is defined as described above, and A is N, Y is a saturated or partially saturated 5- to 8-membered carbocyclyl condensed to a pyridine ring / pyridazine ring, or a saturated or partially saturated 5- to 8-membered heterocyclyl. U 1 The compounds (which are C1-C6 alkoxys) are Formula (33) (where p, A, Q, Y, U 1 , and R 7 It is defined as described above, X 17 Compounds of halogens, This can be prepared by a process that includes reacting the reagent of formula (4) (wherein Q is defined as above) with a base (e.g., an organic base or an inorganic base), and optionally in the presence of a suitable transition metal catalyst salt or complex.

[0220] Scheme 12: Process L - Synthesis of the compound of formula (1-f) [ka]

[0221] The compound of formula (33) is of formula (32) (wherein p, A, Y, U 1 , and R 7 It can be prepared from the compound (as defined above) in the presence of a halogenating agent such as POCl3, POBr3, PCl3, or PBr3.

[0222] The compound of formula (32) can be prepared from the compounds of formulas (29) and (30) by the method described in the literature (International Publication No. 2018 / 125800).

[0223] Compounds of formula (29) and formula (30) are commercially available.

[0224] Equations (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) (wherein U 1Compounds of the form (wherein U is a C1-C6 alkoxy) are converted by known functional group interconversion methods, for example, by hydrolysis of the ester group with lithium hydroxide (LiOH)-containing tetrahydrofuran / water to obtain formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) (wherein U is a C1-C6 alkoxy). 1 It can be converted into compounds of a hydroxyl group.

[0225] Formulas (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) (wherein U 1 Compounds of formula (1-a), (1-b), (1-c), (1-d), (1-e), and (1-f) (wherein U is hydroxyl) are obtained by known methods in the presence of a halogenating agent. 1 It can be converted to compounds of (which are halogens). Suitable halogenating reagents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride, or thionyl chloride.

[0226] Process for preparing the compound of formula (5) Process M Formula (5) (where A, Q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and X 2 The compound of process D is defined as formula (28) (wherein A, Q, and X 2 It is defined as described above.

[0227] U 1 It is a C1-C6 alkoxy, X 18 Compounds of (which are halogens) Equation (2)(m, n, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6It can be prepared by a process that includes reacting an amine or salt of (as defined above) with the amine as shown in Scheme 13.

[0228] Scheme 13: Process M - Synthesis of the compound of formula (5) [ka]

[0229] Process M can be carried out using the same reaction conditions as described in Process A.

[0230] The compound of formula (28) can be prepared by reacting the compound of formula (34) with the reagent of formula (4) (wherein Q is defined above) in the presence of a base and optionally in the presence of a suitable transition metal catalyst salt or complex as described herein.

[0231] The compound of formula (34) is commercially available.

[0232] The compound of formula (4) may be commercially available or may be obtained by converting or derivatizing another compound of formula (4) according to well known methods.

[0233] Formula (28) (where U 1 Compounds of the form (wherein U is a C1-C6 alkoxy) are converted by known functional group interconversion methods, for example, by hydrolysis of the ester group with lithium hydroxide (LiOH)-containing tetrahydrofuran / water, to form formula (28) (wherein U 1 It can be converted into compounds of a hydroxyl group.

[0234] The compound of formula (28) (wherein U1 is hydroxyl) is prepared by a well-known method in the presence of a halogenating agent. 1 It can be converted to compounds of (which are halogens). Suitable halogenating reagents include, but are not limited to, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus trichloride oxide, oxalyl chloride, or thionyl chloride.

[0235] Process for preparing the compound of formula (3) Process facility Formula (3) (where m, n, p, A, Y, R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 It is defined as described above, and X 1 Compounds of halogens are Formula (36) (where p, A, Y, X 1 , and R 7 It is defined as described above, U 1 Compounds that are hydroxyl or C1-C6-alkoxy are Equation (2)(m, n, R 2 , R 3 , R 4 , R 5 , and R 6 It can be prepared by a process that includes reacting an amine or salt of (as defined above) with the product as shown in Scheme 14.

[0236] Scheme 14: Process N - Synthesis of the compound of formula (3) [ka]

[0237] Process N can be carried out using the same reaction conditions as described in Process A.

[0238] The compound of formula (36) is of formula (35) (p, A, Y, X 1 , and R 7 It is defined as above, and G can be prepared by treating a compound of hydrogen, halogen, methylsulfonyloxy, trifluoromethylsulfonyloxy, or p-tolylsulfonyloxy as follows: - A base (for example, nBuLi if G is a halogen, or lithium diisopropylamine if G=H) and carbon dioxide or a reagent of formula (11), - Carbon monoxide and alcohols in the presence of a suitable transition metal catalyst salt or complex as described herein (where G is a halogen, methylsulfonyloxy, trifluoromethylsulfonyloxy, or p-tolylsulfonyloxy).

[0239] Is the amine of formula (35) commercially available, or is it mentioned in the literature (International Publication Nos. 2017 / 004500, 2017 / 112719, 2016 / 115272, 2011 / 015343, 2017 / 023905, 2017 / 112678, Monatshefte fuer Chemie 2018, 149)? It can be prepared according to the methods described in International Publications 1857-1864, International Publication Nos. 2005 / 095401, 2018 / 067422, 2016 / 106106, 2014 / 144455, 2013 / 086397, 2014 / 0121198, 2011 / 145287, 2012 / 098387, and Eur. J. Med. Chem. 2017, 138, 816-829).

[0240] The compounds according to the present invention can be prepared according to the processes described above. However, those skilled in the art will understand, based on common technical knowledge and available publications, that these processes can be adapted according to the specifications of each compound according to the present invention whose synthesis is desired.

[0241] Intermediate for preparing the compound of formula (I) The present invention also relates to intermediates for preparing the compound of formula (I).

[0242] Therefore, the present invention is based on formula (1):

[0243] [ka]

[0244] (wherein A is nitrogen (N) or CR 8 and R 8 is hydrogen, halogen, cyano, or C1-C4-alkyl, U 1 is hydroxyl, halogen, or C1-C6-alkoxy, Ring Y together with a pyridine ring or a pyridazine ring respectively forms a bicyclic heterocyclyl or a bicyclic heteroaryl, but the resulting bicyclic heteroaryl is not quinoline, p is 0, 1, 2, 3, or 4, R 7 is halogen, cyano, nitro, hydroxyl, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2, or -S(=O)2N(R 24 )2, and 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, and C1-C6-haloalkylsulfonyl are optionally substituted with 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, and C3-C8-halocycloalkyl. C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. and R 20 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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, and C3-C8-halocycloalkyl groups. and C3-C8-cycloalkyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl, R 21 、R 22 、R 23 、and R 24 are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, and C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl, or two substituents R 7 together with the carbon atom to which they are attached form a C3-C8-cycloalkyl ring, Q is C6-C 14 -aryl, C3-C 12 -carbocyclyl, a 3- to 14-membered heterocyclyl, or a 5- to 14-membered heteroaryl, and C6-C 14 -aryl, C3-C 12-Carbocyclyls, 3- to 14-membered heterocyclyls, and 5- to 14-membered heteroaryls include halogens, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-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-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 , -NR 26 C(=O)R 27 -C(=O)N(R 28 )2, C(=S)R 29 -C(=S)N(R 30 )2, -C(=NR 31 )R 32 -C(=NOR 33 )R 34 , and -N(R 35 )1 to 5 Q independently selected from the group consisting of 2 S Substituting as desired with substituents, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkyls Ruffinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are optionally substituted with 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-membered to 7-membered heterocyclyl. The aforementioned C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, and 5- to 14-membered heteroaryl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyls may be optionally substituted with two substituents that, in order, combine with the carbon atoms to which they are bonded to form a C3-C8-cycloalkyl. R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , and R 34 These are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, or C1-C6-alkoxy, The C1-C6-alkyl, C1-C6-haloalkyl, and C1-C6-alkoxy elements are optionally substituted with 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-membered to 7-membered heterocyclyl. and R 35 These are independently hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, or C3-C8-cycloalkyl, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, and C2-C6-haloalkenyl are optionally substituted with 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-membered to 7-membered heterocyclyl. The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl groups. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl compounds (which may be optionally substituted with two substituents that, in order, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl group), The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0245] Therefore, similarly, the present invention also relates to formula (1):

[0246] [ka]

[0247] (In the formula, A is nitrogen (N) or CR 8 And, R 8 These are hydrogen, halogen, or C1-C4-alkyl, U 1 These are hydroxyl, halogen, or C1-C6 alkoxy compounds. Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. The resulting bicyclic heteroaryl is not quinoline, p is 0, 1, 2, 3, or 4. R 7This includes halogens, cyano, nitro, hydroxyl, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2, or -S(=O)2N(R 24 )2, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, and C1-C6-haloalkylsulfonyl are optionally substituted with 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, and C3-C8-halocycloalkyl. C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. and R 20 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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, and C3-C8-halocycloalkyl groups. and The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 21 , R 22 , R 23 , and R 24 These are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. or Two substituents R 7 These, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring. 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 -Carbocyclyls, 3- to 14-membered heterocyclyls, and 5- to 14-membered heteroaryls include halogens, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-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-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 , -NR 26 C(=O)R 27-C(=O)N(R 28 )2, C(=S)R 29 -C(=S)N(R 30 )2, -C(=NR 31 )R 32 -C(=NOR 33 )R 34 , and -N(R 35 )1 to 5 Q independently selected from the group consisting of 2 S Substituting as desired with substituents, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkyls Ruffinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are optionally substituted with 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-membered to 7-membered heterocyclyl. The C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, and 5- to 14-membered heteroaryl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of 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-C6-alkenyl, and 3- to 7-membered heterocyclyl, The C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl are optionally substituted with 2 substituents which together with the carbon atoms to which they are attached form a C3-C8-cycloalkyl, R 25 、R 26 、R 27 、R 28 、R 29 、R 30 、R 31 、R 32 、R 33 、and R 34 are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, or C1-C6-alkoxy, The C1-C6-alkyl, C1-C6-haloalkyl, and C1-C6-alkoxy are optionally substituted with 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 R 35is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, or C3-C8-cycloalkyl, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, and C2-C6-haloalkenyl are optionally substituted with 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-membered to 7-membered heterocyclyl. The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl groups. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl compounds (which may be optionally substituted with two substituents that, in order, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl group), The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0248] Therefore, the present invention also relates to formula (1):

[0249] [ka]

[0250] (In the formula, A is CR 8 And, R 8 These are hydrogen, halogen, cyano, or C1-C4-alkyl, U 1 These are hydroxyl, halogen, or C1-C6 alkoxy compounds. Ring Y forms a quinoline ring together with the pyridine ring. p is 0, 1, 2, 3, or 4. R 7 This includes halogens, cyano, nitro, hydroxyl, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2, or -S(=O)2N(R 24 )2, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, and C1-C6-haloalkylsulfonyl are optionally substituted with 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, and C3-C8-halocycloalkyl. C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. and R 20 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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, and C3-C8-halocycloalkyl groups. and The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 21 , R 22 , R 23 , and R 24 These are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. Q is phenyl, Phenyl is a halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C 6-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-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 , -NR 26 C(=O)R 27 -C(=O)N(R 28 )2, C(=S)R 29 -C(=S)N(R 30 )2, -C(=NR 31 )R 32 -C(=NOR 33 )R 34 , and -N(R 35 )1 to 5 Q independently selected from the group consisting of 2 S Substituting as desired with substituents, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkyls Ruffinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are optionally substituted with 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-membered to 7-membered heterocyclyl. The aforementioned C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, and 5- to 14-membered heteroaryl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyls may be optionally substituted with two substituents that, in order, combine with the carbon atoms to which they are bonded to form a C3-C8-cycloalkyl. R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , and R 34 These are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, or C1-C6-alkoxy, The C1-C6-alkyl, C1-C6-haloalkyl, and C1-C6-alkoxy elements are optionally substituted with 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-membered to 7-membered heterocyclyl. and R 35 These are independently hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, or C3-C8-cycloalkyl, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, and C2-C6-haloalkenyl are optionally substituted with 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-membered to 7-membered heterocyclyl. The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl groups. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl compounds (which may be optionally substituted with two substituents that, in order, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl group), The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0251] Therefore, similarly, the present invention also relates to formula (1):

[0252] [ka]

[0253] (In the formula, A is CR 8 And, R 8 These are hydrogen, halogen, or C1-C4-alkyl, U 1 These are hydroxyl, halogen, or C1-C6 alkoxy compounds. Ring Y forms a quinoline ring together with the pyridine ring. p is 0, 1, 2, 3, or 4. R 7This includes halogens, cyano, nitro, hydroxyl, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2, or -S(=O)2N(R 24 )2, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, and C1-C6-haloalkylsulfonyl are optionally substituted with 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, and C3-C8-halocycloalkyl. C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. and R 20 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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, and C3-C8-halocycloalkyl groups. and The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 21 , R 22 , R 23 , and R 24 These are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. Q is phenyl, Phenyl is a halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C 6-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-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C1-C6-alkyl)3, -Si(C1-C6-alkyl)3, -OC(=O)R 25 , -NR 26 C(=O)R 27 -C(=O)N(R 28 )2, C(=S)R 29 -C(=S)N(R 30 )2, -C(=NR 31 )R 32 -C(=NOR 33 )R 34 , and -N(R 35 )1 to 5 Q independently selected from the group consisting of 2 S Substituting as desired with substituents, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkylcarbonyl, C1-C6-haloalkylcarbonyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkyls Ruffinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are optionally substituted with 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-membered to 7-membered heterocyclyl. The aforementioned C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C6-cycloalkenyl, 3- to 7-membered heterocyclyl, and 5- to 14-membered heteroaryl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyls may be optionally substituted with two substituents that, in order, combine with the carbon atoms to which they are bonded to form a C3-C8-cycloalkyl. R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , and R 34 These are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, or C1-C6-alkoxy, The C1-C6-alkyl, C1-C6-haloalkyl, and C1-C6-alkoxy elements are optionally substituted with 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-membered to 7-membered heterocyclyl. and R 35 is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, or C3-C8-cycloalkyl, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, and C2-C6-haloalkenyl are optionally substituted with 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-membered to 7-membered heterocyclyl. The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, and 3- to 7-membered heterocyclyl groups. The aforementioned C3-C8-cycloalkyl, C3-C8-halocycloalkyl, and 3- to 7-membered heterocyclyl compounds (which may be optionally substituted with two substituents that, in order, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl group), The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0254] The present invention also includes formula (3):

[0255] [ka]

[0256] (In the formula, X 1 is halogen, T is oxygen (O), n is 1, m is 1, A is nitrogen (N) or CR 8 And, (In the formula, R 8 These are hydrogen, halogen, cyano, or C1-C4-alkyl, R 1 These are hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, and -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 -S(=O)2R 12 -C(=O)N(R13 )2, or -S(=O)2N(R 14 )2, R 10 , R 11 , and R 12 These are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl, R 13 and R 14 These are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl. R 2 and R 3 It is independently hydrogen, R 4 and R 5 These are independently hydrogen or fluoro, R 6 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, C1-C3-alkoxy, or C1-C3-haloalkoxy, C1-C3-alkoxy and C1-C3-haloalkoxy are C3-C 12 -Carbocyclyl, C6-C 14 - Independently substituted with one substituent selected from the group consisting of aryls, 3- to 14-membered heterocyclines, and 5- to 14-membered heteroaryls, Said C3-C 12 -Carbocyclyl, C6-C 14 -aryls, 3- to 14-membered heterocyclines, and 5- to 14-membered heteroaryls are sequentially divided into 1 to 4 R 6S Substituting as desired with substituents, C3-C 12 -Carbocyclyl, C6-C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C3-C12 -Carbocyclyloxy, C6-C 14 - Aryloxy, 5- to 14-membered heteroaryloxy, and 3- to 14-membered heterocyclyloxy have 1 to 4 R 6S Substituting as desired with substituents, R 6S These are independently halogen, cyano, isocyano, nitro, hydroxyl, oxo, 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, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1- C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5-membered or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -N(R) 15 )2, -C(=O)R 16 , -C(=O)(OR 17 ), -C(=O)N(R 18 )2, -S(=O)2N(R 19 )2, -O-Si(C1-C6-alkyl)3, or -Si(C1-C6-alkyl)3, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkyls The ruhonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are further optionally substituted with 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-membered to 7-membered heterocyclyl. and The aforementioned C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5-membered or 6-membered heteroaryl, and 3- to 7-membered heterocyclyl are further optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl, or Two C1-C6-alkyl substituents bonded to the same carbon atom form a C3-C8-cycloalkyl ring. or 2 R 6SThe substituents, if desired, combine with the carbon atoms to which they are bonded to form a C3-C8-cycloalkyl ring. and R 15 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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-membered to 7-membered heterocyclyl groups. and The C3-C8-cycloalkyl group is further optionally substituted with 1 to 4 substituents independently selected from the group consisting of 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 16 , R 17 , R 18 , and R 19 These are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl, The C1-C6-alkyl or C1-C6-haloalkyl group may be further optionally substituted with 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-membered to 7-membered heterocyclyl groups. Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. p is 0, 1, 2, 3, or 4. R 7 This includes halogens, cyano, nitro, hydroxyl, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2, or -S(=O)2N(R 24 )2, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, and C1-C6-haloalkylsulfonyl are optionally substituted with 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, and C3-C8-halocycloalkyl. C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. and R 20 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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, and C3-C8-halocycloalkyl groups. and The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 21 , R 22 , R 23 , and R 24 These are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. or Two substituents R 7 These are compounds (which, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring), The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0257] Similarly, the present invention relates to formula (3):

[0258] [ka]

[0259] (In the formula, X 1 is halogen, T is oxygen (O), n is 1, m is 1, A is nitrogen (N) or CR 8 And, R 8 is hydrogen or halogen, R 1 These are hydrogen, hydroxyl, cyano, C1-C6-alkyl, C1-C6-alkoxy, and -C(=O)R 10 , -C(=O)(OR 11 ), -S(=O)R 12 -S(=O)2R 12 -C(=O)N(R 13 )2, or -S(=O)2N(R 14 )2, R 10 , R 11 , and R 12These are independently C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl, R 13 and R 14 These are independently hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C8-cycloalkyl, or C2-C6-alkenyl. R 2 and R 3 It is independently hydrogen, R 4 and R 5 These are independently hydrogen or fluoro, R 6 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, C1-C3-alkoxy, or C1-C3-haloalkoxy, C1-C3-alkoxy and C1-C3-haloalkoxy are C3-C 12 -Carbocyclyl, C6-C 14 - Independently substituted with one substituent selected from the group consisting of aryls, 3- to 14-membered heterocyclines, and 5- to 14-membered heteroaryls, Said C3-C 12 -Carbocyclyl, C6-C 14 -aryls, 3- to 14-membered heterocyclines, and 5- to 14-membered heteroaryls are sequentially divided into 1 to 4 R 6S Substituting as desired with substituents, 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, and 3- to 14-membered heterocyclyloxy have 1 to 4 R 6SSubstituting as desired with substituents, R 6S This includes halogens, cyano, isocyano, nitro, hydroxyl, oxo, 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, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C 6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C3-C8-cycloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C3-C8-cycloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5-membered or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -N(R) 15 )2, -C(=O)R 16 , -C(=O)(OR 17 ), -C(=O)N(R 18 )2, -S(=O)2N(R 19 )2, -O-Si(C1-C6-alkyl)3, or -Si(C1-C6-alkyl)3, The aforementioned C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-alkenyloxy, C2-C6-haloalkenyloxy, C1-C6-alkylsulfanyl, C1-C6-haloalkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkyls The ruhonyl, C1-C6-haloalkylsulfonyl, -O-Si(C1-C6-alkyl)3, and -Si(C1-C6-alkyl)3 are further optionally substituted with 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-membered to 7-membered heterocyclyl. and The aforementioned C3-C8-cycloalkylsulfanyl, C3-C8-cycloalkylsulfinyl, C3-C8-cycloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkenyl, C6-C 14 -aryl, 5-membered or 6-membered heteroaryl, and 3- to 7-membered heterocyclyl are further optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl, or Two C1-C6-alkyl substituents bonded to the same carbon atom form a C3-C8-cycloalkyl ring. or 2 R 6SThe substituents, if desired, combine with the carbon atoms to which they are bonded to form a C3-C8-cycloalkyl ring. and R 15 is hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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-membered to 7-membered heterocyclyl groups. and The C3-C8-cycloalkyl group is further optionally substituted with 1 to 4 substituents independently selected from the group consisting of 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 16 , R 17 , R 18 , and R 19 These are independently hydrogen, C1-C6-alkyl, or C1-C6-haloalkyl, The C1-C6-alkyl or C1-C6-haloalkyl group may be further optionally substituted with 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-membered to 7-membered heterocyclyl groups. Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. p is 0, 1, 2, 3, or 4. R7 This includes halogens, cyano, nitro, hydroxyl, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl, -N(R 20 )2, -C(=O)R 21 , -C(=O)(OR 22 ), -C(=O)N(R 23 )2, or -S(=O)2N(R 24 )2, 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, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, and C1-C6-haloalkylsulfonyl are optionally substituted with 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, and C3-C8-halocycloalkyl. C3-C8-cycloalkyl and C3-C8-cycloalkenyl are optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. and R 20 These are independently hydrogen, C1-C6-alkyl, or C3-C8-cycloalkyl, The C1-C6-alkyl group is further optionally substituted with 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, and C3-C8-halocycloalkyl groups. and The C3-C8-cycloalkyl group is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogens, 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-C6-alkenyl, C3-C8-cycloalkyl, and C3-C8-halocycloalkyl. R 21 , R 22 , R 23 , and R 24 These are independently hydrogen, C1-C6-alkyl or C1-C6-haloalkyl, C1-C6-alkyl and C1-C6-haloalkyl are further optionally substituted with 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, and C3-C8-halocycloalkyl. or Two substituents R 7 These are compounds (which, together with the carbon atoms to which they are bonded, form a C3-C8-cycloalkyl ring), The present invention relates to the N-oxides, salts, and solvates thereof, as well as the solvates of the salts and N-oxides thereof.

[0260] The present invention also relates to formula (4): Q-OH(4) (In the formula, Q is,

[0261] [ka] or [ka]

[0262] And, §2 is the bonding point to OH, Q S1 It is fluoro, Q S2 These are C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl, or C3-C6-halocycloalkyl,

[0263] [Table 1] This concerns intermediates (that do not represent).

[0264] The present invention also relates to formula (4): Q-OH(4) (In the formula, Q is the formula:

[0265] [ka] or [ka] It is the basis of,

[0266] §2 is the bonding point to OH, Q S1 It is fluoro, Q S2 These are C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C4-alkynyl, cyclopropyl, cyclobutyl, or C3-C6-halocycloalkyl,

[0267] [Table 2] This concerns intermediates (that do not represent).

[0268] Compositions and formulations The present invention further relates to compositions, particularly compositions for controlling undesirable microorganisms. The compositions can be applied to microorganisms and / or their habitats.

[0269] This composition comprises at least one compound of formula (I) and at least one agricultural auxiliary agent, such as a carrier and / or a surfactant.

[0270] Carriers are generally inert, solid or liquid, natural or synthetic, organic or inorganic substances. Carriers generally improve the application of compounds to plants, plant parts, or seeds, for example. 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 such as fine silica, alumina, and silicates; and synthetic rock powders. Typical solid carriers useful 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 husks, corn cobs, and tobacco stalks. Suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include, for example, polar and nonpolar organic chemical liquids from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffin, alkylbenzene, xylene, toluene, tetrahydronaphthalene, alkylnaphthalene, chlorinated aliphatic hydrocarbons such as chlorinated aromatic or chlorobenzene, chloroethylene, or methylene chloride), alcohols and polyols (such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, or glycol, which may be substituted, etherified, and / or esterified), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone), esters (including oils and fats) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide or fatty acid amides) and their esters, lactams (such as N-alkylpyrrolidone, especially N-methylpyrrolidone) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide), and oils of plant or animal origin. The carrier may also be a liquefied gas extender, i.e., a liquid gas under standard temperature and pressure, such as aerosol propellants such as halohydrocarbons, butane, propane, nitrogen, or carbon dioxide.

[0271] Preferred solid supports are selected from clay, talc, and silica.

[0272] Preferred liquid carriers are selected from water, fatty acid amides and their esters, aromatic and non-aromatic hydrocarbons, lactams, and carbonate esters.

[0273] The amount of the carrier is typically in the range of 1 to 99.99% by weight of the composition, preferably 5 to 99.9% by weight, more preferably 10 to 99.5% by weight, and most preferably 20 to 99% by weight.

[0274] The liquid carrier is typically present in the range of 20–90% by weight of the composition, for example, 30–80% by weight.

[0275] The solid carrier is typically present in the composition in an amount of 0 to 50% by weight, preferably 5 to 45% by weight, for example, within the range of 10 to 30% by weight.

[0276] If the composition contains two or more carriers, the outlined range refers to the total amount of carriers.

[0277] Surfactants can be ionic (cationic or anionic), amphoteric or nonionic surfactants, such as ionic or nonionic emulsifiers, foaming agents, dispersants, wetting agents, penetration enhancers, and any mixtures 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, such as alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols) and their ethoxylates (tristyrylphenols) This includes, but is 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 alkylbenzene sulfonates), phosphate esters, protein hydrolysates, lignosulfite wastewater, and methylcellulose. References to salts in this paragraph preferably refer to alkali salts, alkaline earth salts, and ammonium salts, respectively.

[0278] Preferred surfactants are selected from polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, alkylbenzene sulfonates such as calcium dodecylbenzenesulfonate, castor oil ethoxylates, sodium lignosulfonate, and arylphenol ethoxylates such as tristyrylphenol ethoxylate.

[0279] The amount of surfactant is typically in the range of 5 to 40% by weight of the composition, for example, 10 to 20% by weight.

[0280] Further examples of suitable additives include water repellents, desiccants, binders (adhesives, tackifiers, fixatives such as carboxymethylcellulose, natural and synthetic polymers in powder, granular, or latex form such as gum arabic, polyvinyl alcohol, and polyvinyl acetate, natural and synthetic phospholipids such as cephalin and lecithin, polyvinylpyrrolidone, and tyrose), thickeners and secondary thickeners (cellulose ethers, acrylic acid derivatives, xanthan gum, modified clay, e.g., products available under the name BENTONE®, and fine silica), stabilizers (e.g., low-temperature stabilizers), preservatives (e.g., dichlorophene and benzyl alcohol), This includes (formal methimal), antioxidants, light stabilizers, especially UV stabilizers, or other agents that improve chemical and / or physical stability), dyes or pigments (e.g., inorganic pigments such as iron oxide, titanium dioxide, and Prussian blue; organic dyes such as alizarin, azo, and metal phthalocyanine dyes), defoamers (e.g., silicone defoamers and magnesium stearate), antifreezes, stickers, gibberellins, processing aids, mineral oils, vegetable oils, fragrances, waxes, nutrients (including micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc), protective colloids, thixotropic substances, penetrants, metal ion chelating agents, and compound-forming agents.

[0281] The selection of excipients depends on the intended application mode of the compound of formula (I) and / or the physical properties of the compound. Furthermore, excipients may be selected to impart specific properties (technical, physical, and / or biological properties) to the composition or the form of use prepared therefrom. The selection of excipients may allow the composition to be customized to specific needs.

[0282] The compositions of the present invention may be provided to end users as ready-to-use formulations. That is, the compositions may be applied directly to plants or seeds by a suitable device such as a spray or dispensing device. Alternatively, the compositions may be provided to end users in the form of concentrates that need to be diluted with water, preferably before use.

[0283] The compositions of the present invention can be prepared by conventional methods, for example, by mixing a compound of formula (I) with one or more suitable auxiliary agents as disclosed above.

[0284] The composition contains a bactericidal effective amount of the compound of formula (I). The term "effective amount" means an amount sufficient to control harmful fungi in cultivated plants or to protect the material without causing substantial damage to the treated plant. Such an amount can vary widely and depends on various factors such as the fungal species to be controlled, the cultivated plant or material being treated, climatic conditions, and the specific compound of formula (I) used. Typically, the composition according to the present invention contains 0.01 to 99% by weight, preferably 0.05 to 98% by weight, more preferably 0.1 to 95% by weight, even more preferably 0.5 to 90% by weight, and most preferably 1 to 80% by weight of the compound of formula (I). It is possible for a composition to contain two or more compounds of the present invention. In such cases, the outlined range refers to the total amount of the compounds of the present invention.

[0285] The compositions of the present invention may be any conventional composition type, such as solutions (e.g., aqueous solutions), emulsions, aqueous and oily suspensions, powders (e.g., wettable powders, soluble powders), fine powders, pastes, granules (e.g., soluble granules, spray granules), suspoemulsion concentrates, natural or synthetic products impregnated with the compound of formula (I), fertilizers, and microencapsulated polymeric substances. The compound of formula (I) may exist in suspension, 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), emulsions (e.g., EC), emulsions (e.g., EW, EO, ES, ME, SE), capsules (e.g., CS, ZC), pastes, lozenges, wettable powders or fine powders (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). An overview is provided in "Catalogue of pesticide formulation types and international coding system" (Technical Monograph No. 2, 6th Ed. May 2008, Croplife International).

[0286] Preferably, the composition of the present invention is one of the following types: EC, SC, FS, SE, OD, and WG, more preferably EC, SC, OD, and WG.

[0287] Examples of composition types and further details regarding their preparation are given below. If two or more compounds of the present invention are present, the approximate amount of a compound of the present invention refers to the total amount of the compound of the present invention. This applies mutatis mutandis to any further components of the composition, for example, if there are two or more representatives of such components, such as wetting agents or binders.

[0288] i) Water-soluble concentrates (SL, LS) Add 10-60% by weight of at least one compound of formula (I) and 5-15% by weight of a surfactant (e.g., polyoxyethylene fatty alcohol ether) to such amounts of water and / or a water-soluble solvent (e.g., a carbonate such as propylene glycol or propylene carbonate) to make a total volume of 100% by weight. Dilute this concentrate with water before application.

[0289] ii) Dispersible Concentrate (DC) Dissolve 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) in such amounts of an organic solvent (e.g., cyclohexanone) to a total volume of 100% by weight. Dilution with water yields a dispersion.

[0290] iii) Emulsion (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 added in such amounts as a water-insoluble organic solvent (e.g., an aromatic hydrocarbon or fatty acid amide), and additional water-soluble solvents as needed, to a total volume of 100% by weight. Dilution with water yields an emulsion.

[0291] iv) Emulsions (EW, EO, ES) Dissolve 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) in 20-40% by weight of a water-insoluble organic solvent (e.g., an aromatic hydrocarbon). Add this mixture to the same amount of water using an emulsifier until the total volume is 100% by weight. The resulting composition is a homogeneous emulsion. This emulsion may be further diluted with water before application.

[0292] v) Suspensions and suspension concentrates v-1) Aqueous (SC, FS) For example, using a suitable grinding apparatus such as a stirring ball mill, 20-60% by weight of at least one compound of formula (I) is ground with the addition of 2-10% by weight of surfactants (e.g., sodium ligninsulfonate and polyoxyethylene fatty alcohol ether), and 0.1-2% by weight of a thickener (e.g., xanthan gum) and water are added to obtain a fine suspension of the active substance. The amount of water added is such that the total amount is 100% by weight. Dilution with water yields a stable suspension of the active substance. For FS type compositions, up to 40% by weight of a binder (e.g., polyvinyl alcohol) is added.

[0293] v-2) Oil-based (OD, OF) For example, using a suitable grinding apparatus such as a stirred ball mill, 20-60% by weight of at least one compound of formula (I) is ground with the addition of 2-10% by weight of a surfactant (e.g., sodium ligninsulfonate and polyoxyethylene fatty alcohol ether), and 0.1-2% by weight of a thickener (e.g., modified clay, especially BENTONE® or silica) and an organic carrier are added 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 yields a stable dispersion of the active substance.

[0294] vi) Water-dispersible granules and water-soluble granules (WG, SG) At least one compound of formula (I) in an amount of 50-80% by weight is pulverized with the addition of a surfactant (e.g., sodium ligninsulfonate and polyoxyethylene fatty alcohol ether) and converted into water-dispersible or water-soluble granules by technical equipment (e.g., extruder, spray tower, fluidized bed). The surfactant is used in an amount such that the total amount is 100% by weight. Dilution with water yields a stable dispersion or solution of the active substance.

[0295] vii) Water-dispersible powders 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 similar amount of a solid support, such as silica gel, and ground in a rotor stator mill until the total amount is 100% by weight. Dilution with water yields a stable dispersion or solution of the active substance.

[0296] viii) Gel (GW, GF) In a stirred ball mill, 5-25% by weight of at least one compound of formula (I) is added to 3-10% by weight of a surfactant (e.g., sodium ligninsulfonate) and ground, and then 1-5% by weight of a binder (e.g., carboxymethylcellulose) and an equal amount of water are added to make a total volume of 100% by weight. This yields a fine suspension of the active substance. Dilution with water yields a stable suspension of the active substance.

[0297] ix) Microemulsion (ME) Add 5-20% by weight of at least one compound of formula (I) 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 such amounts of water to a total volume of 100% by weight. Stir this mixture for 1 hour to spontaneously generate a thermodynamically stable microemulsion.

[0298] 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) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Radical polymerization initiated by a radical initiator forms poly(meth)acrylate microcapsules. Alternatively, an oil phase containing 5-50% by weight of at least one compound of formula (I), 0-40% by weight of a water-insoluble organic solvent (e.g., aromatic hydrocarbon), and an isocyanate monomer (e.g., diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g., polyvinyl alcohol). Addition of a polyamine (e.g., hexamethylenediamine) forms polyurea microcapsules. This monomer reaches 1-10% by weight of the total CS composition.

[0299] xi) Powder formulations (DP, DS) At least one compound of formula (I) in an amount of 1 to 10% by weight is finely ground and tightly mixed with such an amount of a solid carrier, for example, finely divided kaolin, so that the total amount is 100% by weight.

[0300] xii) Granules (GR, FG) At least one compound of formula (I) is finely ground in an amount of 0.5 to 30% by weight and combined with such an amount of a solid carrier (e.g., silicate) to a total amount of 100% by weight. Granulation is achieved by extrusion, spray drying, or fluidized bed.

[0301] xiii) Ultra-trace liquid (UL) Dissolve 1 to 50% by weight of at least one compound of formula (I) in such an amount of organic solvent, for example, an aromatic hydrocarbon, until the total amount is 100% by weight.

[0302] Compositions of type i) to xiii) may optionally contain 0.1 to 1% by weight of an additive 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.

[0303] Mixture / combination The compounds of formula (I) and the compositions of the present invention can be mixed with other active ingredients such as fungicides, fungicides, acaricides, nematicides, insecticides, biological control agents, or herbicides. Mixing with fertilizers, growth regulators, safeners (phytotoxicity reducers), nitrification inhibitors, semiochemicals, and / or other agriculturally beneficial agents is also possible. This can broaden the activity spectrum or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides, and fungicides are disclosed in the Pesticide Manual (17th edition).

[0304] Examples of fungicides that can be mixed with the compound of formula (I) and the composition of the present invention are as follows: 1) Ergosterol biosynthesis inhibitors, e.g., (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxyconazole, (1.004) fenhexamide, (1.005) fenpropidine, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafole, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) Mycrobutanil, (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-triazole-1-ylmethyl)cyclopentanol, (1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazole-1-ylmethyl)cyclopentanol, (1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazole-1-yl)butan-2-ol, (1.029)(2R)-2-(1-chlorocyclopropyl) -4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazole-1-yl)butan-2-ol, (1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazole-1-yl)propan-2-ol, (1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazole-1-yl)butan-2-ol, (1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazole-1-yl)butan-2-ol, (1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazole-1-yl)propan-2-ol, (1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazole-4-yl](pyridine-3-yl) (L)methanol, (1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazole-4-yl](pyridine-3-yl)methanol, (1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazole-4-yl](pyridine-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-triazole-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl [(nyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole-5-ylthiocyanate, (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-thion, (1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044)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-thion, (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-thion, (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-thion, (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-thion, (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-thion, (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-triazole-1-yl)propan-2-ol, (1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazole-1-yl)butan-2-ol, (1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazole-1-yl)butan-2-ol, (1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazole-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-triazole-1-ylmethyl)cyclopentanol, (1.060)5-(allylsulfanil)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061)5-(allylsulfanil)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062)5-(allylsulfanil)- 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-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methyl Imidoformamide, (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-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-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-methylpyridine-3-yl]-N-ethyl-N-methylimidoformamide, (1.075)N'-{4-[(4,5-dichloro-1,3-thiazole-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076)N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridine-3-yl}-N-ethyl-N-methylimidoformamide, (1.077)N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridine-3-yl}-N-ethyl-N-methylimidoformamide, (1.078)N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridine-3-yl}-N-ethyl-N-methylimidoformamide, (1.079)N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridine-3-yl}-N-ethyl-N-methylimidoformamide, (1.080)N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridine-3-yl}-N-ethyl-N-methylimidoformamide, . (1.081) Ifentrifluconazole, (1.082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazole-1-yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)pro Pan-2-ol, (1.084)2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol, (1.085)3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-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-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, (1.087)N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylimidoformamide, (1.088)N'-{5- Bromo-2-methyl-6-[(1-propoxypropan-2-yl)oxy]pyridine-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-triazole-1-yl)propanoate.

[0305] 2) Inhibitors of the respiratory chain of complex I or II, e.g., (2.001) benzovindiflupir, (2.002) bixafen, (2.003) boscalid, (2.004) carboxyne, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapiroxad, (2.008) flametopyr, (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 (a mixture of syn epimara semiforms 1RS,4SR,9RS and anti epimara semiforms 1RS,4SR,9SR), (2.014) Isopyrazam (syn epimer enantiomers 1R,4S,9R), (2.015) Isopyrazam (syn epimer enantiomers 1S,4R,9S), (2.016) Isopyrazam (syn epimer enantiomers (1RS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pidiflumetofen, (2.020) Pyraziflumid, (2.021) Sedaxane, (2.022) 1,3-Dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-Dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide Boxamide, (2.024)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025)1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028)Impyrfluxam, (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-Flu Oro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridine-2-yl]oxy}phenyl)ethyl]quinazoline -4-amine, (2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5- Luoro-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-methanonaphthalene-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalene-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-(difluoro Methyl)-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)-1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-Cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-Cyclopropyl-N-(2-Cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide Thamide, (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) Pyapropoine, (2.058) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059) N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.060) Fluveneteram.

[0306] 3) Inhibitors of the respiratory chain of complex III, e.g., (3.001) ametoctrazine, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamide, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) phenamidone, (3.011) fluphenoxystrobin, (3.012) Fluoxastrobin, (3.013) Cresoximmethyl, (3.014) Metminostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyramethostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}fe [(Iyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazole-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpento-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} (3.025) Fenpicoxamide, (3.026) Mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamide-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazole-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) Methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazole-1-yl]-2-methylbenzyl}carbamate, (3.030) Methyltetraprole, (3.031) Florylpicoxamide, (3.032)(2S,3S)-3-(o-tolyl)butan-2-yl N-{[4-methoxy-3-(propanoyloxy)-2-pyridyl]carbonyl}-L-alaninate.

[0307] 4) Inhibitors of mitosis and cell division, e.g., (4.001) carbendazim, (4.002) diethofencarb, (4.003) etaboxam, (4.004) fluopicolide, (4.005) pencyclon, (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- (Iyl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazole-5-amine (4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6- (Difluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.(022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.026) fluopimomide.

[0308] 5) Compounds capable of multi-site action, for example, (5.001) Bordeaux mixture, (5.002) Captahole, (5.003) Captan, (5.004) Chlorothalonyl, (5.005) Copper hydroxide, (5.006) Copper naphthenate, (5.007) Copper oxide, (5.008) Copper oxychloride, (5.009) Copper(II) sulfate, (5.010) Dithianone, (5.011 ) Dozin, (5.012) Holpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Methylam, (5.016) Methylam 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.

[0309] 6) Compounds that can induce host defense, e.g., (6.001) acibenzoral-S-methyl, (6.002) isothianil, (6.003) probenazole, (6.004) thiadinil.

[0310] 7) Inhibitors of amino acid and / or protein biosynthesis, e.g., (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-dihydroisoquinoline-1-yl)quinoline.

[0311] 8) Inhibitors of ATP production, e.g., (8.001) silthiofam.

[0312] 9) Inhibitors of cell wall synthesis, e.g., (9.001) benciavaricarb, (9.002) dimethomorph, (9.003) fulmorph, (9.004) iprovalicarb, (9.005) mandipropamide, (9.006) pyrimorph, (9.007) valifenarate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridine-4-yl)-1-(morpholine-4-yl)propa-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridine-4-yl)-1-(morpholine-4-yl)propa-2-en-1-one.

[0313] 10) Inhibitors of lipid and membrane synthesis, e.g., (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclophosmethyl.

[0314] 11) Inhibitors of melanin biosynthesis, e.g., (11.001) trichillazole, (11.002) tolprocarb.

[0315] 12) Inhibitors of nucleic acid synthesis, e.g., (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mephenoxam).

[0316] 13) Inhibitors of signal transduction, e.g., (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxifen, (13.006) vinclozoline.

[0317] 14) Compounds that can act as uncouplers, e.g., (14.001) fluazinam, (14.002) meptyldinocap.

[0318] 15) (15.001) Abscisic acid, (15.002) Benciazole, (15.003) Bethoxazine, (15.004) Capsimycin, (15.005) Carvone, (15.006) Quinomethionate, (15.007) Cufraneb, (15.008) Cyflufenaamide, (15.009) Cymoxanil, (15.010) Cyprosulfamide, (15.011) Fluthianil, (15.012) Fosetyl aluminum, (15.013) Fosetyl calcium, (15.014) Fosetyl sodium, (15. 015) Methyl isothiocyanate, (15.016) Metraphenone, (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, (15.027) pyrophenone (crazaphenone), (15.028) tebufloquine, (15.029) tecrophthalam, (15.030) torniphanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazole-3-yl]-1,3-thiazole-2-yl}piperidine-1-yl (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazole-3-yl]-1,3-thiazole-2-yl}piperidine-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]etanone, (15.033) 2-(6-benzylpyridine-2-yl)quinazoline, (15.034) dipimethicone, (15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]-1-[4-(4-{5-[2-(propa-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazole-3-yl}-1,3-thiazole-2-yl)piperidine-1-yl]ethanone, (15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]-1-[4-(4-{5-[2-chloro-6-(propa-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazole-3-yl}-1,3 (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridine-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1 -{[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidine-4-yl)-1,3-thiazole-4-yl]-4,5-dihydro-1,2-oxazole-5-yl}-3-chlorophenylmethanesulfonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidine-4-yl)-1,3-thiazole-4-yl]-4,5-dihydro-1,2-oxazole-5-yl}-3-chlorophenylmethanesulfonate, (15 .041) Ipfluphenoquine, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinoline-3-yl)oxy]phenyl}propan-2-ol, (15.043) Fluoxapiproline, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidine-4-yl)-1,3-thiazole-4-yl]-4,5-dihydro-1,2-oxazole-5-yl}phenylmethanesulfonate, (15.045) 2-phenylphenol and salts, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)quinoline, (15.047)quinohumerine, (15.048)4-amino-5-fluoropyrimidine-2-ol (tautomer: 4-amino-5-fluoropyrimidine-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- Lolo-N'-phenyl-N'-(propa-2-in-1-yl)thiophene-2-sulfonohydrazide, (15.052)5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidine-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinoline-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055)buto-3-in-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-yl}carbamate, (15.056)ethyl(2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058)propyl 3,4,5-trihydroxybenzoate, (15.059)quinoline-8-ol, (15.060)quinoline-8-ol sulfate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridine-2-yl}carbamate, (15.062)5-fluoro-4-imino-3-methyl-1-[(4- [methylphenyl)sulfonyl]-3,4-dihydropyrimidine-2(1H)-one, (15.063)aminopyriphen, (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-methylquinoline-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (15.067)(5-bromo-1-(5,6-dimethylpyridine-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068)(3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridine-7-yl)quinoline), (15.069)(1-(4,5-dimethyl-1H-benzimidazole-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline) (15.070) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)quinolone, (15.071) 8-fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl)quinolone, (15.072) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)-8-fluoroquinoline, (15.073) (N-methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide), (15.074) methyl {4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl}carbamate, (15.075)(N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzyl}cyclopropanecarboxamide), (15.076)N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, . (15.077) N-[(E)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]benzamide, (15.078) N-[(Z)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]benzamide, (15.079) N-[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]cyclopropanecarboxamide, (15.080) N-(2-fluorophenyl)-4-[5-(triflu Oromethyl)-1,2,4-Oxadiazole-3-yl]benzamide, (15.081)2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]acetamide, (15.082)N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl)phenyl]methyl]acetamide, (15.083)N-[(E)-N-methoxy-C-methyl-carbonimidoyl]-4-(5-(trifluoromethyl)-1,2,4- Oxadiazole-3-yl]benzamide, (15.084)N-[(Z)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, (15.085)N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, (15.086)4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl] Pyrrolidine-2-one, (15.087)N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzenecarbothioamide, (15.088)5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrrolidine-2-one, (15.089)N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide, (15.(090) 1-Methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, (15.091) 1,1-diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide, (15.093) N-Methoxy-N-[[4-[5-(trifluoromethyl) -1,2,4-Oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094) 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl]urea, (15.095) N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazole-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096) N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4 -Oxadiazole-3-yl]phenyl]methyl]propanamide, (15.097)N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl)phenyl]methyl]propanamide, (15.098)1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, (15.099)1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl ]phenyl]methyl]urea, (15.100)3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea, (15.101)1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]piperidine-2-one, (15.102)4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, (15.103) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, (15.104) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]piperidine-2-one, (15.105) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadi Azole-3-yl]phenyl]methyl]azepan-2-one, (15.106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one, (15.108) ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzyl}-1H-pyrazole-4-carboxylate, (15.109)N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzyl}-1H-1,2,4-triazole-3-amine, (15.110)N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzyl}butanamide, (15.111)N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide (15.112)N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide, (15.113)1-(5,6-dimethylpyridine-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114)1-(6-(difluoromethyl)-5-methylpyridine-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115)1-(5-(fluoromethyl)-6-methylpyridine-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116)1-(6-(difluoromethyl)-5-methoxypyridine-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.117)4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyldimethylcarbamate, (15.118)N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl}propanamide, (15.119)3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidine-4-yl)-1,3-thiazole-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl Methanesulfonate, (15.120)9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidine-4-yl)-1,3-thiazole-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-ylmethanesulfonate, (15.121)3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidine-4-yl)-1,3-thiazole-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl Methanesulfonate, (15,122)3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazole-1-yl]acetyl}piperidine-4-yl)-1,3-thiazole-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-yl Methanesulfonate, (15.123) 1-(6,7-dimethylpyrazolo[1,5-a]pyridine-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.124) 8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide, (15.125) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15.126) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide, (15.Further fungicides selected from the group consisting of (127) N-[(2S)-2,4-dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide and (15.128) D-tagatose.

[0319] All named mixed partners of the above classes (1) to (15) may exist in the form of free compounds or, where their functional groups enable, in the form of their pesticide-activated salts.

[0320] The compound of formula (I) and the compositions of the present invention may also be combined with one or more biological control agents.

[0321] As used herein, the term “biological control” is defined as the control of plant pathogenic fungi and / or insects and / or mites and / or nematodes and other pests by the use or adoption of biological control agents.

[0322] 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 organism for biological control. Mutants of the second organism are included in the definition of a biological control agent. The term “mutant” refers to a variant of a parent plant, as well as methods for obtaining a mutant or variant whose insecticidal activity is greater than that expressed by the parent plant. “Parent plant” is defined herein as the original strain before mutagenesis. To obtain such a mutant, the parent plant may be thoroughly treated with chemicals such as N-methyl-N'-nitro-N-nitrosoguanidine, ethylmethanesulfone, or by irradiation using gamma rays, X-rays, or UV irradiation, or by other means well known to those skilled in the art. Known mechanisms of biological control agents include enterobacteria that control root rot by defeating fungi by seeking 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 toxins in situ.

[0323] A "variant" is a strain that possesses all the distinctive characteristics of the NRRL or ATCC accession number as described in this specification, and can be identified as having a genome that hybridizes to the NRRL or ATCC accession number genome under high stringency conditions.

[0324] Hybridization refers to a reaction in which one or more polynucleotides react to form a complex that is stabilized via hydrogen bonds between the bases of nucleotide residues. Hydrogen bonds can occur in Watson-Crick base pairings, Hoogstein bonds, or other sequence-specific ways. The complex may consist of two chains forming a double-stranded structure, three or more chains forming a polychain complex, a single self-hybridized chain, or any combination thereof. Hybridization reactions can be carried out under various "stringency" conditions. Generally, low-stringency hybridization reactions are carried out at about 40°C in a solution of 10 × SSC or equivalent ionic strength / temperature. Moderate-stringency hybridization reactions are typically carried out at about 50°C with 6 × SSC, and high-stringency hybridization reactions are generally carried out at about 60°C with 1 × SSC.

[0325] A variant of an NRRL or ATCC accession number may also be defined as a strain having a genomic sequence having more than 85%, more preferably more than 90%, or more preferably more than 95% sequence identity with respect to the genome of the 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” with respect to another sequence means that, when aligned, the percentage of its bases (or amino acids) is identical when comparing the two sequences. This alignment and percentage homology or sequence identity can be determined using software programs known in the art, such as those described in “Current Protocols in Molecular Biology” (FM Ausubel et al., eds., 1987).

[0326] "NRRL" is an abbreviation for "Agricultural Research Service Culture Collection," an international depositary organization for the purpose of depositing microbial strains under the Budapest Convention on the International Recognition of the Deposit of Microorganisms for Patent Proceedings. It is located at 1815 North University Street, Peroira, Illinois, USA (zip code 61604), within the Agricultural Research Service, National Center for Agricultural Utilization Research, U.S. Department of Agriculture.

[0327] "ATCC" is an abbreviation for "American Type Culture Collection," an international depositary organization for the purpose of depositing microbial strains under the Budapest Convention for the International Recognition of the Deposit of Microorganisms for Patent Proceedings. Its address is 10801 University Boulevard, Manassas, Virginia, USA (zip code 10110), and it is known as the ATCC Patent Depository.

[0328] Examples of biological control agents that can be combined with the compound of formula (I) and the composition of the present invention are as follows: (A) Antimicrobial agents selected from the following group: (A1) For example, the following bacteria: (A1.1) Bacillus subtilis, in particular 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 strain D747 (available as DOUBLE NICKEL®), accession number FERM BP-8234, U.S. Patent No. 7,094,592; (A1.3) Bacillus pumilus, in particular BU (A1.4) Bacillus subtilis var. amyloliquefaciens FZB24 strain, accession number DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5)); (A1.5) Paenibacillus species strain, accession number NRRL B-50972 or NRRL B-67129, International Publication No. 2016 / 154297; (A1.6) Bacillus subtilis BU1814 strain (BASF Available from SE Corporation as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA; (A1.7) Bacillus mojavensis® 3(A1.8) B strain (accession number NCAIM(P)B001389) (International Publication No. 2013 / 034938), Certis USA, a subsidiary of Mitsui & Co.; (A1.9) Paenibacillus polymyxa, in particular strain AC-1 (e.g., TOPSEED®, Green Biotech Company); (A1.10) Pseudomonas proradix (e.g., PRORADIX®, Sourcon Padena); (A1.11) Pantoea agglomerans, in particular strain E325 (accession number NRRL B-21856) (BLOOMTIME, Northwest Agri Products) Available as BIOLOGICAL(trademark)FD BIOPESTICIDE); and (A2) For example, the following fungi: (A2.1) Aureobasidium pullulans, in particular budding spores of strain DSM14940, budding spores of strain DSM14941, or mixtures of budding spores of strains DSM14940 and DSM14941 (e.g., BOTECTOR® and BLOSSOM PROTECT® from bio-ferm GmbH, Switzerland); (A2.2) Pseudozyma aphidis (disclosed in International Publication No. 2011 / 151819 by Yissum Research Development Company, Hebrew University, Jerusalem); (A2.3) Certain species of Saccharomyces cerevisiae, Lesaffre et al., France Compagnie's CNCM numbers I-3936, I-3937, I-3938, or I-3939 (International Publication No. 2010 / 086790); (B) A biofungicide selected from the following group: (B1) For example, the following bacteria: (B1.1) Bacillus subtilis, in particular strain QST713 / AQ713 (available from Bayer CropScience (USA) as SERENADE OPTI or SERENADE ASO, NRRL accession number B21661, and U.S. Patent No. 6,060,051); (B1.2) Bacillus pumilus, in particular strain QST2808 (available from Bayer CropScience (USA) as SONATA®, accession number NRRL B-30087, and U.S. Patent No. 6,245,551); (B1.3) Bacillus pumilus, in particular strain GB34 (available from Bayer (Germany) as Yield Shield®); (B1.4) Bacillus pumilus (B1.5) Bacillus pumilus), in particular strain BU F-33, NRRL accession number 50185 (available from BASF as a CARTISSA product, EPA registration number 71840-19); (B1.6) Bacillus amyloliquefaciens, in particular strain D747 (available from Kumiai Chemical Industries as Double Nickel®, accession number FERM BP-8234, U.S. Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan as BIOBAC® WP, registered in Taiwan as a biocide under registration numbers 4764, 5454, 5096, and 5277); (B1.7) Bacillus subtilis MBI 600 strain (BASF (Available from SE Corporation as SUBTILEX), accession number NRRL B-50595, U.S. Patent No. 5,061,495; (B1.8) Bacillus subtilis strain GB03 (available from Bayer GmbH in Germany as Kodiak®); (B1.9) Bacillus amyloriquefaciens (variety) (Bacillus subtilis var.(B1.10) Bacillus mycoides J isolate, accession number B-30890 (available from Certis USA, a subsidiary of Mitsui & Co., as BMJ TGAI® or WG and LifeGard®); (B1.11) Bacillus licheniformis, particularly strain SB3086, accession number ATCC 55406, international publication 2003 / 000051 (available from Certis USA, a subsidiary of Mitsui & Co., as ECOGUARD® Biofungicide and GREEN (B1.12) Paenibacillus species strain, accession number NRRL B-50972 or NRRL B-67129, International Publication No. 2016 / 154297; (B1.13) Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX, and VELONDIS® EXTRA); (B1.14) Bacillus subtilis CX-9060, Certis USA, a subsidiary of Mitsui & Co.; (B1.15) Bacillus amyloriquefaciens Bacillus amyloliquefaciens) F727 strain (also known as MBI110 strain) (NRRL accession number B-50768, International Publication No. 2014 / 028521) (STARGUS® registered trademark of Marrone Bio Innovations); (B1.16) Bacillus amyloliquefaciens FZB42, accession number DSM 23117 (available as RHIZOVITAL® registered trademark from ABiTEP GmbH in Germany); (B1.17) Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (QUARTZO® (WG) and PRESENCE® of FMC Corporation); (B1.18) Bacillus mojavensis R. 3 (B1.19) Paenibacillus polymyxa ssp. plantarum (International Publication No. 2016 / 020371), Certis USA, a subsidiary of Mitsui & Co.; (B1.20) Paenibacillus epiphyticus (International Publication No. 2016 / 020371), BASF SE; (B1.21) Pseudomonas chlororaphis AFS009 strain, accession number NRRL B-50897, International Publication No. 2017 / 019448, (e.g., AgBiome, USA) HOWLER® and ZIO® (trademarks) of Innovations Inc.; (B1.22) Pseudomonas chlororaphis, in particular strain MA342 (e.g., CEDOMON®, CERALL®, and CEDRESS® by Bioagri and Koppert); (B1.23) Streptomyces lydicus WYEC 108(Streptomyces lydicus (also known as WYCD108US strain) (Acti-Iron® and Actinovate® registered trademarks of Novozymes); (B1.24) Agrobacterium radiobacter K84 strain (e.g., Galltrol-A® registered trademark of AgBioChem, Canada); (B1.25) Agrobacterium radiobacter K1026 strain (e.g., NOGALL® trademark of BASF SE); (B1.26) Bacillus subtilis KTSB strain (FOLIACTIVE® registered trademark of Donaghys); (B1.27) Bacillus subtilis IAB / BS03 (STK Bio-Ag AVIV (trademark) of Technologies); (B1.28) Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan as BIOBAC (registered trademark) WP, registered in Taiwan as a biofungicide under registration numbers 4764, 5454, 5096, and 5277); (B1.29) Bacillus amyloliquefaciens B246 isolated strain (e.g., AVOGREEN (trademark) of the University of Pretoria); (B1.30) Bacillus methylotrophicus strain BAC-9912 (Chinese Academy of Sciences' Institute of Applied Ecology); (B1.31) Pseudomonas proradix (e.g., Sourcon PRORADIX (registered trademark) of Padena Corporation); (B1.32) Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (accession number DSM 7206) (see Verdera's MYCOSTOP®, BioWorks' PREFENCE®, Crop Protection 2006, 25, 468-475); (B1.33) Pseudomonas fluorescens strain A506 (e.g., NuFarm's BLIGHTBAN®); and. (B2) Fungi, such as the following: (B2.1) Coniothyrium minitans, in particular strain CON / M / 91-8 (accession number DSM-9660, e.g., Contans® registered trademark of Bayer CropScience Biologics GmbH); (B2.2) Metschnikowia fructicola, in particular strain NRRL Y-30752; (B2.3) Microsphaeropsis ochracea; (B2.5) Trichoderma atroviride, in particular strain SC1 (accession number CBS 122089, International Publication No. 2009 / 116106 and U.S. Publication No. 8,431,120 (Bi-PA)), strain 77B (Andermatt (B2.6) Trichoderma harzianum strain T-22 (e.g., Andermatt Biocontrol or Koppert's Trianum-P) or Cepa Simb-T5 (Simbiose Agro); (B2.14) Gliocladium roseum (also known as Clonostachys rosea f. rosea), in particular strain 321U from Adjuvants Plus, 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): ACM941 strain or IK726 strain (Jensen DF, et al.) disclosed in 519-524.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 V117b strain; (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®, Kumiai Chemical Industry Co., Ltd.), strain T34 (e.g., Biocontrol, Spain) (B2.38) Trichoderma atroviride strain V08 / 002387 (e.g., Esquive® WP from Agrauxine, France); (B2.39) Trichoderma atroviride strain V08 / 002387; (B2.40) Trichoderma atroviride NMI strain V08 / 002388; (B2.41) Trichoderma atroviride NMI strain V08 / 002389; (B2.42) Trichoderma atroviride Trichoderma atroviride (LC.) NMI strain V08 / 002390; (B2.43) 52(e.g., Tenet from Agrimm Technologies); (B2.44) Trichoderma atroviride ATCC strain 20476 (IMI 206040); (B2.45) Trichoderma atroviride T11 strain (IMI 352941 / CECT 20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g., Trichodex® from Makhteshim in the US); (B2.49) Trichoderma asperelum (B2.50) Trichoderma harzianum strain ITEM908 (e.g., Trianum-P from Andermatt Biocontrol); (B2.51) Trichoderma harzianum strain TH35 (e.g., Root-Pro from Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens), particularly GL-21 (e.g., SoilGard from Certis, USA); (B2.53) Trichoderma viride strain TV1 (e.g., Trianum-P from Koppert); (B2.54) Ampelomyces quisquaris (quisqualis), in particular strain AQ 10 (e.g., AQ 10 (registered trademark) from IntrachemBio, Italy); (B2.56) Aureobasidium pullulans, in particular budding spores of strain DSM14940; (B2.57) Aureobasidium pullulans, in particular budding spores of strain DSM 14941; (B2.58) Aureobasidium pullulans, particularly a mixture of budding spores of strains DSM14940 and DSM14941 (e.g., Botector® by bio-ferm, Switzerland); (B2.64) Cladosporium cladosporioides H39, accession number CBS122244, U.S. Patent Application Publication No. 2010 / 0291039 (by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulata) (B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii) KV01 strain of conidia (e.g., Vertalec® strain by Koppert / Arysta); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, WRL-076 strain (NRRL Y-30842), U.S. Patent No. 7,579,183; (B2.75) Trichoderma atroviride, SKT-1 strain (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 Trichoderma viride), ICC.080 (B2.79) Trichoderma harzianum strain (IMI CC392151 CABI, e.g., BioDerma by AGROBIOSOL DE MEXICO); (B2.80) Trichoderma polysporum strain IMI 206039 (e.g., Binab TF WP by BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum, accession number Ts3550 (e.g., Tricovab by CEPLAC, Brazil); (B2.83) Ulocladium oudemansii strain U3, accession number NM 99 / 06216 (e.g., BOTRY-ZEN® by Botry-Zen of New Zealand and BOTRYSTOP® by BioWorks); (B2.84) Verticillium albo-atrum (formerly known as Verticillium dahliae), WCS850 strain, accession number WCS850, deposited with the Central Bureau for Fungi Cultures (e.g., DUTCH TRIG® by Tree Care Innovations); (B2.86) Verticillium chlamydosporium; (B2.87) Trichoderma asperellum ICC 012 strain (Trichoderma harzianum ICC 012 (also publicly known), accession number (B2.88) A mixture of CABI CC IMI 392716 and Trichoderma gamsii (formerly known as Trichoderma viride) ICC 080, accession number IMI 392151 (e.g., BIO-TAM® from Isagro USA and BIODERMA® from Agrobiosol de Mexico); (B2.89) Trichoderma asperelloides JM41R (accession number NRRL B-50759) (TRICHO PLUS® from BASF SE); (B2.89) Aspergillus flavus NRRL 21882 strain (also known as AFLA-GUARD® from Syngenta / ChemChina); (B2.90) Chaetomium cupreum (B2.91) Saccharomyces cerevisiae, in particular, the cell wall of strain LASO2 (Agro-Levures et De'rive's), strain LAS117 (CEREVISANE® of Lesaffre, ROMEO® of BASF SE), strains CNCM I-3936, I-3937, I-3938, and I-3939 of Lesaffre et Compagnie, France (International Publication No. 2010 / 086790); (B2.92) Trichoderma viren G-41 strain, formerly known as Gliocladium virens Known as *Virens* (accession number ATCC20906) (e.g., BioWorks in the United States, ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP); (B2.93) *Trichoderma hamatum*, accession number ATCC28012; (B2.94) Ampelomyces quisqualis AQ10 strain, accession number CNCM I-807 (e.g., AQ 10® registered trademark of IntrachemBio, Italy); (B2.95) Phlebiopsis gigantea VRA 1992 strain (ROTSTOP® registered trademark of Danstar Ferment); (B2.96) Penicillium steckii (DSM 27859, International Publication No. 2015 / 067800), BASF SE; (B2.97) Chaetomium globosum (known as RIVADIOM® registered trademark by Rivale); (B2.98) Cryptococcus flavesens (B2.99) Dactylaria candida (B2.100) Dilophosphora alopecuri (available as TWIST FUNGUS®); (B2.101) Fusarium oxysporum Fo47 (available as FUSACLEAN® by Natural Plant Protection); (B2.102) Pseudozyma flocculosa PF-A22 UL (available as SPORODEX® by Plant Products, Canada); (B2.103) Trichoderma gamsii (formerly known as Trichoderma viride), ICC 080 (IMI CC392151 CABI) (Available as BIODERMA (registered trademark) from AGROBIOSOL DE MEXICO); (B2.104) Trichoderma fertile (e.g., BASF's TrichoPlus product); (B2.105) Muscodor roseus, in particular strain A3-5 (accession number NRRL 30548); (B2.106) Simplicillium lanosoniveum; A biological control agent having an effect of improving plant growth and / or plant health, which can be combined in combination of compounds according to the present invention, including the following: (C1) Bacteria selected from the group consisting of Bacillus pumilus, in particular strain QST2808 (accession number: NRRL number B-30087); Bacillus subtilis, in particular strain QST713 / AQ713 (with NRRL accession number B-21661, described in U.S. Patent No. 6,060,051, available from Bayer CropScience, Inc. in the United States as SERENADE® OPTI or SERENADE®); Bacillus subtilis, in particular strain AQ30002 (with accession number NRRL B-50421, described in U.S. Patent Application Publication No. 13 / 330,576); Bacillus subtilis, in particular strain AQ30004 (and NRRL B-50455, as described in U.S. Patent Application Publication No. 13 / 330,576); Sinorhizobium meliloti NRG-185-1 strain (NITRAGIN®, Bayer Crop Science); Bacillus subtilis BU1814 strain (TEQUALIS®, BASF SE); Bacillus subtilis rm303 (RHIZOMAX®, Biofilm Crop Protection); Bacillus amyloliquefaciens pm414 (LOLI-PEPTA®, Biofilm Crop Protection);Bacillus mycoides BT155 (NRRL number B-50921), Bacillus mycoides EE118 (NRRL number B-50918), Bacillus mycoides EE141 (NRRL number B-50916), Bacillus mycoides BT46-3 (NRRL number B-50922), Bacillus cereus family member EE128 (NRRL number B-50917), Bacillus thuringiensis BT013A (NRRL number B-50924) (Bacillus thuringiensis (Bacillus Bacillus thuringiensis (also known as 4Q7), Bacillus cereus family member EE349 (NRRL number B-50928), Bacillus amyloliquefaciens SB3281 (ATCC number PTA-7542, International Publication No. 2017 / 205258), Bacillus amyloliquefaciens TJ1000 (available from Novozymes as QUIKROOTS®); Bacillus firmus, in particular strain CNMC I-1582 (e.g., VOTIVO® from BASF SE); Bacillus pumilus, in particular strain GB34 (e.g., YIELD from Bayer Crop Science, Germany). SHIELD (registered trademark); Bacillus amyloliquefaciens, in particular strain IN937a; Bacillus amyloliquefaciens, in particular strain FZB42 (e.g., RHIZOVITAL (registered trademark) 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 strain BP01 (ATCC 55675, e.g., MEPICHLOR® from Arysta Lifescience, USA); Bacillus subtilis, in particular strain MBI 600 (e.g., SUBTILEX® from BASF SE); Bradyrhizobium japonicum (e.g., OPTIMIZE® from Novozymes); Mesorhizobium cicer (e.g., BASF SE's NODULATOR; Rhizobium leguminosarium biovar viciae (e.g., BASF SE's NODULATOR); Delftia acidovorans, especially strain RAY209 (e.g., Brett Young Seeds' BIOBOOST®); Lactobacillus species (e.g., LACTOPLANT® from LactoPAFI); Paenibacillus polymyxa, especially strain AC-1 (e.g., Green Biotech Company's TOPSEED®); Pseudomonas proradix (e.g., Sourcon Padena's PRORADIX®); Azospirillum brasiliensis (e.g., VIGOR® by KALO); Azospirillum lipoferum (e.g., VERTEX-IF® by TerraMax);A mixture of Azotobacter vinelandii and Clostridium pasteurianum (available as INVIGORATE® from Agrinos); Pseudomonas aeruginosa, especially strain PN1; Rhizobium leguminosarum, especially strain (bv. viceae) Z25 (accession number CECT 4585); Azorhizobium caulinodans, especially strain ZB-SK-5; Azotobacter chroococcum, especially strain H23; Azotobacter vinelandii *Bacillus vinelandii*, in particular strain ATCC12837; *Bacillus siamensis*, in particular strain KCTC13613T; *Bacillus tequilensis*, in particular strain NII-0943; *Serratia marcescens*, in particular strain SRM (accession number MTCC8708); *Thiobacillus* species (e.g., CROPAID® from Cropaid, UK); and; (C2) Fungi selected from the group consisting of 251 strains of Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus) (AGAL 89 / 030550, e.g., BioAct by Bayer CropScience Biologics GmbH), Penicillium bilaii ATCC22348 strain (e.g., JumpStart® by Acceleron BioAg), and Talaromyces flavus V117b strain; Trichoderma atroviride strain CNCM I-1237 (e.g., Esquive® WP by Agrauxine, France); Trichoderma viride, e.g., strain B35 (Pietr et al., 1993, Zesz. Nauk. AR w Szczecinie 161: 125-137); Trichoderma atroviride LC 52(Also known as Trichoderma atroviride LU132 strain, e.g., Sentinel from Agrimm Technologies); Trichoderma atroviride SC1 strain, described in international application PCT / IT2008 / 000196; Trichoderma asperellum kd strain (e.g., T-Gro from Andermatt Biocontrol); Trichoderma asperellum Eco-T strain (Plant Health Products, South Africa); Trichoderma harzianum T-22 strain (e.g., Trianum-P from Andermatt Biocontrol or Koppert); Myrothecium verrucaria AARC-0255 strain (e.g., Valent Biosciences' DiTera (trademark); Penicillium bilaii ATCC ATCC 20851Strains; Pythium oligandrum M1 strain (ATCC38472, e.g., Polyversum from Bioprepraty, Czech Republic); Trichoderma virens GL-21 strain (e.g., SoilGard® from Certis, USA); Verticillium albo-atrum (formerly V. dahliae) WCS850 strain (CBS 276.92, e.g., Dutch Trig from Tree Care Innovations); Trichoderma atroviride atroviride), in particular strain V08 / 002387, NMI number V08 / 002388, NMI number V08 / 002389, NMI number V08 / 002390; Trichoderma harzianum ITEM 908; Trichoderma harzianum TSTh20; Trichoderma harzianum 1295-22; Pythium oligandrum DV74; Rhizopogon amylopogon (for example, contained in Myco-Sol from Helena Chemical Company); Rhizopogon fulvigleba (for example, contained in Helena Chemical Included in Myco-Sol of Company; and Trichoderma virens GI-3 strain; Select from the following insecticidal biological control agents: (D1) Bacteria selected from the following group: Bacillus thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372, e.g., XENTARI® from Valent BioSciences); Bacillus mycoides, J isolate (e.g., BmJ from Certis USA, a subsidiary of Mitsui & Co.); Bacillus sphaericus, in particular serotype H5a5b, strain 2362 (ABTS-1743) (e.g., VECTOLEX® from Valent BioSciences in the United States); Bacillus thuringiensis subsp. kurstaki, BMP strain 123, Becker Microbial, Israel Products Inc.; Bacillus thuringiensis subsp. aizawai, especially celotype H-7 (e.g., FLORBAC®, a registered trademark of Valent BioSciences, USA); Bacillus thuringiensis subsp. kurstaki HD-1 strain (e.g., DIPEL®, a registered trademark of Valent BioSciences, USA); Bacillus thuringiensis subsp. kurstakikurstaki) BMP 123 strain, Becker Microbial Products, Israel; Bacillus thuringiensis israelensis BMP 144 strain (e.g., AQUABAC® by Becker Microbial Products, Israel); Burkholderia species, in particular Burkholderia rinojensis A396 strain (also known as Burkholderia rinojensis MBI strain) (accession number NRRL B-50319, international publications 2011 / 106491 and 2013 / 032693, e.g., MBI-206 by Marrone Bio Innovations) TGAI and ZELTO®); Chromobacterium subtsugae, in particular, strain PRAA4-1T (MBI-203, e.g., GRANDEVO® from Marrone Bio Innovations); Paenibacillus popilliae (formerly known as Bacillus popilliae), e.g., MILKY SPORE POWDER® and MILKY SPORE GRANULAR® from St. Gabriel Laboratories); Bacillus thuringiensis subsp. israelensis (Cerotype H-14) AM65-52 strain (Accession number ATCC1276) (e.g., Valent, USA) VECTOBAC® from BioSciences); Bacillus thuringiensis var. kurstaki EVB-113-19 strain (e.g., BIOPROTEC® from AEF Global); Bacillus thuringiensis subsp. tenebryonisBacillus tenebrionis)NB 176 plants (SD-5428, for example, NOVODOR® from BioFa, Germany); Bacillus thuringiensis var. japonensis Buibui plant; Bacillus thuringiensis subsp. kurstaki) ABTS 351 plants; Bacillus thuringiensis subsp. kurstaki) PB 54 plants; Bacillus thuringiensis subsp. kurstaki) SA 11 plants; Bacillus thuringiensis subsp. kurstaki) SA 12 strains; Bacillus thuringiensis subsp. kurstaki EG 2348 strain; Bacillus thuringiensis var. Colmeri (e.g., TIANBAOBTC by Changzhou Jianghai Chemical Factory); Bacillus thuringiensis subsp. aizawai GC-91 strain; Serratia entomophila (e.g., INVADE® by Wrightson Seeds); Serratia marcescens, in particular, SRM strain (accession number MTCC8708); and Wolbachia pipientis ZAP strain (e.g., ZAP by MosquitoMate) MALES (registered trademark); and. (D2) Fungi selected from the following group: Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) apopka 97 strains; Beauveria bassiana ATCC 74040 strains (e.g., NATURALIS® from Intrachem Bio, Italy); Beauveria bassiana GHA strain (accession number ATCC 74250 For example, Laverlam International Corporation's BOTANIGUARD® ES and MYCONTROL-O®; Zoohtora radicans; Metarhizium robertsii 15013-1 (deposited under NRRL accession number 67073), Metarhizium robertsii 23013-3 (deposited under NRRL accession number 67075), and Metarhizium anisopliae 3213-1 (deposited under NRRL accession number 67074) (International Publication No. 2017 / 066094, Pioneer Hi-Bred International); Beauveria bassiana ATP02 strain (accession number DSM 24665); Beauveria bassiana strain ATP02 (accession number DSM 24665). Among these, Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain apopka 97 is particularly preferred. (E) Viruses selected from the following group: Adoxophyes orana (summer fruit tortillus) granulosis virus (GV), Cydia pomonella (codlinga) granulosis virus (GV), Helicoverpa armigera (tobacco budworm larva) nuclear polyhedrosis virus (NPV), Spodoptera exigua (white-striped moth) mNPV, Spodoptera frugiperda (armyworm larva) mNPV, and Spodoptera littoralis (African cottony leafworm) NPV; (F) Bacteria and fungi that can be added to plants or parts of plants or organs of plants as “inoculants” and that promote plant growth and plant health by their specific properties. Examples include: species of the genera Agrobacterium, Azorhizobium caulinodans, Azospirillum, Azotobacter, Bradyrhizobium, Burkholderia, especially Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora or Gigaspora monosporum, Glomus, Laccaria, and Lactobacillus buchneri. buchneri), species of the genera Paraglomus, Pisolithus tinctorus, species of the genera Pseudomonas, species of the genera Rhizobium, especially Rhizobium trifolii, species of the genera Rhizopogon, species of Scleroderma, species of Suillus, and species of Streptomyces; 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 (pyrethrin), Cassia amara Quercus amara, Quercus genus, Quillaya, Regalia, "Requiem (trademark) insecticide", Rotenone, Liany / Ryanodine, Symphytum officinale, Tanacetum vulgare, Thymol, TRIACT (registered trademark) 70, TriCon, Tropeolum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract, especially rapeseed powder or mustard powder, and bioinsecticidal and acaricidal substances obtained from olive oil, especially as active ingredients with a carbon chain length of C 16 -C 20 Unsaturated fatty acids / carboxylic acids containing these, such as those found in products under the trade name FLiPPER®.

[0329] The compound of formula (I) and the compositions of the present invention can be combined with one or more active ingredients selected from insecticides, acaricides, and nematicides.

[0330] The terms “insecticide” and “insecticidal” refer to a substance’s ability to increase the mortality rate or inhibit the growth rate of insects. As used herein, the term “insect” includes all organisms of the class “Insecta.”

[0331] "Nematicidal" and "nematicidal" refer to a substance's ability to increase the mortality rate of nematodes or inhibit their growth rate. Generally, the term "nematode" includes the eggs, larvae, juveniles, and mature forms of the organism.

[0332] "Acaricide" and "acaricidal properties" refer to the ability of a substance to increase the mortality rate or inhibit the growth rate of ectoparasites belonging to the class Arachnida and subclass Mites.

[0333] Examples of insecticides, acaricides, and nematicides that can be mixed with the compound of formula (I) and the composition of the present invention are as follows: (1) Acetylcholinesterase (AChE) inhibitors, e.g., carbamates, e.g., alanicarb, aldicarb, bengiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, phenobucarb, formethaneate, furathiocarb, isoprocarb, methiocarb, methomyl, metholcarb, oxamyl, pyrimicarb, propoxul, thiodicarb, thiophanox, triazamate, trimetacarb, XMC, and xylylcarb, etc.; or organophosphates, e.g., acephate, azamethiphos, azinphosethyl, azinphosmethyl, kazusaphos, chloretoxyphos, chlorfenbinphos, chlormephos, chlorpyrifosmethyl, coumaphos, cyanophos, dimeton-S-methyl, diazinon, dichlorvos / DDVP, dichlor Tophos, dimethoate, dimethylvinphos, disulfon, EPN, ethione, etoprophos, fanflu, phenamiphos, fenitrothion, fenthion, fostiazate, heptenophos, imisiaphos, isofenphos, isopropyl=O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monoclotophos, naled, omethoate, oxydimeton methyl, parathion methyl, fenthoate, phorate, fosalon, fosmet, phosphamidone, foxim, pyrimiphos methyl, profenophos, propetamphos, prothiophos, pyraclophos, pyridaphenthion, quinalphos, sulfotep, tebupyrimphos, temephos, terbuphos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and bamidothion, etc.

[0334] (2) GABA-opening chloride channel blockers, such as cyclic diene organochlorine compounds like chlordane and endosulfan, or phenylpyrazole compounds (fiprole compounds) like ethiprole and fipronil.

[0335] (3) Sodium channel modulators, e.g., pyrethroids, e.g., acrinatrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, biorethmetrin, cycloprothrin, cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, Θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empent Phosphorus [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, cadesrin, monfluorothrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin, pyrethrin (chrysanthemum), resmethrin, silafluofen, tefluthrin, tetramesrin, tetramesrin [(1R)-isomer)], tralomethrin, and transfluthrin, or DDT, or methoxychlor, etc.

[0336] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, e.g., neonicotinoids, e.g., acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradiflon.

[0337] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, e.g., spinosin systems, e.g., spinetram and spinosad.

[0338] (6) Glutamate-opening chloride channel (GluCl) allosteric modulators, such as avermectin / milbemycin derivatives, such as abamectin, emamectin benzoate, lepimectin, and milbemectin.

[0339] (7) Juvenile hormone analogs, such as juvenile hormone derivatives, such as hydroprene, quinoprene, and methoprene, or phenoxycarb, or pyriproxyfen.

[0340] (8) Other nonspecific (multisite) inhibitors, such as alkyl halides, such as methyl bromide and other alkyl halides, or chloropicrin, or sulfuryl fluoride, or borax, or tartaric acid, or methyl isocyanate generators, such as diazomet and metam.

[0341] (9) For example, modulators for stringed organs such as pymetrozine or flonicamide.

[0342] (10) For example, mite growth inhibitors such as clofentezine, hexythiazox, and diflovidazine, or etoxazole.

[0343] (11) Microbial-derived insect midgut endometrium disruptors, e.g., Bacillus thuringiensis ssp. israelensis, Bacillus sphaericus, Bacillus thuringiensis ssp. aizawai, Bacillus thuringiensis ssp. kurstaki, Bacillus thuringiensis ssp. tenebryonis Plant proteins from Bacillus tenebrionis, and Bacillus thuringiensis (Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1), etc.

[0344] (12) Mitochondrial ATP synthase inhibitors, such as ATP disruptors such as diafenthiurone, or organotin compounds, such as azocyclotin, cyhexatine, and fenbutatin oxide, or propargit, or tetradiphon.

[0345] (13) Oxidative phosphorylation uncoupling agents that disrupt the proton gradient, such as chlorfenapyr, DNOC, and sulfuramide.

[0346] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocyclam, and thiosultap sodium salt.

[0347] (15) Chitin biosynthesis inhibitors, type O, such as bistriflurone, chlorfluazurone, diflubenzuron, flucycloxurone, flufenoxurone, hexaflumurone, lufenuron, novaron, nobiflumuron, teflubenzuron, and triflumuron.

[0348] (16) Chitin biosynthesis inhibitors, type 1, e.g., buprofezin.

[0349] (17) Molting disruptors (especially for Diptera, i.e., Diptera), such as cyromazine.

[0350] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

[0351] (19) Octopamine receptor agonists, e.g., amitraz.

[0352] (20) Mitochondrial electron transport chain complex III inhibitors, such as hydramethylnon, acequinosyl, or fluacrypilim.

[0353] (21) Mitochondrial electron transport chain complex I inhibitors, for example, from the group of METI acaricides, e.g., phenazaquine, fenpyroximate, pyrimidifene, pyridaben, tebufenpyrad, and tolfenpyrad, or rotenone (Delice).

[0354] (22) Voltage-gated sodium channel blockers, such as indoxacarb or metaflumizone.

[0355] (23) Acetyl-CoA carboxylase inhibitors, e.g., tetronic acid and tetramic acid derivatives, e.g., spirodiclofen, spiromesifen, spirotetramat.

[0356] (24) Mitochondrial electron transport chain complex IV inhibitors, such as phosphine systems, such as aluminum phosphide, calcium phosphide, phosphine, and zinc phosphide, or cyanides, such as calcium cyanide, potassium cyanide, and sodium cyanide.

[0357] (25) Mitochondrial electron transport chain complex II inhibitors, such as β-ketonitrile derivatives, cyenopyrafen and cyflumetofen, and carboxanilides, such as piflubumi.

[0358] (28) ryanodine receptor modulators, e.g., diamide systems, e.g., 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-Epsilon-Momfluthrin, Flometoquin, Fluazaindolizine, (Fluensulfone) Fluphenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione ione), κ-Bifenthrin, κ-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirodiclofen, Tetramethylfluthrin,Tetraniliprole, tetrachlorantraniliprole, tigolaner, tioxazafen, thiofluoximate, triflumezopyrim, and iodomethane, Bacillus firmus (I-1582, BioNeem) Further formulations based on 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-triazole-5-amine (known from International Publication No. 2006 / 043635) (CAS No. 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)propa-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidine]-1(2H)-yl}(2-chloropyridine-4-yl) )Methanone (known from International Publication No. 2003 / 106457) (CAS No. 637360-23-7), 2-Chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)propa-2-en-1-yl]piperidine-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from International Publication No. 2006 / 003494) (CAS No. 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]deca-3-en-2-one (International Publication No. (Publicly known from Patent Publication No. 2010052161) (CAS No. 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4,5]deca-3-en-4-ylethyl carbonate (Publicly known from Patent Publication No. EP2647626) (CAS No. 1440516-42-6), 4-(buto-2-in-1-yloxy)-6-(3,5-dimethylpiperidine-1-yl)-5-fluoropyrimidine (Publicly known from International Publication No. 2004 / 099160) (CAS No. 792914-58-0), PF1364 (Publicly known from Japanese Patent Publication No. 2010 / 018586) (CAS No. 1204776-60-2),N-[(2E)-1-[(6-chloropyridine-3-yl)methyl]pyridine-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from International Publication No. 2012 / 029672) (CAS No. 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (International Publication No. 2013 / 144 (Known from Publication No. 213) (CAS No. 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (Known from International Publication No. 2010 / 051926) (CAS No. 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(meth Lucarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from Chinese Patent Application Publication No. 103232431) (CAS No. 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)-benzamide, 4-[5- (3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxide-3-thietanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)benzamide (International Publication No. (Publicly known from issue 2013 / 050317(A1)) (CAS number 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide,and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide (International Publication No. 2013 / 162715(A2), International Publication No. (Publicly known from US Patent Application Publication No. 2013 / 162716(A2), US Patent Application Publication No. 2014 / 0213448(A1)) (CAS No. 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 (Publicly 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, Chinese Patent (Publicly known from Patent 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 (International Publication No. 2012 / 034403(A1)) (Publicly known from) (CAS number 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazole-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (Publicly known from International Publication No. 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 No. 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy) Phenyl-hydrazine carboxamide (known from Chinese Patent Application Publication No. 101715774(A)) (CAS number 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazole-2-yl)phenyl-cyclopropanecarboxylic acid ester (known from Chinese Patent Application Publication No. 103524422(A)) (CAS number 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2- [[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-inden[1,2-e][1,3,4]oxadiazine-4a(3H)-methyl carboxylate (known from National 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-triazole-3-yl]phenyl]carbamate]-α-L-mannopyranose (known from U.S. Patent Application Publication No. 2014 / 0275503(A1)) (CAS No. 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazine-3-yl)-3-azabicyclo[3.2.1]octane (CAS No. 1253850-56-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS No. 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (International Publication No. 2007 / 040280(A1), International Publication No. 20070402 (Known from 82(A1)) (CAS number 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazole-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide (Known from International Publication No. 2015 / 058021(A1) and International Publication No. 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 No. 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine (known from International Publication No. 2013 / 115391(A1)) (CAS No. 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]deca-3-e n-2-one (known from International Publication No. 2010 / 066780(A1) and International Publication No. 2011 / 151146(A1)) (CAS No. 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from International Publication No. 2014 / 187846(A1)) (CAS No. 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5] Deca-3-en-4-yl ethyl carboxylate (known from International Publication No. 2010 / 066780(A1) and International Publication No. 2011151146(A1)) (CAS No. 1229023-00-0), N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide (known from German Patent Application Publication No. 3639877(A1) and International Publication No. 2012029672(A1)) (CAS No. 1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide (Known from International Publication No. 2016005276(A1)) (CAS No. 1689566-03-7), [N(Z)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide, (CAS No. 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 International Publication No. 2011 / 105506(A1) and International Publication No. 2016 / 133011(A1)) (CAS No. 1332838-17-1).

[0359] Examples of herbicides that can be mixed with the compound of formula (I) and the composition of the present invention are as follows: Acetochlor, aciflorphen, aciflorphen sodium, acroniphen, alachlor, alidochlor, alloxidim, alloxidim sodium, ametrin, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indole-6-yl)pyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor potassium, aminocyclopyrachlor methyl, aminopyralide, amitorol, ammonium sulfamate, anirophos, aslam, A Trazine, azaphenidine, azimsulfuron, beflubutamide, benazoline, benazoline-ethyl, benfluralin, benfresate, bensulfuron, bensulfuron-methyl, benzlide, bentazon, benzobicyclon, benzofenap, bicyclopyrone, bifenox, viranafos, viranafos-sodium, bispiribac, bispiribac-sodium, bixlozone, bromacil, bromobutide, bromophenoxime, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate, and -octanoate Butachlor, Butaphenacil, Butamiphos, Butenachlor, Buttraline, Butroxidim, Butyrate, Cafenstrol, Carbetamide, Carfentrazone, Carfentrazone-ethyl, Chloramben, Chlorbromulone, 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazole-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidine-2-one, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazole-1-yl)methyl]-4-(methyl {(2,2,2-Trifluoroethoxy)methyl]benzoyl}-1-ethyl-1H-pyrazole-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, chlorophthalim, chlorotolurone, chlortal-dimethyl, 3-[5-chloro-4-(trifluoromethyl)pyridine-2-yl]-4-hydroxy-1-methylimidazolidinion-2-one, chlorsulfuron, synidone, synidone-ethyl, cinmethyline, synosulfuron, crasifos, cretodym, clodinahop, clodinahop- Propargyl, Cromazon, Clomeprop, Clopyralide, Chloransram, Chloransram-methyl, Cumilon, Cyanamide, Cyanazine, Cycloate, Cyclopyranil, Cyclopyrimolate, Cyclosulfamurone, Cycloxidium, Cyhalofop, Cyhalofop-butyl, Cyprazine, 2,4-D, 2,4-D-Butotyl,-Butyl,-Dimethylammonium,-Diolamine,-Ethyl, 2-Ethylhexyl,-Isobutyl,-Isooctyl,-Isopropylammonium,-Potassium -Triisopropanolammonium and -Trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -sodium, Daimuron (daimuron / dymron), Darapon, Dazomet, n-Decanol, Desmedifam, Detosyl-pyrazolate (DTP), Dicanba, Diclobenyl, Dichlorprop, Dichlorprop-P, Diclohop, Diclohop-methyl, Diclohop-P-methyl, Diclothram, Diphenzocort, Diflufenican, Diflufenzopyr, Diflufenzopyr-sodium, Dimeflon, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamide, Dimethenamide-P, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohexa-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 1,3-dimethyl-4-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]-1H-pyrazole-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate, dimethrasulfuron, dinitramine, dinoterb, diphenamide, diquat, diquat-dibromide, dithiopyr, diuron, DMPA, DNOC, endotal, EPTC, esprocarb, ethalfluralin, etamethosulfuron, etamethosulfuron-methyl, ethidine, etofmesate, ethoxyphene, ethoxyphene-ethyl, ethoxysulfuron, etobenzanide, ethyl-[(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(triflu Oromethyl)-3,6-dihydropyrimidine-1(2H)-yl]phenoxy}pyridine-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-benzimidazole-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, phenoxaprop, phenoxaprop-P, phenoxaprop-ethyl, phenoxaprop-P-ethyl, phenoxasulfone, fenquinotrione, phentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, floraslam, fluadifop, fluadifop-P, fluadifop-butyl, fluadifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, fluphenacet, flufenpyr, flufenpyr-ethyl, flumetsuram, flumimicrolac, flumimicrolac-pentyl, flumioxazine, fluomethuron, flurenol, flurenol-butyl, -dimethylammonium, and -methyl, fluorog Lycophene, fluoroglycofen-ethyl, flupropanate, flupyrusulfuron, flupyrusulfuron-methyl-sodium, flulidone, flulochloridone, fluroxypyr, fluroxypyr-meptyl, flulutamone, fluthiaset, fluthiaset-methyl, homesaphen, homesaphen-sodium, horamsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-p-sodium, glufosinate-p-ammonium, glufosinate-p-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium, and -trimethium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl)O-ethyl Isopropylphosphoramidethioate, halaxifen, halaxifen-methyl, halosaphene, halosulfuron, halosulfuron-methyl, haloxyhop, haloxyhop-P, haloxyhop-ethoxyethyl, haloxyhop-P-ethoxyethyl, haloxyhop-methyl, haloxyhop-P-methyl, hexazinone, HW-02, i.e., 1-(dimethoxyphosphoryl)ethyl-(2,4-Dichlorophenoxy)acetate, 4-Hydroxy-1-Methoxy-5-methyl-3-[4-(trifluoromethyl)pyridine-2-yl]imidazolidine-2-one, 4-Hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridine-2-yl]imidazolidine-2-one, (5-Hydroxy-1-methyl-1H-pyrazole-4-yl)(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)methanone, 6-[(2-Hydroxy-6-oxocyclohexa-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione, imazametabenz, imazametabenz-methyl, imazamox, imazamock Su-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazakine, imazakine-ammonium, imazetapir, imazetapir-immonium, imazosulfuron, indanophan, indadiflame, iodosulfuron, iodosulfuron-methyl-sodium, ioxinyl, ioxinyl-octanoate, -potassium, and -sodium, ibuphencarbazone, isoproturone, isouron, isoxaben, isoxaflutol, carbchylate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-Oxazole, Ketospiradox, Lactofen, Renasil, 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, 2-Ethylhexyl and Potassium, Mefenacet, Mefluidide, Mesosulfuron, Mesosulfuron-Methyl, Mesotrione, Metabenzthiazuron, Metam, Metamihop, Metamitron, Metazachlor, Metazosulfuron, Metabenzthiazuron, Methiopyrsulfuron, Methiozoline, 2-({2-[(2-Methoxy Ethoxy)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-pyrazole-5-ylpropane-1-sulfonate, metobromurone, metrachlor, S-metrachlor, methosram, Metoxlon, Metrivudine, Metosulfuron, Metosulfuron-methyl, Molinate, 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-pyrazole-4-yl](2,4-Dichlorophenyl)methanone, Nebulon, Nicosulfuron, Nonanoic acid (pelargonic acid), Norflurazone, Oleic acid (fatty acid), Olbencarb, Orthosulfamuron, Oryzalin, Oxaziargyl, Oxadiazone, Oxasulfuron, Oxadiclomephone, Oxyfluorphene, Paraquat, Paraquat dichloride, Pebrate, Pendimethalin, Penoxuslam, Pentachlorophenol, Pentoxazone, Petoxamide, Petroleum, Fenmedifame Pichloram, picolinafene, pinoxadene, piperofos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxidim, prometon, prometrin, propacrol, propanil, propaxafop, propazine, profam, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propizamide, prosulfocarb, prosulfuron, pyraclonil, pyrafulfen, pilaf, Faveptol-ethyl, pyrasulfolol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenoxime, pyributicarb, pyridafol, pyridate, pyrifthalide, pyriminovac, pyriminovac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxislam, quinchlorac, quinmelac, quinoclamin, quizarophop , quizalopop-ethyl, quizalopop-P, quizalopop-P-ethyl, quizalopop-P-tefuryl, QYM-201, QYR-301, limsulfuron, safluphenacil, cethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfenthrazone, sulfomethane, sulfomethane-methyl, sulfosulfuron, SYN-523, SYP-249, i.e., 1-ethoxy-3-methyl-1-oxobuta-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl SYP-300, i.e., 1-[7-fluoro-3-oxo-4-(propa-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazine-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiurone, tefuryltrione, tenbotrione, tepraloxidim, terbasil, terbucarb, terbumetone, terbutyrazine, terbutrin, tetoflupyrrolimet, tenylchlor, thiazopil, thiencarbazone, thien Carbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenacil, tolpyrate, topramezon, tralcoxidime, triafamone, trialate, triasulfuron, triaziflame, tribenulon, tribenulon-methyl, triclopyr, trietadine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, ZJ-0862, i.e., 3,4-Dichloro-N-{2-[(4,6-dimethoxypyrimidine-2-yl)oxy]benzyl}aniline.

[0360] Examples of plant growth regulators are as follows: Acibenzolar, Acibenzolar-S-methyl, 5-aminolevulinic acid, Ancimidol, 6-benzylaminopurine, Brassinolide, Catechin, Chlormecoat-chloride, Cloprop, Cyclanilide, 3-(cyclopropa-1-enyl)propionic acid, Daminozide, Dazomet, n-Decanol, Dikeglac, Dikeglac-sodium, Endotar, Endotar-dipotassium, -disodium, and -mono(N,N-dimethylalkylammonium), Ethephon, Flumetraline, Flurenol, Flurenol-butyl, Flurprimidol, Forchlorfenuron, Gibberellic acid, Inabenfide, Indole-3-acetic acid (IAA), 4-Indole 3-yl butyrate, isoprothiolane, probenazole, jasmonic acid, maleate hydrazide, mepicote chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, paclobutrazol, N-(2-phenylethyl)-β-alanine, N-phenylphthalamidic acid, prohexadione, prohexadione-calcium, prohydrojasmon, salicylic acid, strigolactone, technazene, tidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

[0361] Examples of drug-induced harm-reducing agents that can be mixed with the compounds of formula (I) and the compositions of the present invention include benoxacol, croquintoset(-methyl), siomethrinyl, cyprosulfamide, dichloramide, fenchlorazole(-ethyl), fenchlorim, flurazole, fluxofenim, flirazole, isoxadifen(-ethyl), mefenpyr(-diethyl), naphthalic anhydride, oxavethrinyl, 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), and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS No. 52836-31-4).

[0362] Examples of nitrification inhibitors that can be mixed with the compound of formula (I) and the composition of the present invention are selected from the group consisting of: 2-(3,4-dimethyl-1H-pyrazole-1-yl)succinic acid, 2-(4,5-dimethyl-1H-pyrazole-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-pyrazole-1-yl)methyl)acetamide, N-((3(5)-methyl-1H-pyrazole-1-yl)methyl)formamide, N-((3(5),4-dimethylpyrazole-1-yl)methyl)formamide, N-((4-chloro-3(5)-methylpyrazole-1-yl)methyl)formamide;Dicyandiamide reaction adducts, ureas and formaldehydes, triazonyl-formaldehyde-dicyandiamide adducts, 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 (nitrapyrine or N-Serve), dicyandiamide, 3,4-dimethylpyrazole phosphate, 4,5-dimethylpyrazole phosphate, 3,4-dimethylpyrazole, 4,5-dimethylpyrazole, ammonium thiosulfate, neem, products based on neem components, linoleic acid, alpha-linoleic acid, methyl p-coumarate, methyl ferulate, methyl 3-(4-hydroxyphenyl)propionate, carandin, brachialactone, p-benzoquinone sorgoleone, 4-amino-1,2,4-triazole hydrochloride, 1-amide-2-thiourea, 2-amino-4-chloro-6-methylpyrimidine, 2-mercapto-benzothiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiodiazole (terazol, etridazole), 2-sulfanilamidothiazole, 3-methylpyrazole, 1,2,4-triazole thiourea, cyanamide, melamine, zeolite powder, catechol, benzoquinone, sodium tetraborate, allylthiourea, chlorate, and zinc sulfate.

[0363] The compound of formula (I) and the compositions of the present invention can be combined with one or more agriculturally beneficial agents.

[0364] Examples of agriculturally beneficial agents include biostimulants, plant growth regulators, plant signaling molecules, growth promoters, microbial stimulant molecules, biomolecules, soil conditioners, nutrients, plant nutrient fortifiers, etc., such as lipochito-oligosaccharides (LCO), chito-oligosaccharides (CO), chitin compounds, flavonoids, jasmonic acid or its derivatives (e.g., jasmonic acid), cytokinins, auxins, gibberellins, abscisic acid, ethylene, brassinosteroids, salicylates, macronutrients and micronutrients, linoleic acid or its derivatives, caliquine, 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, Azospirillum species, (Bacillus) species, Burkholderia species, Candida species, Chryseomonas species, Enterobacter speci...

Claims

1. Equation (I): 【Chemistry 1】 (In the formula, T is oxygen (O) or sulfur (S). n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR ８ And, R ８ is hydrogen, halogen, cyano, or C １ -C ４ -It is alkyl, R １ is hydrogen, hydroxyl, cyano, C １ -C ６ -alkyl, C １ -C ６ -alkoxy, -C(=O)R １０ , -C(=O)(OR １１ ), -S(=O)R １２ , -S(=O) ２ R １２ , -C(=O)N(R １３ ) ２ , or -S(=O) ２ N(R １４ ) ２ and R １０ , R １１ , and R １２ C is independent １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C ３ -C ８ -Cycloalkyl, or C ２ -C ６ - It is Alkenil, R １３ and R １４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C ３ -C ８ -Cycloalkyl, or C ２ -C ６ - It is Alkenil, R ２ and R ３ These are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, and C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Alkoxycarbonyl, or C ３ -C ８ - Is it cycloalkyl? or R ２ and R ３ Together with the carbon atoms to which they are bonded, C ３ -C ８ - Forms a cycloalkyl ring or a 3- to 7-membered heterocyclyl ring, R ４ and R ５ These are independently hydrogen, halogen, cyano, hydroxyl, carboxyl, and C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Alkoxycarbonyl, or C ３ -C ８ - Is it cycloalkyl? or R ４ and R ５ Together with the carbon atoms to which they are bonded, C ３ -C ８ - Forms a cycloalkyl ring or a 3- to 7-membered heterocyclyl ring, or R ２ and R ４ Together with the carbon atoms to which they are bonded, C ３ -C ８ - Forms a cycloalkyl ring or a 3- to 7-membered heterocyclyl ring, and R ３ and R ５ These are independently hydrogen or halogen, or R ２ and R ４ They come together to form a bond, and the formula ＊＊ -C(R ３ ) = C(R ５ ) - ＃＃ (In the ceremony ＊＊ is N(R １ It is a connection point to ), ＃＃ is R ６ Forms the base of (which is a bonding point to), and R ３ and R ５ are independently hydrogen, halogen, or C １ -C ６ -alkyl, and R ６ is C ３ -C １２ -carbocyclyl, C ６ -C １４ -aryl, a 3- to 14-member heterocyclic ring, a 5- to 14-member heteroaryl, C ３ -C １２ -carbocyclyloxy, C ６ -C １４ -aryloxy, a 5- to 14-member heteroaryloxy, a 3- to 14-member heterocyclyloxy, C １ -C ３ -alkoxy, or C １ -C ３ -haloalkoxy, provided that C １ -C ３ - Alkoxy and C １ -C ３ - Haloalkoxys are C ３ -C １２ - Carbocyclyl, C ６ -C １４ - Independently substituted with one substituent selected from the group consisting of aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl, Said C ３ -C １２ - Carbocyclyl, C ６ -C １４ - Aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl are sequentially 1 to 4 R ６Ｓ Substituting as desired with substituents, C ３ -C １２ - Carbocyclyl, C ６ -C １４ -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C ３ -C １２ - Carbocyclyloxy, C ６ -C １４ - Aryloxys, 5- to 14-membered heteroaryloxys, and 3- to 14-membered heterocyclyloxys have 1 to 4 R ６Ｓ Substituting as desired with substituents, R ６Ｓ These are independently halogen, cyano, isocyano, nitro, hydroxyl, oxo, mercapto, pentafluorosulfanil, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C ３ -C ８ -Cycloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C ３ -C ８ -Cycloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ -Cycloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ８ -Cycloalkenyl, C ６ -C １４ -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -N(R) １５ ) ２ , -C(=O)R １６ , -C(=O)(OR １７ ), -C(=O)N(R １８ ) ２ , -S (=O) ２ N(R) １９ ) ２ , -O-Si(C １ -C ６ -Alkyl) ３ , or -Si(C １ -C ６ -Alkyl) ３ And, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ -Haloalkylsulfonyl, -O-Si(C １ -C ６ -Alkyl) ３ , and -Si(C １ -C ６ -Alkyl) ３ is cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl and 3- to 7-membered heterocyclyl groups, and Said C ３ -C ８ -Cycloalkylsulfanyl, C ３ -C ８ -Cycloalkylsulfinyl, C ３ -C ８ -Cycloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ８ -Cycloalkenyl, C ６ -C １４ -aryl, 5- or 6-membered heteroaryl, and 3- to 7-membered heterocyclyls are halogens, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 4 substituents independently selected from the group consisting of halocycloalkyl groups, or Two carbon atoms bonded to the same carbon atom １ -C ６ - Alkyl substituents are C ３ -C ８ - Forms a cycloalkyl ring, or Two R ６Ｓ Substituents can optionally be added together with the carbon atom to which they are bonded (C) ３ -C ８ - Forms a cycloalkyl ring, and R １５ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, or C ３ -C ８ - Cycloalkyl, Said C １ -C ６ - Alkyl is cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl and 3- to 7-membered heterocyclyl groups, and Said C ３ -C ８ -Cycloalkyl includes halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 4 substituents independently selected from the group consisting of halocycloalkyl groups, R １６ , R １７ , R １８ , and R １９ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, or C １ -C ６ - It is a haloalkyl, Said C １ -C ６ - Alkyl or C １ -C ６ - Haloalkyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl and 3- to 7-membered heterocyclyl groups, Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. p is 0, 1, 2, 3, or 4. R ７ These are halogens, cyano, nitro, hydroxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Cycloalkenyl, -N(R) ２０ ) ２ , -C(=O)R ２１ , -C(=O)(OR ２２ ), -C(=O)N(R ２３ ) ２ or -S (=O) ２ N(R) ２４ ) ２ And, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, and C １ -C ６ - Haloalkylsulfonyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, C ３ -C ８ - Cycloalkyl and C ３ -C ８ -Cycloalkenyls are halogens, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, and R ２０ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, or C ３ -C ８ - Cycloalkyl, C １ -C ６ - Alkyl is cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups. and C ３ -C ８ -Cycloalkyl includes halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, R ２１ , R ２２ , R ２３ , and R ２４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl or C １ -C ６ - It is a haloalkyl, C １ -C ６ - Alkyl and C １ -C ６ - Haloalkyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, or Two substituents R ７ They become C together with the carbon atoms to which they are bonded. ３ -C ８ - Forms a cycloalkyl ring, Q is C ６ -C １４ - Aryl, C ３ -C １２ - Carbocyclyl, 3- to 14-membered heterocyclyl, or 5- to 14-membered heteroaryl, C ６ -C １４ - Aryl, C ３ -C １２ -Carbocyclyls, 3- to 14-membered heterocyclyls, and 5- to 14-membered heteroaryls are halogens, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkylcarbonyl, C １ -C ６ - Haloalkylcarbonyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ -Alkoxy-C １ -C ６ - Alkyl, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ６ -Cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , -OC(=O)R ２５ , -NR ２６ C(=O)R ２７ , -C(=O)N(R ２８ ) ２ , C(=S)R ２９ , -C(=S)N(R ３０ ) ２ , -C(=NR ３１ ) R ３２ , -C(=NOR ３３ ) R ３４ , and -N(R ３５ ) ２ One to five Qs are independently selected from the group consisting of the following: Ｓ Substituting as desired with substituents, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkylcarbonyl, C １ -C ６ - Haloalkylcarbonyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ -Alkoxy-C １ -C ６ - Alkyl, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ -Haloalkylsulfonyl, -O-Si(C １ -C ６ -Alkyl) ３ , and -Si(C １ -C ６ -Alkyl) ３ C is cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ６ -Cycloalkenyls, 3- to 7-membered heterocyclyls, and 5- to 14-membered heteroaryls are halogens, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyl, C ２ -C ６ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyls and 3- to 7-membered heterocyclyls, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyls and 3- to 7-membered heterocyclines are sequentially linked to the carbon atoms to which they are bonded, C ３ -C ８ -Optionally substituted with two substituents that form a cycloalkyl group, R ２５ , R ２６ , R ２７ , R ２８ , R ２９ , R ３０ , R ３１ , R ３２ , R ３３ , and R ３４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, or C １ -C ６ - It is an alkoxy, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, and C １ -C ６ - Alkoxy are cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, and R ３５ These are independently hydrogen, hydroxyl, and C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenil, or C ３ -C ８ - Cycloalkyl, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C ２ -C ６ - Alkenyl, and C ２ -C ６ - Haloalkenyls are cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, Said C ３ -C ８ -Cycloalkyl includes halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyl, C ２ -C ６ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyls and 3- to 7-membered heterocyclyls, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyls and 3- to 7-membered heterocyclines are sequentially linked to the carbon atoms to which they are bonded, C ３ -C ８ - Compounds (optionally substituted with two substituents forming a cycloalkyl group), Alternatively, their N-oxides, salts, or solvates, or solvates of the salts or N-oxides thereof.

2. T is oxygen (O) or sulfur (S). n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR ８ And, R ８ is hydrogen, fluoro, chloro, methyl, or ethyl, R １ is hydrogen, hydroxyl, C １ -C ４ - Alkyl, C １ -C ４ -alkoxy, or -C(=O)R １０ And, R １０ C １ -C ４ -It is alkyl, R ２ and R ３ These are independently hydrogen, fluoro, chloro, or C １ -C ４ -It is alkyl, R ４ and R ５ These are independently hydrogen, halogen, and C １ -C ４ - Alkyl, or C ３ -C ６ - Is it cycloalkyl? or R ４ and R ５ Together with the carbon atoms to which they are bonded, C ３ -C ６ - Forms a cycloalkyl ring, or R ２ and R ４ The formula ＊＊ -C(R ３ ) = C(R ５ ) - ＃＃ (In the ceremony ＊＊ is N(R １ It is a connection point to ), ＃＃ is R ６ Forms the base of (which is a bonding point to), and R ３ and R ５ These are independently hydrogen, fluoro, or C １ -C ４ -It is alkyl, R ６ C ５ -C １０ -Carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, 5- to 10-membered heteroaryl, C ５ -C １０ - Carbocyclyloxy, phenoxy, benzyloxy, 5-membered to 10-membered heteroaryloxy, 5-membered to 10-membered heterocyclyloxy, C １ -C ３ - Alkoxy, or C １ -C ３ - It is a haloalkoxy, C １ -C ３ - Alkoxy and C １ -C ３ - Haloalkoxys are C ５ -C １０ - Independently substituted with one substituent selected from the group consisting of carbocyrill, phenyl, naphthyl, 5- to 10-membered heterocyclyl, and 5- to 10-membered heteroaryl, Said C ５ -C １０ -Carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, and 5- to 10-membered heteroaryl are sequentially 1 to 3 R ６Ｓ Substituting as desired with substituents, C ５ -C １０ -Carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, 5- to 10-membered heteroaryl, C ５ -C １０ -Carbocyclyloxy, phenoxy, naphthyloxy, 5- to 10-membered heteroaryloxy, and 5- to 10-membered heterocyclyloxy contain 1 to 3 R ６Ｓ Substituting as desired with substituents, R ６Ｓ These are independently halogen, cyano, oxo, and C １ -C ４ - Alkyl, C １ -C ４ - Haloalkyl, C １ -C ４ - Alkoxy, C １ -C ４ - Haloalkoxy, C ２ -C ４ - Alkenil, C ２ -C ４ - Haloalkenyl, C ２ -C ４ - Alkinyl, C ２ -C ４ - Haloalkynyl, C ３ -C ６ - Cycloalkyl, C ３ -C ６ -Cycloalkenyl, phenyl, naphthyl, thienyl, pyrazolyl, imidazolyl, pyridinyl, pyrimidinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, -C(=O)R １６ , or -C (=O) (OR １７ ) and said 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 -haloalkenyl, C ２ -C ４ -alkynyl, and C ２ -C ４ -haloalkynyl is further optionally substituted with one or two substituents independently selected from the group consisting of cyano, hydroxyl, C １ -C ４ -alkoxy, C １ -C ４ -haloalkoxy, -O-Si(C １ -C ４ -alkyl) ３ -Si(C １ -C ４ -alkyl) ３ and C ３ -C ６ -cycloalkyl and is further optionally substituted, and Said C ３ -C ６ - Cycloalkyl, C ３ -C ６ -Cycloalkenyl, phenyl, naphthyl, thienyl, pyrazolyl, imidazolyl, pyridinyl, pyrimidinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, and tetrahydropyranyl are halogens, C １ -C ４ - Alkyl, C １ -C ４ - Haloalkyl, and C １ -C ６ - Further optionally substituted with one or two substituents independently selected from the group consisting of alkoxycarbonyls, R １６ and R １７ C is independent １ -C ４ -It is alkyl, The aforementioned ring Y, together with either a pyridine ring or a pyridazine ring, is represented by formulas (II-a) to (II-aa): 【Chemistry 2-1】 【Chemistry 2-2】 (In the formula, ＊ This is a bonding site to the -O-Q group, ＃ is -N(R １ It is a connection point to ), G stands for oxygen (O), sulfur (S), or NR ７Ｌ And, R ７Ｌ is hydrogen, C １ -C ４ - Alkyl, C １ -C ４ - Haloalkyl, or C ３ -C ８ - It is a cycloalkyl, p is 0, 1, 2, 3, or 4. x １ is either 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 Hydrogen is independent of hydrogen, Hydroxyl, halogen, C １ -C ４ - Alkyl, C １ -C ４ - Haloalkyl, C １ -C ４ - Alkoxy, C １ -C ４ - Haloalkoxy, or C ３ -C ８ - It is a cycloalkyl, R ７Ｈ is hydrogen, C １ -C ４ - Alkyl, or C １ -C ４ - It is a haloalkyl, R ７Ｋ methylidene, halomethylidene, halogen, hydroxyl, oxo, C １ -C ４ - Alkyl, C １ -C ６ - Haloalkyl, or C ３ -C ６ - Is it cycloalkyl? or Two substituents R ７Ｋ together with the carbon atom to which they are attached form a group of C ３ -C ８ - cycloalkyl ring) Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indlinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxynyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro- 5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, phlopyridinyl, thienothiophenyl, or thienothiazolyl, which contains phenyl, naphthyl, Bicyclo[4.2.0]octa-1(6)2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, indlinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxynyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, dihydro-5H-cyclopenta[b]pyridinyl Lysinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridadinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, phlopyridinyl, thienothiophenyl, and thienothiazolyl are halogens, cyano, nitro, hydroxyl, formyl, C １ -C ４ - Alkyl, C １ -C ４ - Haloalkyl, C １ -C ４ - Alkylcarbonyl, C １ -C ４ - Haloalkylcarbonyl, C １ -C ４ - Alkoxy, C １ -C ４ - Haloalkoxy, C １ -C ４ -Alkoxy-C １ -C ４ - Alkyl, C ２ -C ４ - Alkenil, C ２ -C ４ - Haloalkenyl, C ２ -C ４ - Alkinyl, C ２ -C ４ - Haloalkynyl, C １ -C ４ -Alkyl sulfanyl, C １ -C ４ - Haloalkylsulfanyl, C ３ -C ６ -Cycloalkyl, oxetanyl, and -N(R) ３５ ) ２ One to three Qs are independently selected from the group consisting of the following: Ｓ Substituting as desired with substituents, Said C ３ -C ６ -Cycloalkyls are halogens, C １ -C ４ - Alkyl, and C １ -C ４ -Optionally substituted with one or two substituents independently selected from the group consisting of haloalkyl groups, and R ３５ These are independently hydrogen or C １ -C ４ - A compound of formula (I) according to claim 1, which is alkyl, Alternatively, their N-oxides, salts, or solvates, or solvates of the salts or N-oxides thereof.

3. T is oxygen (O) or sulfur (S). n is 0 or 1. m is 0 or 1. A is nitrogen (N) or CR ８ And, R ８ is hydrogen or methyl, R １ is hydrogen, hydroxyl, C １ -C ４ - Alkyl, C １ -C ４ -alkoxy, or -C(=O)R １０ And, R １０ is methyl or ethyl, R ２ and R ３ It is hydrogen, R ４ and R ５ These are independently hydrogen, fluoro, methyl, or ethyl, or R ２ and R ４ The formula ＊＊ -C(R ３ ) = C(R ５ ) - ＃＃ (In the ceremony ＊＊ is N(R １ It is a connection point to ), ＃＃ is R ６ Forms the base of (which is a bonding point to), and R ３ and R ５ It is hydrogen, R ６ This includes tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanil, isochromanil, thiochromanil, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, furanil, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, indolyl, benzothiazolyl, phenoxy, or benzyloxy, Tetrahydronaphthalenyl, spiro[cyclopropane-1,2'-indan]yl, phenyl, dihydrobenzofuranyl, chromanil, isochromanil, thiochromanil, 1,3-benzodioxolyl, dihydro-1,4-benzodioxynyl, tetrahydrobenzothienyl, furanil, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, indolyl, benzothiazolyl, phenoxy, and benzyloxy contain 1 to 3 R ６Ｓ Substituting as desired with substituents, R ６Ｓ These are halogen, cyano, oxo, and C １ -C ４ - Alkyl, difluoromethyl, trifluoromethyl, C １ -C ４ - Alkoxy, difluoromethoxy, trifluoromethoxy, C ２ -C ４ - Alkenil, C ２ -C ４ - Alkinyl, C ３ -C ６ - Cycloalkyl, C ５ -C ６ -Cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, or -C(=O)R １６ And, R １６ C １ -C ４ -It is alkyl, The ring Y, together with either a pyridine ring or a pyridazine ring, is one of the following: formula (II-a), formula (II-b), formula (II-g), formula (II-h), formula (II-i), formula (II-r), formula (II-s), formula (II-u), or formula (II-v): 【Transformation 3】 (In the formula, ＊ This is a bonding site to the -O-Q group, ＃ is -N(R １ It is a connection point to ), p is 0, 1, or 2. x １ is either 1 or 2, x ２ is 0, 1, or 2, G stands for oxygen (O), or NR ７Ｌ And, R ７Ｌ It is hydrogen, R ７Ａ It is hydrogen, R ７Ｂ is hydrogen, fluoro, methyl, or methoxy, R ７Ｃ is hydrogen, fluoro, methyl, or methoxy, R ７Ｄ It is hydrogen, R ７Ｅ It is hydrogen, R ７Ｆ is hydrogen, and R ７Ｋ (The group is hydroxyl or methyl) Q is phenyl, pyridinyl, or pyrimidinyl, Phenyl, pyridinyl, and pyrimidinyl are halogens, cyano, and C １ -C ４ - Alkyl, difluoromethyl, trifluoromethyl, C １ -C ４ - Alkoxy, difluoromethoxy, trifluoromethoxy, C ２ -C ４ - One or two Q independently selected from the group consisting of alkenyl, cyclopropyl, and cyclobutyl Ｓ A compound of formula (I) according to claim 1 or 2, which may be optionally substituted with a substituent. Alternatively, their N-oxides, salts, or solvates, or solvates of the salts or N-oxides thereof.

4. n is 0 or 1. m is 0 or 1. R ２ and R ３ It is hydrogen, R ４ and R ５ These are independently hydrogen, fluoro, methyl, or ethyl, or R ４ and R ５ These, together with the carbon atoms to which they are bonded, form a cyclopropyl ring. or R ２ and R ４ The formula ＊＊ -C(R ３ ) = C(R ５ ) - ＃＃ (In the ceremony ＊＊ is N(R １ It is a connection point to ), and ＃＃ is R ６ Forms the base of (which is a bonding point to) A compound of formula (I) according to any one of claims 1 to 3.

5. n is 0, m is 0, and R ６ These include naphthyl, indanyl, tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, dihydrobenzofuranyl, dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro- 1,4-Benzodioxinyl, tetrahydrobenzothiophenyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranil, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, dihydro-4H-cyclopenta[b]thiophenyl, dihydro-4H-cyclopenta[d] Thiazolyl, tetrahydropyrazolo[1,5-a]pyridinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophene These are nyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, flo[2,3-d]isoxazolyl, or thieno[2,3-d]isothiazolyl. Naphthyl, indanyl, tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, spiro[cyclopropane-2,1'-indan]-1-yl, spiro[cyclopropane-1,2'-tetralin]-1-yl, dihydrobenzofuranyl, dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, isothiochromanyl, dihydro-1,4- Benzodioxynyl, tetrahydrobenzothiophenyl, dihydro-5H-cyclopenta[b]pyridinyl, tetrahydrobenzofuranil, tetrahydrobenzoxazolyl, tetrahydrobenzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydroindazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, dihydro-4H-cyclopenta[b]thiophenyl, dihydro-4H-cyclopenta[d]thiazolyl, Tetrahydropyrazolo[1,5-a]pyridinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, tetrahydroimidazo[1,2-a]pyridinyl, dihydro-5H-thieno[3,2-b]pyranyl, spiro[chroman-3,1'-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1'-cyclopropane]-yl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothia Zolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[3,2-c]pyridinyl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, thieno[3,2-b]pyrrolyl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, flu[2,3-d]isoxazolyl, and thieno[2,3-d]isothiazolyl have one or two substituents R ６Ｓ Replaced as desired by R ６Ｓ These are halogen, cyano, oxo, and C １ -C ４ - Alkyl, C １ -C ４ - Haloalkyl, C １ -C ４ - Alkoxy, C １ -C ４ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Alkinyl, C ３ -C ６ -Cycloalkyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, -C(=O)R １６ , and -C (=O) (OR １７ Independently selected from the group consisting of, Said C ３ -C ６ -Cycloalkyl, phenyl, pyrazolyl, imidazolyl, and pyridinyl are fluoro, chloro, C １ -C ４ - Alkyl, and C １ -C ４ -Optionally further substituted with one or two substituents independently selected from the group consisting of haloalkyl groups, and R １６ C １ -C ４ -It is alkyl, R １７ is hydrogen or C １ -C ４ - A compound of formula (I) according to any one of claims 1 to 4, wherein the compound is alkyl.

6. n is 0 or 1. m is 1, and R ６ is phenyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, phenyloxy, or benzyloxy, Phenyl, furanyl, pyrazolyl, thienyl, pyridinyl, pyrimidinyl, phenyloxy, or benzyloxy may have one or two substituents R ６Ｓ Replaced as desired, R ６Ｓ These are independently halogen, cyano, and C １ -C ４ - Alkyl, difluoromethyl, trifluoromethyl, C １ -C ４ - Alkoxy, difluoromethoxy, trifluoromethoxy, C ２ -C ４ - Alkenil, C ２ -C ４ - Alkinyl, C ３ -C ６ - Cycloalkyl, C ３ -C ６ -Cycloalkenyl, phenyl, pyrazolyl, imidazolyl, pyridinyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, or -C(=O)R １６ And, R １６ C １ -C ４ - It is alkyl, A compound of formula (I) according to any one of claims 1 to 4.

7. Q is phenyl or pyridinyl, Phenyl or pyridinyl is a halogen, cyano, C １ -C ４ - Alkyl, difluoromethyl, trifluoromethyl, C １ -C ４ - One or two Q independently selected from the group consisting of alkoxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, or cyclobutyl Ｓ A compound of formula (I) according to any one of claims 1 to 6, which may be optionally substituted with substituents.

8. A composition for controlling plant pathogenic fungi, comprising at least one compound of formula (I) as described in any one of claims 1 to 7, and at least one carrier and / or surfactant.

9. A method for controlling harmful microorganisms in crop protection and industrial material protection, characterized by applying at least one compound of formula (I) described in any one of claims 1 to 7 and / or the composition described in claim 8 to the harmful microorganisms and / or their habitat.

10. Use of one or more compounds of formula (I) according to any one of claims 1 to 7 and / or the composition according to claim 8 for controlling harmful microorganisms in crop protection and protection of industrial materials.

11. Equation (I-a): 【Chemistry 4】 (In the formula, m, n, p, A, Q, Y, R ２ , R ３ , R ４ , R ５ , R ６ , and R ７ is the same as the definition of any one of claims 1 to 7, and T is oxygen (O), R １ is hydrogen, hydroxyl, cyano, or C １ -C ６ A process for preparing a compound (which is alkyl), The aforementioned compound is given by formula (1): 【Transformation 5】 (wherein p, A, Q, T, Y, and R) ７ This is the same as the definition above, and U １ is hydroxyl, halogen, or C １ -C ６ - Compounds that are alkoxy Formula (2): 【Transformation 6】 (In the formula, m, n, R １ , R ２ , R ３ , R ４ , R ５ , and R ６ A process prepared by reacting an amine or salt thereof (which is the same as the definition above). 【Request Item 12】 【Chemistry 7】 (In the formula, m, n, p, A, Q, Y, R ２ , R ３ , R ４ , R ５ , R ６ , and R ７ is the same as the definition of any one of claims 1 to 7, and T is oxygen (O), R １ is hydrogen, C １ -C ６ - Alkyl, or C １ -C ６ A process for preparing compounds (which are alkoxy), The aforementioned compound is given by formula (3): 【Transformation 8】 (In the formula, m, n, p, A, T, Y, R 1 , R ２ , R ３ , R ４ , R ５ , R ６ , and R ７ This is the same as the definition above, and X １ Compounds of halogens, Formula (4): 【Chemistry 9】 The compound (where Q is the same as defined above) and A process prepared by reacting in the presence of a base and, optionally, a transition metal catalyst such as a copper salt or complex.

13. A process for preparing the compound of formula (I-a-1) according to claim 12, wherein the reaction between the compound of formula (3) and the compound of formula (4) is carried out in the presence of an additional ligand.

14. Formula (1): 【Chemistry 10】 (In the ceremony A is nitrogen (N) or CR ８ And, R ８ is hydrogen, halogen, cyano, or C １ -C ４ -It is alkyl, U １ is hydroxyl, halogen, or C １ -C ６ - It is an alkoxy, Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. The resulting bicyclic heteroaryl is not quinoline, p is 0, 1, 2, 3, or 4. R ７ These are halogens, cyano, nitro, hydroxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Cycloalkenyl, -N(R) ２０ ) ２ , -C(=O)R ２１ , -C(=O)(OR ２２ ), -C(=O)N(R ２３ ) ２ , or -S (=O) ２ N(R) ２４ ) ２ And, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, C ３ -C ８ - Cycloalkyl and C ３ -C ８ -Cycloalkenyls are halogens, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, and R ２０ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, or C ３ -C ８ - Cycloalkyl, C １ -C ６ - Alkyl is cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups. and C ３ -C ８ -Cycloalkyl includes halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, R ２１ , R ２２ , R ２３ , and R ２４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl or C １ -C ６ - It is a haloalkyl, C １ -C ６ - Alkyl and C １ -C ６ - Haloalkyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, or Two substituents R ７ They become C together with the carbon atoms to which they are bonded. ３ -C ８ - Forms a cycloalkyl ring, Q is C ６ -C １４ - Aryl, C ３ -C １２ - Carbocyclyl, 3- to 14-membered heterocyclyl, or 5- to 14-membered heteroaryl, C ６ -C １４ - Aryl, C ３ -C １２ -Carbocyclyls, 3- to 14-membered heterocyclyls, and 5- to 14-membered heteroaryls are halogens, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkylcarbonyl, C １ -C ６ - Haloalkylcarbonyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ -Alkoxy-C １ -C ６ - Alkyl, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ６ -Cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , -OC(=O)R ２５ , -NR ２６ C(=O)R ２７ , -C(=O)N(R ２８ ) ２ , C(=S)R ２９ , -C(=S)N(R ３０ ) ２ , -C(=NR ３１ ) R ３２ , -C(=NOR ３３ ) R ３４ , and -N(R ３５ ) ２ One to five Qs are independently selected from the group consisting of the following: Ｓ Substituting as desired with substituents, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkylcarbonyl, C １ -C ６ - Haloalkylcarbonyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ -Alkoxy-C １ -C ６ - Alkyl, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ -Haloalkylsulfonyl, -O-Si(C １ -C ６ -Alkyl) ３ , and -Si(C １ -C ６ -Alkyl) ３ C is cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ６ -Cycloalkenyls, 3- to 7-membered heterocyclyls, and 5- to 14-membered heteroaryls are halogens, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyl, C ２ -C ６ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyls and 3- to 7-membered heterocyclyls, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyls and 3- to 7-membered heterocyclines are sequentially linked to the carbon atoms to which they are bonded, C ３ -C ８ -Optionally substituted with two substituents that form a cycloalkyl group, R ２５ , R ２６ , R ２７ , R ２８ , R ２９ , R ３０ , R ３１ , R ３２ , R ３３ , and R ３４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, or C １ -C ６ - It is an alkoxy, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, and C １ -C ６ - Alkoxy are cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, and R ３５ These are independently hydrogen, hydroxyl, and C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenil, or C ３ -C ８ - Cycloalkyl, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C ２ -C ６ - Alkenyl, and C ２ -C ６ - Haloalkenyls are cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, Said C ３ -C ８ -Cycloalkyl includes halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyl, C ２ -C ６ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyls and 3- to 7-membered heterocyclyls, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyls and 3- to 7-membered heterocyclines are sequentially linked to the carbon atoms to which they are bonded, C ３ -C ８ - Compounds (optionally substituted with two substituents forming a cycloalkyl group), Alternatively, their N-oxides, salts, or solvates, or solvates of the salts or N-oxides thereof.

15. Formula (1): 【Chemistry 11】 (In the ceremony A is N or CR ８ And, R ８ is hydrogen, halogen, or C １ -C ４ -It is alkyl, U １ is hydroxyl, halogen, or C １ -C ６ - It is an alkoxy, Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. The resulting bicyclic heteroaryl is not quinoline, p is 0, 1, 2, 3, or 4. R ７ These are halogens, cyano, nitro, hydroxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Cycloalkenyl, -N(R) ２０ ) ２ , -C(=O)R ２１ , -C(=O)(OR ２２ ), -C(=O)N(R ２３ ) ２ or -S (=O) ２ N(R) ２４ ) ２ And, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, C ３ -C ８ - Cycloalkyl and C ３ -C ８ -Cycloalkenyls are halogens, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, and R ２０ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, or C ３ -C ８ - Cycloalkyl, C １ -C ６ - Alkyl is cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups. and C ３ -C ８ -Cycloalkyl includes halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, R ２１ , R ２２ , R ２３ , and R ２４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl or C １ -C ６ - It is a haloalkyl, C １ -C ６ - Alkyl and C １ -C ６ - Haloalkyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, or Two substituents R ７ They become C together with the carbon atoms to which they are bonded. ３ -C ８ - Forms a cycloalkyl ring, Q is C ６ -C １４ - Aryl, C ３ -C １２ - Carbocyclyl, 3- to 14-membered heterocyclyl, or 5- to 14-membered heteroaryl, C ６ -C １４ - Aryl, C ３ -C １２ -Carbocyclyls, 3- to 14-membered heterocyclyls, and 5- to 14-membered heteroaryls are halogens, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkylcarbonyl, C １ -C ６ - Haloalkylcarbonyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ -Alkoxy-C １ -C ６ - Alkyl, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ６ -Cycloalkenyl, 3- to 7-membered heterocyclyl, 5- to 14-membered heteroaryl, -O-Si(C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , -OC(=O)R ２５ , -NR ２６ C(=O)R ２７ , -C(=O)N(R ２８ ) ２ , C(=S)R ２９ , -C(=S)N(R ３０ ) ２ , -C(=NR ３１ ) R ３２ , -C(=NOR ３３ ) R ３４ , and -N(R ３５ ) ２ One to five Qs are independently selected from the group consisting of the following: Ｓ Substituting as desired with substituents, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkylcarbonyl, C １ -C ６ - Haloalkylcarbonyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ -Alkoxy-C １ -C ６ - Alkyl, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ -Haloalkylsulfonyl, -O-Si(C １ -C ６ -Alkyl) ３ , and -Si(C １ -C ６ -Alkyl) ３ C is cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ６ -Cycloalkenyls, 3- to 7-membered heterocyclyls, and 5- to 14-membered heteroaryls are halogens, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyl, C ２ -C ６ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyls and 3- to 7-membered heterocyclyls, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyls and 3- to 7-membered heterocyclines are sequentially linked to the carbon atoms to which they are bonded, C ３ -C ８ -Optionally substituted with two substituents that form a cycloalkyl group, R ２５ , R ２６ , R ２７ , R ２８ , R ２９ , R ３０ , R ３１ , R ３２ , R ３３ , and R ３４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, or C １ -C ６ - It is an alkoxy, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, and C １ -C ６ - Alkoxy are cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, and R ３５ is hydrogen, hydroxyl, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenil, or C ３ -C ８ - Cycloalkyl, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C ２ -C ６ - Alkenyl, and C ２ -C ６ - Haloalkenyls are cyano, amino, nitro, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Halocycloalkyl, -Si(C １ -C ６ -Alkyl) ３ , and optionally substituted with 1 to 3 substituents independently selected from the group consisting of 3-membered to 7-membered heterocyclines, Said C ３ -C ８ -Cycloalkyl includes halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyl, C ２ -C ６ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of alkenyls and 3- to 7-membered heterocyclyls, Said C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Halocycloalkyls and 3- to 7-membered heterocyclines are sequentially linked to the carbon atoms to which they are bonded, C ３ -C ８ (Optionally substituted with two substituents that form a cycloalkyl group.) The compound, Alternatively, their N-oxides, salts, or solvates, or solvates of the salts or N-oxides thereof.

16. Formula (3): 【Chemistry 12】 (In the ceremony X １ is halogen, n is 1, m is 1, A is nitrogen (N) or CR ８ And, R ８ is hydrogen, halogen, cyano, or C １ -C ４ -It is alkyl, R １ is hydrogen, hydroxyl, cyano, C １ -C ６ - Alkyl, C １ -C ６ -alkoxy, -C(=O)R １０ , -C(=O)(OR １１ ), -S(=O)R １２ , -S (=O) ２ R １２ , -C(=O)N(R １３ ) ２ , or -S (=O) ２ N(R) １４ ) ２ And, R １０ , R １１ , and R １２ C is independent １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C ３ -C ８ -Cycloalkyl, or C ２ -C ６ - It is Alkenil, R １３ and R １４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C ３ -C ８ -Cycloalkyl, or C ２ -C ６ - It is Alkenil, R ２ and R ３ It is independently hydrogen, R ４ and R ５ These are independently hydrogen or fluoro, R ６ C ３ -C １２ - Carbocyclyl, C ６ -C １４ -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C ３ -C １２ - Carbocyclyloxy, C ６ -C １４ - Aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C １ -C ３ - Alkoxy, or C １ -C ３ - It is a haloalkoxy, C １ -C ３ - Alkoxy and C １ -C ３ - Haloalkoxys are C ３ -C １２ - Carbocyclyl, C ６ -C １４ - Independently substituted with one substituent selected from the group consisting of aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl, Said C ３ -C １２ - Carbocyclyl, C ６ -C １４ - Aryl, 3- to 14-membered heterocyclyl, and 5- to 14-membered heteroaryl are sequentially 1 to 4 R ６Ｓ Substituting as desired with substituents, C ３ -C １２ - Carbocyclyl, C ６ -C １４ -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C ３ -C １２ - Carbocyclyloxy, C ６ -C １４ - Aryloxys, 5- to 14-membered heteroaryloxys, and 3- to 14-membered heterocyclyloxys have 1 to 4 R ６Ｓ Substituting as desired with substituents, R ６Ｓ These are independently halogen, cyano, isocyano, nitro, hydroxyl, oxo, mercapto, pentafluorosulfanil, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C ３ -C ８ -Cycloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C ３ -C ８ -Cycloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ -Cycloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ８ -Cycloalkenyl, C ６ -C １４ -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, -N(R) １５ ) ２ , -C(=O)R １６ , -C(=O)(OR １７ ), -C(=O)N(R １８ ) ２ , -S (=O) ２ N(R) １９ ) ２ , -O-Si(C １ -C ６ -Alkyl) ３ , or -Si(C １ -C ６ -Alkyl) ３ And, Said C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C ２ -C ６ - Alkenyloxy, C ２ -C ６ - Haloalkenyloxy, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ -Haloalkylsulfonyl, -O-Si(C １ -C ６ -Alkyl) ３ , and -Si(C １ -C ６ -Alkyl) ３ is cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl and 3- to 7-membered heterocyclyl groups, and Said C ３ -C ８ -Cycloalkylsulfanyl, C ３ -C ８ -Cycloalkylsulfinyl, C ３ -C ８ -Cycloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Cycloalkoxy, C ３ -C ８ -Cycloalkenyl, C ６ -C １４ -aryl, 5- or 6-membered heteroaryl, and 3- to 7-membered heterocyclyls are halogens, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 4 substituents independently selected from the group consisting of halocycloalkyl groups, or Two carbon atoms bonded to the same carbon atom １ -C ６ - Alkyl substituents are C ３ -C ８ - Forms a cycloalkyl ring, or Two R ６Ｓ Substituents can optionally be added together with the carbon atom to which they are bonded to C ３ -C ８ - Forms a cycloalkyl ring, and R １５ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, or C ３ -C ８ - Cycloalkyl, Said C １ -C ６ - Alkyl is cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl and 3- to 7-membered heterocyclyl groups, and Said C ３ -C ８ -Cycloalkyl includes halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 4 substituents independently selected from the group consisting of halocycloalkyl groups, R １６ , R １７ , R １８ , and R １９ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, or C １ -C ６ - It is a haloalkyl, Said C １ -C ６ - Alkyl or C １ -C ６ - Haloalkyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ - Cycloalkyl, C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl and 3- to 7-membered heterocyclyl groups, Ring Y forms a bicyclic heterocyclil or bicyclic heteroaryl with either a pyridine ring or a pyridazine ring, respectively. p is 0, 1, 2, 3, or 4. R ７ These are halogens, cyano, nitro, hydroxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyl, C ３ -C ８ - Cycloalkyl, C ３ -C ８ -Cycloalkenyl, -N(R) ２０ ) ２ , -C(=O)R ２１ , -C(=O)(OR ２２ ), -C(=O)N(R ２３ ) ２ , or -S (=O) ２ N(R) ２４ ) ２ And, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C ２ -C ６ - Alkenil, C ２ -C ６ - Haloalkenyl, C ２ -C ６ - Alkinyl, C ２ -C ６ - Haloalkynyl, C １ -C ６ -Alkyl sulfanyl, C １ -C ６ - Haloalkylsulfanyl, C １ -C ６ -Alkyl sulfinyl, C １ -C ６ - Haloalkylsulfinyl, C １ -C ６ - Alkyl sulfonyl, C １ -C ６ - Haloalkylsulfonyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, C ３ -C ８ - Cycloalkyl and C ３ -C ８ -Cycloalkenyls are halogens, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, and R ２０ Hydrogen and C are independent of each other. １ -C ６ - Alkyl, or C ３ -C ８ - Cycloalkyl, C １ -C ６ - Alkyl is cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups. and C ３ -C ８ -Cycloalkyl includes halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C １ -C ６ - Alkyl, C １ -C ６ - Haloalkyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, C １ -C ６ - Alkoxycarbonyl, C １ -C ６ - Haloalkoxycarbonyl, C ２ -C ６ - Alkenil, C ３ -C ８ -Cycloalkyl, and C ３ -C ８ -Optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, R ２１ , R ２２ , R ２３ , and R ２４ Hydrogen and C are independent of each other. １ -C ６ - Alkyl or C １ -C ６ - It is a haloalkyl, C １ -C ６ - Alkyl and C １ -C ６ - Haloalkyls are cyano, hydroxyl, C １ -C ６ - Alkoxy, C １ -C ６ - Haloalkoxy, - O-Si (C １ -C ６ -Alkyl) ３ , -Si(C １ -C ６ -Alkyl) ３ , C ３ -C ８ -Cycloalkyl, and C ３ -C ８ - Further optionally substituted with 1 to 3 substituents independently selected from the group consisting of halocycloalkyl groups, or Two substituents R ７ They become C together with the carbon atoms to which they are bonded. ３ -C ８ Compounds (forming a cycloalkyl ring), Alternatively, their N-oxides, salts, or solvates, or solvates of the salts or N-oxides thereof.

Images