Microbiocidal compounds, their use, agrochemical composition and method of control and prevention of infestation of useful plants
Patent Information
- Application Number
- BR112021023888
- Authority / Receiving Office
- BR · BR
- Patent Type
- Patents
- Current Assignee / Owner
- Publication Date
- 2026-09-15
Abstract
Description
Microbiocidal compounds, their use, agrochemical composition, and methods for controlling and preventing infestation of useful plants.
[0001] The invention relates to microbicidal alkoxypyridine and alkoxypyrimidine derivatives, for example, as active ingredients, which have microbiocidal activity, in particular fungicidal activity. The invention also relates to the preparation of these alkoxypyridine and alkoxypyrimidine derivatives, to agrochemical compositions comprising at least one of the alkoxypyridine and alkoxypyrimidine derivatives, and to the uses of the alkoxypyridine and alkoxypyrimidine derivatives or their compositions in agriculture or horticulture for the control or prevention of infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, preferably fungi.
[0002] WO 2010 / 012793 and WO 2017 / 207362 describe thiazole derivatives as pesticide agents.
[0003] According to the present invention, a compound of formula (I) is provided: (I) in which A is N or CH; R1 is hydrogen, cyano, formyl, C1C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1C6 haloalkylcarbonyl, C1-C6 alkoxy C1-C6 alkylcarbonyl, C3 Petition 870250055585, dated 01 / 07 / 2025, page 15 / 501 2 / 236 Cecycloalkylcarbonyl, C1-CealkoxyC1-C3alkoxycarbonyl, C1Cealkoxyoxalyl, C1-CealkoxycarbonylC1-C4alkylCiCealkoxycarbonyl, C2-Cealkenyloxycarbonyl, or C2Cealkynyloxycarbonyl; R2 is hydrogen, C1-Cealkyl, C1-Cehaloalkyl, halogen, hydroxy, C1-Cealkoxy, C1-Cehaloalkoxy, C3-Cecycloalkyloxy, C3-Cehalocycloalkyloxy, C2-Cealkenyloxy, C2-Cehaloalkenyloxy, C2-Cealkynyloxy, C2-Cehaloalkynyloxy, C1-Cecyanoalkyloxy, C1-CealkoxyC1-C3alkoxy, C1-CealkoxyC1-C2alkyl, C2-Cealkynyl, C2-Cehaloalkynyl, or C3CecycloalkylC1-C2alkoxy; R3 is hydrogen, C1-Cealkyl, C1-Cehaloalkyl, halogen, hydroxy, C1-Cealkoxy, C1-Cehaloalkoxy, C3-Cecycloalkyloxy, C3-Cehalocycloalkyloxy, C2-Cealkenyloxy, C2-Cehaloalkenyloxy, C2-Cealkynyloxy, C2-Cehaloalkynyloxy, C1-Cecyanoalkyloxy, C1-CealkoxyC1-C3alkoxy, C1-CealkoxyC1-C2alkyl, C1-CealkoxyC1-C2alkylcarbonyloxy, C2-Cealkynyl, C2-Cehaloalkynyl, or C3-CecycloalkylC1-C2alkoxy; R4 is C1-C5 alkyl, C1-C5 shaloalkyl, C1-C5alkoxy, C3-C5alkynyl, C3-C5cycloalkyl, C3-C5cycloalkylC1-C2alkyl, phenyl, phenylC1-C3alkyl, phenoxyC1-C3alkyl, heteroaryl, heteroarylC1-C2alkyl, heteroarylC1-C2alkoxy-iminoC1-C2alkyl, wherein the heteroaryl is a 5- or β-membered aromatic monocyclic ring comprising i, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclylC1-C2alkyl, wherein the heterocyclyl is a 4-, 5 or β-membered non-aromatic monocyclic ring comprising i, 2 or 3 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl moieties, phenyl, heteroaryl or Petition 870250055585, dated 01 / 07 / 2025, p. 16 / 501 3 / 236 heterocyclines are each optionally substituted with 1 to 3 groups represented by R6 or 1 group represented by R7; and where R4 is a substituted heterocycline, these rings may contain a sulfonyl group (S(O)2); or R4 is a 6- to 10-membered annular ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N, O, and S, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene ligand; or R4 is a 5- to 10-membered non-aromatic spirocyclic carbobi- or carbotricyl ring system, optionally comprising 1, 2, 3, 4 or 5 heteroatoms individually selected from N, O and S, optionally substituted with 1 to 3 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene linker; R5 is C1-C8 alkyl, hydroxyC1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C2 alkyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, heterocyclyl, wherein heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring or a 9- to 10-membered non-aromatic bicyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R9; Petition 870250055585, dated 01 / 07 / 2025, p. 17 / 501 4 / 236 R6 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, cyano, or C1-C4 haloalkoxy; R7 is C1-C4 alkylsulfonyl, C3-C5 cycloalkyl, phenyl, benzyl, phenoxy or pyridyl, wherein each cycloalkyl, phenyl or pyridyl group is optionally replaced by a group represented by R8; R8 is a halogen or C1-C4 haloalkyl; R9 is halogen, cyano, benzyl, C1-C4 alkyl, C1-C4 alkoxy, or C1-C4 haloalkyl; either a salt of it or an N-oxide.
[0004] Surprisingly, it was discovered that the new compounds of formula (I) have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases caused by fungi.
[0005] According to a second aspect of the invention, an agrochemical composition is provided comprising an effective amount in terms of fungicide of a compound of formula (I) according to the present invention. Such an agricultural composition may further comprise at least one additional active ingredient and / or a diluent or carrier.
[0006] According to a third aspect of the invention, a method is provided for controlling or preventing the infestation of useful plants by phytopathogenic microorganisms, wherein an effective amount in terms of fungicides of a compound of formula (I), or a composition comprising this compound as an active ingredient, is applied to the plants, their parts or their locus.
[0007] According to a fourth aspect of the invention, the use of a compound of formula (I) is provided. Petition 870250055585, dated 01 / 07 / 2025, p. 18 / 501 5 / 236 as a fungicide. According to this particular aspect of the invention, the use may or may not include methods for treating the human or animal body by surgery or therapy.
[0008] Where substituents are indicated as being “optionally substituted”, this means that they may or may not carry one or more identical or different substituents, for example, one, two or three R6 substituents. For example, C1-C8 alkyl substituted with 1, 2 or 3 halogens may include, but is not limited to, CH2Cl, -CHCl2, -CCl3, -CH2F, -CHF2, -CF3, -CH2CF3 or -CF2CH3 groups. As another example, C1-C6 alkoxy substituted with 1, 2 or 3 halogens may include, but is not limited to, CH2ClO-, CHCl2O-, CCl3O-, CH2FO-, CHF2O-, CF3O-, CF3CH2O- or CH3CF2O- groups.
[0009] As used here, the term “cyan” means a -CN group.
[0010] As used herein, the term “halogen” refers to fluorine (fluoro), chlorine (chlorine), bromine (bromine) or iodine (iodine).
[0011] As used in this document, the term “formila” means a -C(O)H group.
[0012] As used in this document, the term “acetyl” means a -C(O)CH3 group.
[0013] As used herein, the term “C1-C8 alkyl” refers to a linear or branched hydrocarbon chain radical consisting merely of carbon and hydrogen atoms, containing no unsaturation, having from one to eight carbon atoms, and which is attached to the rest of the molecule by a single bond. “C1-C6 alkyl”, “C1-C4 alkyl” and “C1-C3 alkyl” should be interpreted accordingly. Examples Petition 870250055585, dated 01 / 07 / 2025, p. 19 / 501 6 / 236 of C1-C2 alkyl include, but are not limited to, methyl, ethyl, n-propyl, and their isomers, for example, isopropyl. A C1-C2 alkylene group refers to the corresponding definition of C1-C2 alkyl, except that such a radical is linked to the rest of the molecule by two single bonds. The term C1-C2 alkylene should be interpreted accordingly. Examples of C1-C2 alkylene include, but are not limited to, -CH2-, CH2CH2-, and -(CH2)3-.
[0014] As used in this document, the term C1-C2haloalkyl refers to a C1-C2alkyl radical as generally defined above substituted with one or more identical or different halogen atoms. The terms C1-C4haloalkyl and C1-C4haloalkyl should be interpreted accordingly. Examples of C1-C2haloalkyl include, but are not limited to, trifluoromethyl.
[0015] As used herein, the term Ci-Csalkoxy refers to a radical of the formula -ORa where Ra is a Ci-Csalkyl radical as generally defined above. The terms CiCealkoxy, Ci-C4alkoxy and Ci-C3alkoxy should be interpreted accordingly. Examples of Ci-Csalkoxy include, but are not limited to, methoxy, ethoxy, methylethoxy (isopropoxy) and propoxy.
[0016] As used herein, the term C2C6alkenyl refers to a linear or branched hydrocarbon chain radical group consisting only of carbon and hydrogen atoms, containing at least one double bond which may have an (E) or (Z) configuration, possessing from two to six carbon atoms, which is linked to the rest of the molecule by a single bond. The term C2-C3alkenyl is to be interpreted accordingly. Examples of C2 Petition 870250055585, dated 01 / 07 / 2025, p. 20 / 501 7 / 236 Cealkenyl groups include, but are not limited to, ethenyl (vinyl), prop-1-enyl, prop-2-enyl (allyl), but-1-enyl.
[0017] As used in this document, the term C2-C6alkenyloxy refers to a radical of formula -ORa, where Ra is a C2-Calkenyl radical as generally defined above.
[0018] As used herein, the term “C2-C3-alkynyl” refers to a radical group of a linear or branched hydrocarbon chain consisting only of carbon and hydrogen atoms, containing at least one triple bond, having two to six carbon atoms, and which is linked to the rest of the molecule by a single bond. The term “C2-C3-alkynyl” is to be interpreted accordingly. Examples of C2-C3-alkynyl include, but are not limited to, ethinyl, prop-1-ynyl, but-1-ynyl.
[0019] As used in this document, the term C2-C6alkynyloxy refers to a radical of formula -ORa, where Ra is a C2-Calkynyl radical as defined in general above.
[0020] As used herein, the term C3Cscycloalkyl refers to a radical that is a system of saturated monocyclic rings containing 3 to 8 carbon atoms. The terms C3-C6cycloalkyl and C3-C4cycloalkyl should be interpreted accordingly. Examples of C3C6cycloalkyl include, but are not limited to, cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclobutyl, 1-methylcyclobutyl, 1,1-dimethylcyclobutyl, 2-methylcyclobutyl, and 2,2-dimethylcyclobutyl.
[0021] As used in this document, the term C3-C8cycloalkylC1-C2alkyl refers to a C3 ring Petition 870250055585, dated 01 / 07 / 2025, p. 21 / 501 8 / 236 Cscycloalkyl linked to the rest of the molecule by a C1C2alkylene ligand as defined above.
[0022] As used in this document, the term phenylCi-C3alkyl refers to a phenyl ring linked to the rest of the molecule by a Ci-C3alkylene ligand as defined above.
[0023] As used herein, the term heteroaryl refers to a radical of a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S. Examples of heteroaryls include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidinyl, or pyridyl.
[0024] As used in this document, the term heteroarylC1-C2alkyl refers to a heteroaryl ring linked to the rest of the molecule by a C1-C2alkylene ligand as defined above.
[0025] As used in this document, the term heterocyclyl refers to a stable non-aromatic monocyclic ring with 4, 5, or 6 members comprising 1, 2, or 3 heteroatoms, wherein the heteroatoms are individually selected from N, O, and S. The heterocyclyl radical may be linked to the rest of the molecule through a carbon atom or heteroatom. Examples of heterocyclyls include, but are not limited to, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuryl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, Petition 870250055585, dated 01 / 07 / 2025, p. 22 / 501 9 / 236 piperazinyl, morpholinyl, dioxolanyl, dithiolanyl and thiazolidinyl.
[0026] As used in this document, the term heterocyclyl C1-C2 alkyl refers to a heterocyclyl ring linked to the rest of the molecule by a C1-C2 alkylene ligand as defined above.
[0027] As used in this document, a spirocyclic carbobi- or carbotri-cyclyl ring is a non-aromatic bicyclic ring system comprising two rings linked at a carbon atom, i.e., sharing a carbon atom. Examples of a spirocyclic carbobi- or carbotri-cyclyl ring system include, but are not limited to, spiro[3.3]heptanyl, spiro[3.4]octanyl, spiro[4.5]decanyl, spiro[cyclobutan-1,2'-indanyl], or spiro[cyclopentane-1,2'-tetralynyl].
[0028] As used in this document, the term C1-Cgalkylcarbonyl refers to a radical of the formula C(O)Ra where Ra is a C1-C6alkyl radical, as generally defined above.
[0029] As used in this document, the term C1-C6-alkoxyC1-C6alkylcarbonyl refers to a radical of the formula -C(O)RaORb, where Rb is a C1-C6alkyl radical, as generally defined above, and Ra is a C1-C6alkylene radical, as generally defined above.
[0030] As used in this document, the term C1-Cghaloalkylcarbonyl refers to a radical of the formula -C(O)Ra where Ra is a C1-C6haloalkyl radical, as generally defined above. Petition 870250055585, dated 01 / 07 / 2025, p. 23 / 501 10 / 236
[0031] As used in this document, the term C3-C6cycloalkylcarbonyl refers to a radical of the formula -C(O)Ra where Ra is a C3-C6cycloalkyl radical, as generally defined above.
[0032] As used in this document, the term C1-Cgalkoxycarbonyl refers to a radical of the formula C(O)ORa where Ra is a C1-C6alkyl radical, as generally defined above.
[0033] As used herein, the term C1Cgalcoxyoxalyl refers to the radical -C(O)C(O)ORa, where Ra is a C1-C6 alkyl radical as generally defined above.
[0034] As used in this document, the term C2-C6alkenyloxycarbonyl refers to a radical of the formula -C(O)ORa, where Ra is a C2-C6alkenyl radical, as generally defined above.
[0035] As used in this document, the term C2-C6alkynyloxycarbonyl refers to a radical of the formula -C(O)ORa where Ra is a C2-C6alkynyl radical, as generally defined above.
[0036] As used in this document, the term phenylcarbonyl refers to a radical of the formula -C(O)Ra, where Ra is a phenyl radical.
[0037] As used in this document, the term phenoxycarbonyl refers to a radical of formula -C(O)ORa where Ra is a phenyl radical.
[0038] As used in this document, the term heteroarylcarbonyl refers to a radical of formula C(O)Ra, where Ra is a heteroaryl radical, as generally defined above. Petition 870250055585, dated 01 / 07 / 2025, p. 24 / 501 11 / 236
[0039] The presence of one or more possible stereogenic atoms in a compound of formula (I) means that the compounds can occur in optically isomeric forms, that is, enantiomeric or diastereomeric forms. Atropisomers can also occur as a result of restricted rotation around a single bond. Formula (I) is intended to include all these possible isomeric forms and mixtures thereof. The present invention includes all these possible isomeric forms and mixtures thereof for a compound of formula (I). Similarly, formula (I) is intended to include all possible tautomers. The present invention includes all possible tautomeric forms for a compound of formula (I).
[0040] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as an N-oxide, or in saline form, for example, in an agronomically usable saline form.
[0041] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. They are described, for example, in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra, CRC Press, Boca Raton (1991).
[0042] The following list provides definitions, including preferred definitions, for substituents A, R1, R2, R3, R4, R5, R6, R7, R8 and R9 with reference to compounds of formula (I). For any of these substituents, any of the definitions given below may be combined with any definition of any other substituent given below or elsewhere in this document. Petition 870250055585, dated 01 / 07 / 2025, p. 25 / 501 12 / 236
[0043] A is N or CH. In one set of modalities, A is N. In another set of modalities, A is CH.
[0044] R1 is hydrogen, cyano, formyl, C1Cg alkylcarbonyl, C1-C galkoxycarbonyl, C1C6 haloalkylcarbonyl, C1-C6 alkoxyC1-C6 alkylcarbonyl, C3C6 cycloalkylcarbonyl, C1-C6 alkoxyC1-C3 alkoxycarbonyl, C1Ce alkoxyoxalyl, C1-C6 alkoxycarbonylC1-C4 alkylC1C6 alkoxycarbonyl, C2-C6 alkenyloxycarbonyl, or C2C galquinyloxycarbonyl. Preferably, R1 is hydrogen, cyano, C1-C6 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 haloalkylcarbonyl, C1-C4 alkoxyC1-C3 alkylcarbonyl, C3C6 cycloalkylcarbonyl, C1-C4 alkoxyC1-C2 alkoxycarbonyl, C2C4 alkenyloxycarbonyl, or C2-C4 alkyloxycarbonyl. More preferably, R1 is hydrogen, cyano, C1C6 alkylcarbonyl, or C1-C4 alkoxyC1-C3 alkylcarbonyl. Even more preferably, R1 is hydrogen, cyano, C1C3 alkylcarbonyl, or C1-C2 alkoxyC1-C2 alkylcarbonyl. Even more preferably, R1 is hydrogen, cyano, acetyl, methoxycarbonyl, or methoxymethylcarbonyl. Most preferably, R1 is hydrogen, cyano, acetyl, or methoxymethylcarbonyl.Even more preferably, R1 is hydrogen, cyano, or methoxymethylcarbonyl. Most preferably, R1 is hydrogen.
[0045] R2 is hydrogen, C1-Ce alkyl, C1-Ce haloalkyl, halogen, hydroxy, C1-C6 alkoxy, C1— Cehaloalkoxy, C3—C6cycloalkyloxy, C3—C6halocycloalkyloxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, C2C6haloalkynyloxy, C1-C6cyanoalkyloxy, C1-C6alkoxyC1C3alkoxy, C1-C6alkoxyC1-C2alkyl, C2-C6alkynyl, C2Petition 870250055585, of 07 / 01 / 2025, p. 26 / 501 13 / 236 Cehaloalkynyl, or C3-CecycloalkylCi-C2alkoxy. Preferably, R2 is hydrogen, C1-Cealkyl, C1-Cehaloalkyl, halogen, hydroxy, C1-Cealkoxy, C1-Cehaloalkoxy, C3-Cecycloalkyloxy, C2-Cealkenyloxy, C2-C6haloalkenyl6xy, C2-C6alkynyl6xy, C2-C6haloalkynyl6xy, C1-C6alkoxyC1-C3alkoxy, C1-CealkoxyC1-C2alkyl, C2-Cealkynyl, or C2-Cehaloalkynyl. More preferably, R2 is hydrogen, C1-Cealkyl, C1-C4haloalkyl, halogen, hydroxy, C1-C6alkoxy, C1-C3haloalkoxy, C3-C6cycloalkyloxy, C2-C5alkenyloxy, C2-C5haloalkenyloxy, C2-C5alkynyloxy, C1-C4alkoxy, C1-C3alkoxy, C1-C4alkoxy, C1-C2alkyl, or C2-C5alkynyl. Even more preferably, R2 is hydrogen, C1-C4alkyl, C1-C3haloalkyl, halogen, hydroxy, C1-C4alkoxy, C1-C3haloalkoxy, C3-C4alkenyloxy, C3-C4alkynyloxy, C1-C2alkoxy, C1-C2alkoxy, C1-C2alkoxy, C1-C2alkyl, or C3-C5alkynyl. Even more preferably, R2 is hydrogen, C1-C4alkyl, halogen, or C1-C4alkoxy. Or even more preferably, R2 is hydrogen, methyl, chlorine, bromine, fluorine, methoxy, or ethoxy. Most preferably, R2 is hydrogen.
[0046] R3 is hydrogen, C1-Cealkyl, C1-Cehaloalkyl, halogen, hydroxy, C1-Cealkoxy, C1- Cehaloalkoxy, C3-Cecycloalkyloxy, C3-Cehalocycloalkyloxy, C2-C6alkenyloxy, C2-Cehaloalkenyloxy, C2-Cealkynyloxy, C2Cehaloalkynyloxy, Ci-Cecianoalkyloxy, Ci-CealkoxyCiC3alkoxy, Ci-CealkoxyCi-C2alkyl, Ci-CealkoxyCiC2alkylcarbonyloxy, C2-Cealkynyl, C2-Cehaloalkynyl, or C3-CecycloalkylCi-C2alkoxy.
[0047] Preferably, R3 is hydrogen, C1-Ce-alkyl, C1-Ce-haloalkyl, halogen, hydroxy, C1-Ce-alkoxy, Petition 870250055585, dated 01 / 07 / 2025, page 27 / 501 14 / 236 Ci-Cehaloalkoxy, C3-C6cycloalkyloxy, C3Cehalocycloalkyloxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, C2-C6haloalkynyloxy, Ci-Cecianoalkyloxy, Ci-C6alkoxyCi-C3alkoxy, Ci-CgalkoxyCi-C2alkyl, Ci-CgalkoxyCiC2alkylcarbonyloxy, C2-Cgalkynyl, or C2-Cghaloalkynyl. More preferably, R3 is hydrogen, C1-C1 alkyl, C1-C4 haloalkyl, halogen, hydroxy, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyloxy, C2-C6 alkenyloxy, C2-C5 haloalkenyloxy, C2-C6 alkynyloxy, C2-C5 haloalkynyloxy, C1-C4 alkoxy C1-C3 alkoxy, C1-C4 alkoxy C1-C2 alkyl, C1-C6 alkoxy C1-C2 alkylcarbonyloxy, or C2-C5 alkynyl. Even more preferably, R3 is hydrogen, C1-C4 alkyl, halogen, hydroxy, C1-C4 alkoxy, C1-C3 haloalkoxy, C3-C6 cycloalkyloxy, C3-C5 alkenyloxy, C3-C5 alkynyloxy, or C1-C4 alkoxy C1-C2 alkylcarbonyloxy.More preferably, R3 is hydrogen, methyl, chlorine, bromine, fluorine, hydroxy, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, cyclopropoxy, allyloxy, propargyloxy or methoxymethylcarbonyloxy. More preferably, R3 is hydroxy, methoxy, ethoxy, isopropoxy, allyloxy or methoxymethylcarbonyloxy.
[0048] R4 is C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 alkoxy, C3-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C2 alkyl, phenyl, phenyl C1-C3 alkyl, phenoxy C1-C3 alkyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryl C1-C2 alkoxy-imino C1-C2 alkyl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, 3 or 4 heteroatoms individually selected from N, O and S, heterocyclyl, heterocyclyl C1-C2 alkyl, wherein the heterocyclyl is a ring Petition 870250055585, dated 01 / 07 / 2025, page 28 / 501 15 / 236 non-aromatic monocyclic compound of 4, 5 or 6 members comprising 1, 2, or 3 heteroatoms individually selected from N, O, and S, in which the cycloalkyl, phenyl, heteroaryl, or heterocyclyl moieties are each optionally substituted with 1 to 3 groups represented by R6 or 1 group represented by R7; and where, when R4 is a substituted heterocyclyl, these rings may contain a sulfonyl group (S(O)2); or R4 is a 6- to 10-membered annular ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N, O, and S, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene ligand; or
[0049] R4 is a 5 to 10 membered non-aromatic spirocyclic carbobi- or carbotri-cyclyl ring system, optionally comprising 1, 2, 3, 4 or 5 heteroatoms individually selected from N, O and S, optionally substituted with 1 to 3 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene linker.
[0050] Preferably, R4 is C1-C8 alkyl, C3-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C2 alkyl, phenylC1-C3 alkyl, phenoxyC1-C3 alkyl, heteroaryl, heteroarylC1-C2 alkyl, heteroarylC1-C2 alkoxy-iminoC1-C2 alkyl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from N, O, and S, heterocyclyl, heterocyclylC1-C2 alkyl, wherein the heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring Petition 870250055585, dated 01 / 07 / 2025, p. 29 / 501 16 / 236 members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted with 1 to 3 groups represented by R6 or 1 group represented by R7; and wherein when R4 is a substituted heterocyclyl, these rings may contain a sulfonyl group (S(O)2); or
[0051] R4 is a 7- to 10-membered annular ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N, O, and S, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene ligand; or
[0052] R4 is a 6- to 10-membered non-aromatic spirocyclic carbobi- or carbotri-cyclyl ring system, optionally comprising 1, 2, 3, 4 or 5 heteroatoms individually selected from N, O and S, optionally substituted with 1 to 3 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene linker.
[0053] More preferably, R4 is C1-C8 alkyl, C3-C8 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C2 alkyl, phenyl C1-C3 alkyl, phenoxy C1-C3 alkyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryl C1-C2 alkoxy-imino C1-C2 alkyl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from N and O, heterocyclyl, heterocyclyl C1-C2 alkyl, wherein heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from N and O. Petition 870250055585, dated 01 / 07 / 2025, p. 30 / 501 17 / 236 selected from N, O, and S, wherein the cycloalkyl, phenyl, heteroaryl, and heterocyclyl moieties are each optionally substituted with 1 to 3 groups represented by R6 or 1 group represented by R7; and wherein when R4 is a substituted heterocyclyl, these rings may contain a sulfonyl group (S(O)2); or
[0054] R4 is a 7- to 9-membered annular ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene ligand; or
[0055] R4 is a 6- to 9-membered non-aromatic spirocyclic carbocyclyl ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 to 3 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene linker.
[0056] Even more preferably, R4 is C1-C8 alkyl, C3-C7 alkynyl, C3-C4 cycloalkyl, C3-C4 cycloalkyl C1-C2 alkyl, phenyl C1-C3 alkyl, phenoxy C1-C3 alkyl, heteroaryl, heteroaryl C1-C2 alkyl, heteroaryl C1-C2 alkoxy-imino C1-C2 alkyl, wherein the heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from N and O, heterocyclyl, heterocyclyl C1-C2 alkyl, wherein the heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from N, O, and S, and wherein the cycloalkyl, phenyl, heteroaryl, and heterocyclyl moieties are, each Petition 870250055585, dated 01 / 07 / 2025, p. 31 / 501 18 / 236 one, optionally substituted with 1 or 2 groups represented by R6 or 1 group represented by R7; and where when R4 is a substituted heterocycline, these rings may contain a sulfonyl group (S(O)2); or R4 is a 7- to 9-membered annular ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene ligand; or
[0057] R4 is a 6- to 9-membered non-aromatic spirocyclic carbocyclyl ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1C2alkylene ligand.
[0058] Even more preferably, R3 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1,5-dimethylhexyl, 4,4-dimethylpent-2-ynyl, cyclopropyl optionally substituted with 1 group represented by R6 or 1 group represented by R7, cyclobutyl optionally substituted with 1 or 2 groups represented by R6 or 1 group represented by R7, cyclopropylmethyl optionally substituted with 1 group represented by R6 or 1 group represented by R7, C1-C3 phenyl alkyl optionally substituted with 1 or 2 groups represented by R6 or 1 group represented by R7, C1-C3 phenoxy alkyl optionally substituted with 1 or 2 groups represented by R6, C1-C2 heteroaryl alkyl, C1-C2 heteroaryl alkoxy-imino C1-C2 alkyl, wherein the heteroaryl is a ring Petition 870250055585, dated 01 / 07 / 2025, page 32 / 501 19 / 236 aromatic monocyclic ring of 5 or 6 members comprising 1 or 2 heteroatoms individually selected from N and O, and wherein the heteroaryl moieties are optionally substituted with 1 or 2 groups represented by R6 or 1 group represented by R7, heterocyclyl, wherein the heterocyclyl is a non-aromatic monocyclic ring of 5 or 6 members comprising a single heteroatom selected from N and O, heterocyclyl C1-C2alkyl, wherein the heterocyclyl is a non-aromatic monocyclic ring of 5 or 6 members comprising 1, 2 or 3 heteroatoms individually selected from N and O, and wherein the heterocyclyl moieties are optionally substituted with a group represented by R6 or 1 group represented by R7; and wherein when R4 is a substituted heterocyclyl, these rings may contain a sulfonyl group (S(O)2); or R4 is a 7- to 9-membered annular ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene ligand; or R4 is a 6- to 9-membered non-aromatic spirocyclic carbocyclyl ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1C2alkylene ligand.
[0059] Even more preferably, R4 is t-butyl, isopentyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, Petition 870250055585, dated 01 / 07 / 2025, p. 33 / 501 20 / 236 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1,5-dimethylhexyl, 4,4-dimethylpent-2ynyl, 1-methylcyclopropyl, 1-methylcyclopentyl, 1-ethylcyclobutyl, 1-isopropylcyclobutyl, 1-tert-butylcyclobutyl, 1-cyanocyclopentyl, 3-methyltetrahydrofuran-3-yl, 1-methylcyclohexyl, 1-cyclohexylcyclopropyl, 4-fluorophenylcyclopropyl, (4chlorophenyl)methylcyclopropyl, 1-methylcyclobutyl, 3methoxyoxetan-3-yl, 2,2-dimethylcyclobutyl, 1cyanocyclobutyl, 1-cyclobutylcyclobutyl, 4fluorophenoxycyclobutyl, 1-trifluoromethylcyclopropylmethyl, (5-(trifluoromethyl)-2-pyridyl)cyclopropylmethyl, (6-chloro3-pyridyl)cyclopropylmethyl, (6-chloro-2pyridyl)cyclobutyl, (6-chloro-3-pyridyl)cyclobutyl, benzyl, phenoxybenzyl, phenylethyl, 4-trifluoromethoxyphenylethyl, 2-phenylpropyl, 4-chlorobenzyl, 3,5-difluorobenzyl, 4-fluorophenoxyethyl, 3,5difluorophenoxy-1-methylethyl, (4-chlorophenyl)cyclobutyl, 2,4-dichlorophenoxyethyl, 3,5-bis(trifluoromethyl)phenyl, benzylimidazol-4-yl,4-(difluoromethyl)-1-methylpyrazole-3ylmethyl, 3,5-dicloro-4-pyridylmethyl, 1-(5-methyloxazol-2yl)ethyl, 2-trifluoromethylpyrimidine-5-yl, (3,5-dicloro-2pyridyl)-2-ethoxiimino-ethyl, 1-isopropylsulfonyl-4piperidinyl, 1,1-dioxotian-4-yl, 3-cianotietan-3-yl, 5-cyclopropyltetra-hydrofuran-3-yl, 3-methyltetra-hydrofuran3-ylmethyl, 1-tetra-hydropyran-4-ylethyl, 2-methyltraisol-4-ylmethyl, 5-(trifluoromethyl)indan-1-yl, 6(trifluoromethyl)indan-1-yl, 1-methylpyrazolo[3,4-b]pyridine3-yla, 2,3-di-hydrobenzofuran-3-ylmethyla, 2,2-difluoro-1,3benzodioxol-4-ylmethyla, espiro[3,4]octane-3-yla, 8-methyl-5Petição 870250055585, de 01 / 07 / 2025, page. 34 / 501, 21 / 236 oxaspiro[3.5]nonane-8-to, 2-oxabiciclo[3.3]heptane-6-to, 7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-6-yl, 2oxabicyclo[3.2.0]heptan-7-yl, or 4-oxaspiro[2.3]heptan-6-yl.
[0060] Even more preferably, R4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1,5-dimethylhexyl, 4,4-dimethylpent-2-ynyl, 1-methylcyclopropyl, 1-cyclohexylcyclopropyl, 4-fluorophenylcyclopropyl, (4chlorophenyl)methylcyclopropyl, 2,2-dimethylcyclobutyl, 4fluorophenoxycyclobutyl, 1-trifluoromethylcyclopropylmethyl, (5-(trifluoromethyl)-2-pyridyl)cyclopropylmethyl, (6-chloro3-pyridyl)cyclopropylmethyl, benzyl, phenoxybenzyl, 4trifluoromethoxyphenylethyl, 2-phenylpropyl, 4-chlorobenzyl, 3,5-difluorobenzyl, 4-fluorophenoxyethyl, 3,5difluorophenoxy-1-methylethyl, 2,4-dichlorophenoxyethyl, benzylimidazol-4-yl, 4-(difluoromethyl)-1-methylpyrazol-3-ylmethyl, 3,5-dichloro-4-pyridylmethyl, 1-(5-methyloxazol-2-yl)ethyl, 2-trifluoromethylpyrimidin-5-yl, (3,5-dichloro-2pyridyl)-2-ethoxyimino-ethyl, 1-isopropylsulfonyl-4piperidinyl, 1,1-dioxothian-4-yl, 5cyclopropyltetrahydrofuran-3-yl,3-methyltetrahydrofuran-3-ylmethyl, 1-tetra-hydropyran-4-ylmethyl, 2-methyltraisol-4-ylmethyl, 5-(trifluoromethyl)indan-1-ylmethyl, 6(trifluoromethyl)indan-1-ylmethyl, 1-methylpyrazole[3,4-b]pyridine3-ylmethyl, 2,3-di-hydrobenzofuran-3-ylmethyl, 2,2-difluoro-1,3benzodioxol-4-ylmethyl, espiro[3,4]octan-3-ylmethyl, 8-methyl-5oxaespiro[3.5]nonan-8-ylmethyl, 2-oxabiciclo[3.3]heptan-6-ylmethyl, 7,7-dimethyl-2-oxabiciclo[3.2.0]heptan-6-ila, 2oxabiciclo[3.2.0]heptan-7-ila or 4-oxaspiro[2,3]heptan-6ila. Petição 870250055585, at 01 / 07 / 2025, pág. 35 / 501 22 / 236
[0061] Therefore, R4é t-butyla, isopentila, 2,2-dimethylpropyla, 1-methylciclopropyla, 2,2-dimethylciclobutyla or espiro[3.4]octane-3-la.
[0062] In one set of embodiments, R4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1,1,2-trimethylpropyl, 1-methylcyclopropyl, 1-methylcyclobutyl, 1-ethylcyclobutyl, 1-isopropylcyclobutyl, 1-tert-butylcyclobutyl, 1-cyclobutylcyclobutyl, 2,2-dimethylcyclobutyl, 1-methylcyclopentyl, or spiro[3.4]octan-3-yl. In another set of embodiments, R4 is t-butyl, 1,1,2-trimethylpropyl, 1-methylcyclobutyl, 1-ethylcyclobutyl, 1-isopropylcyclobutyl, 1-tert-butylcyclobutyl, 1-cyclobutylcyclobutyl, 2,2-dimethylcyclobutyl, or 1-methylcyclopentyl.
[0063] R5 is C1-C8 alkyl, hydroxyC1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C2 alkyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, heterocyclyl, wherein heterocyclyl is a 4-, 5- or 6-membered non-aromatic monocyclic ring or a 9- to 10-membered non-aromatic bicyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R9. Preferably, R5 is C1-C6 alkyl, hydroxyC1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C2 alkyl, phenyl, heteroaryl, where heteroaryl is a 5- or 6-membered aromatic monocyclic ring. Petition 870250055585, dated 01 / 07 / 2025, p. 36 / 501 23 / 236 comprising 1 or 2 heteroatoms individually selected from N, O and S, heterocyclyl, wherein the heterocyclyl is a 5 or 6 membered non-aromatic monocyclic ring or a 9 to 10 membered non-aromatic bicyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R9.More preferably, R5 is C1-C3 alkyl, hydroxyC1-C4 alkyl, C3-C4 cycloalkyl, C3-C4 cycloalkylC1-C2 alkyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, heterocyclyl, wherein heterocyclyl is a 9- to 10-membered non-aromatic bicyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1, 2 or 3 (preferably 1 or 2), which may be the same or different, selected from R9.Even more preferably, R5 is C1-C6 alkyl, 2,3-dihydroxypropyl, C3-C4 cycloalkyl, cyclopropylmethyl, cyclobutylmethyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N and S, heterocyclyl, wherein heterocyclyl is a 9- to 10-membered non-aromatic bicyclic ring comprising 1 or 2 oxygen atoms, and wherein the phenyl and heteroaryl moieties are each optionally substituted by 1, 2 or 3 (preferably 1 or 2). Petition 870250055585, dated 01 / 07 / 2025, p. 37 / 501 24 / 236 substitutes, which may be the same or different, selected from R9.
[0064] In a combination of modes, R5 is 2,3di-hidroxypropyl, cyclobutyl, cyclopropylmethyl, phenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 3methylphenyl, 4-methylphenyl, 3-ethylphenyl, 3-methoxyphenyl, 3cyanophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,4dichlorophenyl, 3,5-dimethylphenyl, 3,5-dimethoxyphenyl, 3fluoro-4-methylphenyl, 3-chloro-4-methylphenyl, 3-chloro-5fluorophenyl, 4-chloro-3,5-difluorophenyl, 4-chloro-3fluorophenyl, 4-Chloro-3-methylphenyla, 3-cyano-5-methylphenyla, 3-cyano-5-fluorophenyla, 4-cyano-3-fluorophenyla, 3,4,5trifluorophenyla, 4-trifluoromethylphenyla, 3-fluoro-4(trifluoromethyl)phenyla, pyridin-4-yla, 2-fluoropyridin-4-yla, 2-chloropyridin-4-yla, 2,6-difluoropyridin-4-yla, 2,6dichloropyridin-4-yla, pyridin-3-yla, 6-fluoropyridin-3-yla, 5-fluoropyridin-3-yla, 6-chloropyridin-3-yla, 5chloropyridin-3-yla, 5-(trifluoromethyl)-pyridin-3-yla, 2,6difluoro-3-iodopyridin-4-yla, isothiazol-4-yl, thiazol-2yl, pyrimidin-5-yl, benzofuran-5-yl, 1-benzilindazol-6yl, ou 1,3-benzodioxol-5-yl.,
[0065] In another set of modalities, R5é is 2,3-di-hydroxypropyl, cyclobutyl, cyclopropylmethyl, phenyl, 3-fluorophenyl, 3-chlorophenyl, 3-methylphenyl, 3methoxyphenyl, 3,5-difluorophenyl, 3,5- dichlorophenyl,
[0066] ; 3,5dimethylphenyl, 3,5-dimethoxyphenyl, pyridin-4-yl, 2fluoropyridin-4-yl, 2-chloropyridin-4-yl, 2,6difluoropyridin-4-yl, 2,6-dichloropyridin-4-yl, pyridin-3yl, 6-fluoropyridin-3-yl, 5-fluoropyridin-3-yl, 6chloropyridin-3-yl, 5-chloropyridin-3-yl, isothiazol-4-yl, Petition 870250055585, dated 01 / 07 / 2025, p. 38 / 5 25 / 236 thiazol-2-yl, pyrimidin-5-yl or 1,3-benzodioxol-5-yl. In a further set of embodiments, R5 is 2,3-dihydroxypropyl, cyclobutyl, cyclopropylmethyl, phenyl, 3,5-difluorophenyl, 2-fluoropyridin-4-yl, 2,6-difluoropyridin-4-yl, 2-chlorpyridin-4-yl, 2,6-difluoropyridin-4-yl, 5-fluoropyridin-3-yl, 6-fluoropyridin-3-yl, isothiazol-4-yl, thiazol-2-yl, pyrimidin-5-yl or 1,3-benzodioxol-5-yl. In yet another set of embodiments, R5 is 3,5-difluorophenyl, 2,6-difluoropyridin-4-yl, or isothiazol-4-yl.
[0066] In a preferred set of embodiments, R5 is 2,6-difluoropyridin-4-yl, 3,5-difluorophenyl, 2-fluoropyridin-4-yl, 3-fluorophenyl, or 3,4,5-trifluorophenyl.
[0067] R6 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, cyano, or C1-C4 haloalkoxy. Preferably, R6 is halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, cyano, or C1-C3 haloalkoxy. More preferably, R6 is halogen, C1-C3 alkyl, C1-C3 haloalkyl, cyano, or C1-C3 haloalkoxy. Even more preferably, R6 is chlorine, fluorine, methyl, difluoromethyl, trifluoromethyl, or cyano. More preferably still, R6 is methyl.
[0068] In a set of embodiments, R6 is halogen, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 haloalkyl, or C1-C4 haloalkoxy. Preferably, R6 is halogen, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, or C1-C3 haloalkoxy. More preferably, R6 is halogen, C1-C3 alkoxy, C1-C3 haloalkyl, or C1-C3 haloalkoxy. Even more preferably, R6 is chlorine, fluoro, methyl, Petition 870250055585, dated 01 / 07 / 2025, page 39 / 501 26 / 236 difluoromethyl, or trifluoromethyl. More preferably, R6 is methyl.
[0069] R7 is C1-C4 alkylsulfonyl, C3-C8 cycloalkyl, phenyl, benzyl, phenoxy, or pyridyl, wherein each cycloalkyl, phenyl, or pyridyl group is optionally replaced by 1 group represented by R Preferably, R7 is C1-C3 alkylsulfonyl, C3-C6 cycloalkyl, phenyl, benzyl, phenoxy, or pyridyl, wherein each cycloalkyl, phenyl, or pyridyl group is optionally replaced by 1 group represented by R8. Even more preferably, R7 is isopropylsulfonyl, cyclopropyl, cyclohexyl, phenyl, benzyl, phenoxy, or pyridyl, wherein each cycloalkyl, phenyl, or pyridyl group is optionally replaced by 1 group represented by R8.
[0070] R8 is a halogen or C1-C4 haloalkyl. Preferably, R8 is a halogen or a C1-C3 haloalkyl. More preferably, R8 is chlorine, fluorine, or trifluoromethyl.
[0071] R9 is halogen, cyano, benzyl, C1-C4 alkyl, C1-C4 alkoxy, or C1-C4 haloalkyl. Preferably, R9 is chlorine, fluorine, iodine, cyano, C1-C3 alkyl, C1-C3 alkoxy, or C1-C3 haloalkyl. More preferably, R9 is chlorine, fluorine, iodine, cyano, benzyl, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, isopropoxy, difluoromethyl, or trifluoromethyl. Even more preferably, R9 is chlorine, fluorine, or methyl. Most preferably, R9 is fluorine.
[0072] In one embodiment, R9 is halogen, C1-C4 alkyl, C1-C4 alkoxy, or C1-C4 haloalkyl. In a further embodiment, R9 is chlorine, fluorine, C1-C3 alkyl, C1-C3 alkoxy, or C1-C3 haloalkyl. In another embodiment, R9 is chlorine, fluorine, C1-C3 alkyl, C1-C3 alkoxy, or C1-C3 haloalkyl. Petition 870250055585, dated 01 / 07 / 2025, page 40 / 501 27 / 236 set of modalities, R9 is chlorine, fluorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, isopropoxy, difluoromethyl or trifluoromethyl.
[0073] In a compound of formula (I) according to the present invention, preferably: A is N or CH; R1 is hydrogen, cyano, C1-Ce alkyl carbonyl, or C1-C4alkoxyC1-C3alkylcarbonyl; R2 is hydrogen; R3 is hydrogen, C1-C4 alkyl, halogen, hydroxy, C1-C4 alkoxy, C1-C3 haloalkoxy, C3-C6 cycloalkyloxy, C3-C5 alkenyloxy, C3-C5 alkynyloxy, or C1-C4 alkoxy C1-C2 alkylcarbonyloxy; R4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1,5-dimethylhexyl, 4,4-dimethylpent-2-ynyl, cyclopropyl optionally substituted with 1 group represented by R6 or 1 group represented by R7, cyclobutyl optionally substituted with 1 or 2 groups represented by R6 or 1 group represented by R7, cyclopropylmethyl optionally substituted with 1 group represented by R6 or 1 group represented by R7, C1-C3 phenyl alkyl optionally substituted with 1 or 2 groups represented by R6 or 1 group represented by R7, C1-C3 phenoxy alkyl optionally substituted with 1 or 2 groups represented by R6 or 1 group represented by R7, C1-C3 phenoxy alkyl optionally substituted with 1 or 2 groups represented by R6, C1-C2 heteroaryl alkyl, C1-C2 heteroaryl alkoxy-imino 1C2alkyl, wherein the heteroaryl group is a 5- or 6-membered monocyclic aromatic ring comprising 1 or 2 heteroatoms individually selected from N and O, Petition 870250055585, dated 01 / 07 / 2025, p. 41 / 501 28 / 236 and wherein the heteroaryl moieties are optionally substituted with 1 or 2 groups represented by R6 or 1 group represented by R6 or 1 group represented by R7, heterocyclyl, wherein the heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring comprising a single heteroatom selected from N, O, and S(O)2, and wherein the heterocyclyl moieties are optionally substituted with 1 group represented by R6 or 1 group represented by R7, heterocyclyl C1-C2alkyl, wherein the heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring comprising 1, 2, or 3 heteroatoms individually selected from N and O, and wherein the heterocyclyl moieties are optionally substituted with a group represented by R6 or 1 group represented by R7; or R4 is a 7- to 9-membered annular ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1-C2 alkylene ligand; or R4 is a 6- to 9-membered non-aromatic spirocyclic carbocyclyl ring system, optionally comprising 1, 2, or 3 heteroatoms individually selected from N and O, optionally substituted with 1 or 2 groups represented by R6, and optionally linked to the rest of the molecule via a C1C2alkylene ligand; R5 is C1-C6 alkyl, hydroxyC1-C4 alkyl, C3-C4 cycloalkyl, C3-C4 cycloalkylC1-C2 alkyl, phenyl, heteroaryl, where heteroaryl is a monocyclic ring Petition 870250055585, dated 01 / 07 / 2025, p. 42 / 501 29 / 236 aromatic 5 or 6 membered comprising 1 or 2 heteroatoms individually selected from N, O and S, heterocyclyl, wherein the heterocyclyl is a non-aromatic bicyclic ring of 9 to 10 membered comprising 1 or 2 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1 or 2, which may be the same or different, selected from R9; R6 is chlorine, fluorine, methyl, difluoromethyl, or trifluoromethyl; R7 is isopropylsulfonyl, cyclopropyl, cyclohexyl, phenyl, benzyl, phenoxy, or pyridyl, wherein each cycloalkyl, phenyl, or pyridyl group is optionally replaced by 1 group represented by R8; R8 is chlorine, fluorine, or trifluoromethyl; and R9 is chlorine, fluorine, or methyl.
[0074] In another set of modalities, A is N or CH; R1 is hydrogen, cyano, or methoxymethylcarbonyl; R2 is hydrogen; R3 is hydroxy, methoxy, ethoxy, isopropoxy, allyloxy, or methoxymethylcarbonyloxy; R4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1,5-dimethylhexyl, 4,4-dimethylpent-2-ynyl, 1methylcyclopropyl, 1-cyclohexylcyclopropyl, 4fluorophenylcyclopropyl, (4-chlorophenyl)methylcylopropyl, 2,2-dimethylcyclobutyl, 4-fluorophenoxycyclobutyl, 1trifluoromethylcyclopropylmethyl, (5-(trifluoromethyl)-2pyridyl)cyclopropylmethyl, (6-chloro-3Petition 870250055585, of 07 / 01 / 2025, page 43 / 501 30 / 236 pyridyl)cyclopropylmethyl, benzyl, phenoxybenzyl, 4-trifluoromethoxyphenylethyl, 2-phenylpropyl, 4-chlorobenzyl, 3,5-difluorobenzyl, 4-fluorophenoxyethyl, 3,5difluorophenoxy-1-methylethyl, 2,4-dichlorophenoxyethyl, benzylimidazol-4-yl, 4-(difluoromethyl)-1-methylpyrazol-3ylmethyl, 3,5-dichloro-4-pyridylmethyl, 1-(5-methyloxazol-2yl)ethyl, 2-trifluoromethylpyrimidin-5-yl, (3,5-dichloro-2pyridyl)-2-ethoxyimino-ethyl, 1-isopropylsulfonyl-4piperidinyl, 1,1-dioxothian-4-yl, 5cyclopropyltetrahydrofuran-3-yl, 3-methyltetrahydrofuran-3ylmethyl, 1-tetrahydropyran-4-ylethyl, 2-methyltriazol-4ylmethyl, 5-(trifluoromethyl)indan-1-yl, 6(trifluoromethyl)indan-1-yl, 1-methylpyrazol[3,4-b]pyridin3-yl, 2,3-dihydrobenzofuran-3-ylmethyl, 2,2-difluoro-1,3benzodioxol-4-ylmethyl, spiro[3,4]octan-3-yl, 8-methyl-5oxaspiro[3.5]nonan-8-yl, 2-oxabicyclo[3.3]heptan-6-yl, 7,7-dimethyl-2-oxabicyclo[3.2.0]heptan-6-yl, 2oxabicyclo[3.2.0]heptan-7-yl or 4-oxaspiro[2,3]heptan-6-yl; e R5 is 2,3-dihydroxypropyl, cyclobutyl, cyclopropylmethyl, phenyl, 3-fluorophenyl, 3-chlorophenyl, 3methylphenyl, 3-methoxyphenyl, 3,5-difluorophenyl, 3,5dichlorophenyl, 3,5-dimethylphenyl, 3,5-dimethoxyphenyl, pyridin-4-yl, 2-fluoropyridin-4-yl, 2-chloropyridin-4-yl, 2,6-difluoropyridin-4-yl, 2,6-dichloropyridin-4-yl, pyridin-3-yl, 6-fluoropyridin-3-yl, 5-fluoropyridin-3-yl, 6-chloropyridin-3-yl, 5-chloropyridin-3-yl, isothiazol4-yl, thiazol-2-yl, pyrimidin-5-yl or 1,3-benzodioxol-5yl.
[0075] In an additional set of modalities, Petition 870250055585, dated 01 / 07 / 2025, page 44 / 501 31 / 236 A is CH; R1 is hydrogen or cyano; R2 is hydrogen; R3 is hydroxy, methoxy, or ethoxy; R4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1methylcyclopropyl, 2,2-dimethylcyclobutyl, or spiro[3.4]octan-3-yl; R5 is C1-C6 alkyl, hydroxyC1-C4 alkyl, C3-C4 cycloalkyl, C3-C4 cycloalkylC1-C2 alkyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, heterocyclyl, wherein heterocyclyl is a 9- to 10-membered non-aromatic bicyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, and in which the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1 or 2, which may be the same or different, selected from R9; and R9 is chlorine, fluorine, or methyl.
[0076] In yet another set of modalities, A is N or CH; R1 is hydrogen, cyano, or methoxymethylcarbonyl; R2 is hydrogen; R3 is hydroxy, methoxy, or ethoxy; R4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1methylcyclopropyl, 2,2-dimethylcyclobutyl, or spiro[3.4]octan-3-yl; and R5 is 3,5-difluorophenyl, 2,6-dichloropyridin-4-yl, or isothiazol-4-yl. Petition 870250055585, dated 01 / 07 / 2025, page 45 / 501 32 / 236
[0077] In a set of embodiments, R4 is C3C4cycloalkyl optionally substituted with 1 or 2 groups represented by R6, or R4 is an 8-membered spirocyclic ring system, and R5 is 3,5-difluorophenyl or 2,6-difluoro-4-pyridyl.
[0078] In a set of modalities, A is CH; R1 is hydrogen; R2 is hydrogen; R3 is hydrogen or methoxy; R4 is C1-Cg-alkyl or C3-C-cycloalkyl, wherein the cycloalkyl portions are optionally replaced by 1 or 2 groups represented by R6, or a group represented by R7; R5 is 3-fluorophenyl, 3,5-difluorophenyl, 3,4,5trifluorophenyl, 2-fluoro-4-pyridyl, or 2,6-difluoro-4-pyridyl; R6 is C1-C4 alkyl; and R7 is cyclobutyl.
[0079] In another set of modalities, A is CH; R1 is hydrogen; R2 is hydrogen; R3 is hydrogen or methoxy; R4 is t-butyl, 1,1,2-trimethylpropyl, 1methylcyclobutyl, 1-ethylcyclobutyl, 1isopropylcyclobutyl, 2,2-dimethylcyclobutyl, 1cyclobutylcyclobutyl or 1-methylcyclopentyl; and R5 is 3-fluorophenyl, 3,5-difluorophenyl, 3,4,5trifluorophenyl, 2-fluoro-4-pyridyl, or 2,6-difluoro-4pyridyl. Petition 870250055585, dated 01 / 07 / 2025, page 46 / 501 33 / 236
[0080] Preferably, the compound according to formula (I) is selected from compounds P-1 to P-193 as shown in Table 3 (below). More preferably, the compound according to formula (I) is selected from 6-[(2,6-difluoro-4-pyridyl)amino]-3-hydroxy-Nespiro[3.4]octan-3-yl-pyridine-2-carboxamide (P-3), 2-(3,5-difluoroanilino)-N-isopentyl-5-methoxy-pyrimidine-4-carboxamide (P-8), 6-anilino-N-(2,2-dimethylcyclobutyl)-3-hydroxy-pyridine-2-carboxamide (P-16), 6-[cyano-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-21), 6-[(2,6-difluoro-4-pyridyl)amino]-3-methoxy-N-(2-phenylpropyl)pyridine-2-carboxamide (P-32), N-(4,4-dimethylpent-2-ynyl)-6(isothiazol-4-ylamino)-3-methoxy-pyridine-2-carboxamide (P34), N-[(4-chlorophenyl)methyl]-6-(isothiazol-4-ylamino)-3methoxy-pyridine-2-carboxamide (P-37), 6-(3,5difluoroanilino)-N-[[4-(difluoromethyl)-1-methyl-pyrazol-3yl]methyl]-3-methoxy-pyridine-2-carboxamide (P-63), 6-(3,5difluoroanilino)-3-metoxi-N-[[1-[5-(trifluorometil)-2piridil]ciclopropil]metil]piridina-2-carboxamida (P-72), N[(2,2-difluoro-1,3-benzodioxol-4-il)metil]-6-(isotiazol-4ilamino)-3-metoxi-piridina-2-carboxamida (P-82), 6(isotiazol-4-ilamino)-3-metoxi-N-[[1(trifluorometil)ciclopropil]metil]piridina-2-carboxamida (P-83), 6-(3,5-difluoroanilino)-N-(2,2-dimetilciclobutil)3-prop-2-inoxi-piridina-2-carboxamida (P-86), 6-(3,5difluoroanilino)-N-(2,2-dimetilciclobutil)-3-isopropoxipiridina-2-carboxamida (P-87), 6-[(2,6-difluoro-4piridil)amino]-3-metoxi-N-(1-metilciclopropil)piridina-2carboxamida (P-92), N-(2,2-dimetilpropil)-6-[(5-fluoro-3, Petição 870250055585, de 01 / 07 / 2025, pág. 47 / 501 34 / 236 pyridyl)amino]-3-methoxy-pyridine-2-carboxamide (P-105), Nterc-butyl-6-(3,5-difluoroanilino)-4-methoxy-pyridine-2-carboxamide (P-116), N-(1-cyanocyclopentyl)-6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-pyridine-2-carboxamide (P-125), 6-(3,5-difluoroanilino)-3-methoxy-N-(3-methyloxetan3-yl)pyridine-2-carboxamide (P-128), 6-(3,5dichloroanilino)-N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-130), 6-(3-chloro-4-methyl-anilino)-N-(2,2dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-132), 6(4-cloro-3,5-difluoro-anilino)-N-(2,2-dimethylpropyl)-3methoxy-pyridine-2-carboxamide (P-135), 6-[(2,6-difluoro-4pyridyl)amino]-N-(1,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-167), N-(1-ciclobutilciclobutil)-6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-pyridina-2-carboxamide (P-182), 6-(3,5-difluoroanilino)-N-(2,2-dimethylciclobutil)3-hydroxy-pyridina-2-carboxamide (P-3), N-(2,2dimethylciclobutil)-6-[(5-fluoro-3-pyridyl)amino]-3-hydroxypyridina-2-carboxamida (P-12), N-(2,2-dimethylcyclobutyl)-3hydroxy-6-(isothiazol-4-ylamino)pyridine-2-carboxamide (P19), 6-(3,5-difluoroanilino)-N-(4,4-dimethylpent-2-ynyl)-3methoxy-pyridine-2-carboxamide (P-28), 6-(isothiazol-4ylamino)-3-methoxy-N-spiro[3.4]octan-3-yl-pyridine-2-carboxamide (P-33), 6-[(2,6-difluoro-4-pyridyl)amino]-N(4,4-dimethylpent-2-ynyl)-3-methoxy-pyridine-2-carboxamide (P-35), N-(1,5-dimethylhexyl)-6-(isothiazol-4-ylamino)-3methoxy-pyridine-2-carboxamide (P-36), N-[2-(3,5difluorophenoxy)-1-methyl-ethyl]-6-(isothiazol-4-ylamino)-3methoxy-pyridine-2-carboxamide (P-38), N-[2-(2,4dichlorophenoxy)ethyl]-6-(isothiazol-4-ylamino)-3-methoxypyridine-2-carboxamide (P-39), 6-(cyclopropylmethylamino)-N, Petition 870250055585, de 01 / 07 / 2025, pág. 48 / 501 35 / 236 (2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamida (P-40), 6-(ciclobutilamino)-N-(2,2-dimethylpropyl)-3-methoxypyridine-2-carboxamida (P-41), N-(2,2-dimethylpropyl)-6(2,2-dimethylpropylamino)-3-methoxy-pyridine-2-carboxamide (P-43), 6-(3,5-difluoroanilino)-3-(difluoromethoxy)-N-(2,2dimethylciclobutil)pyridine-2-carboxamide (P-46), 6-(3,5difluoroanilino)-N-(2,3-di-hidrobenzofuran-3-ylmetil)-3methoxy-pyridine-2-carboxamide (P-60), N-[(3,5-dichloro-4pyridyl)methyl]-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-66), 6-(3,5-difluoroanilino)-3-methoxy-N-[1(5-methyloxazol-2-yl)ethyl]pyridine-2-carboxamide (P-71), N[[1-(6-chloro-3-pyridyl)cyclopropyl]methyl]-6-(3,5difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-73),N[2-(3,5-dichloro-2-pyridyl)-2-ethoxyimino-ethyl]-6-(3,5difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-75),Ntert-butyl-6-(3,5-difluoroanilino)-3-prop-2-ynoxy-pyridine2-carboxamide (P-96), 6-(3,5-difluoroanilino)-N-(2,2dimethylpropyl)pyridine-2-carboxamide (P-111),N-(1cyanocyclobutyl)-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-129), N-(2,2-dimethylpropyl)-6-(4fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-133), N(2,2-dimethylpropyl)-3-methoxy-6-(3-methylanilino)pyridine-2-carboxamide (P-140), 6-(4-chloro-3-fluoro-anilino)-N-(2,2dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-144), Ntert-butyl-6-(3-chloro-4-methyl-anilino)-3-methoxy-pyridine-2-carboxamide (P-151), 6-(benzofuran-5-ylamino)-N-tert-butyl3-methoxy-pyridine-2-carboxamide (P-157), 6-(3,5difluoroanilino)-N-(2,2-dimethylciclobutil)-3-metilpiridana-2-carboxamida (P-175), N-(3,5-difluorofenil)-N-[6[(2,2-dimethylciclobutil)carbamoyl]-5-methoxy-2Petição 870250055585, de 01 / 07 / 2025, pág. 49 / 501, 36 / 236 pyridyl]carbamate de methyla (P-191), 6-[(2,6-difluoro-4pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-3-hydroxypyridine-2-carboxamide (P-1), 6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-N-spiro[3.4]octan-3-yl-pyridine-2-carboxamide (P-6), 2-[(2,6-difluoro-4-pyridyl)amino]-Nisopentyl-5-methoxy-pyrimidine-4-carboxamide (P-9), 2-(3,5difluoroanilino)-N-(2,2-dimethylcyclobutyl)-5-methoxypyrimidine-4-carboxamide (P-10), 6-(N-cyano-3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-20), 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-22), 6(3,5-difluoroanilino)-3-methoxy-N-(2-phenylpropyl)pyridine-2-carboxamide (P-23), N-benzyl-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-25), 6-(3,5-difluoroanilino)-N-[(3,5-difluorophenyl)methyl]-3-methoxypyridine-2-carboxamide (P-26), 6-(3,5-difluoroanilino)-N[2-(4-fluorophenoxy)ethyl]-3-methoxy-pyridine-2-carboxamide (P-27), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2dimethylpropyl)-3-methoxy-pyridine-2-carboxamida (P-30), 6(3,5-difluoroanilino)-N-(2,2-dimethylciclobutil)-3-ethoxipyridina-2-carboxamida (P-44), 6-(3,5-difluoroanilino)-N[2-(4-fluorophenoxy)ciclobutil]-3-methoxy-pyridine-2-carboxamide (P-45), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-[5-(trifluorometil)indan-1-yl]pyridine-2carboxamide (P-47), 6-(3,5-difluoroanilino)-3-methoxy-N-[5(trifluorometil)indan-1-yl]pyridine-2-carboxamide (P-55), 6-(3,5-difluoroanilino)-3-methoxy-N-[6(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-56), 6-(3,5-difluoroanilino)-3-methoxy-N-[(4-phenoxyphenyl)methyl]pyridine-2-carboxamide (P-57), 6-(3,5 Petition 870250055585, de 01 / 07 / 2025, pág. 50 / 501 37 / 236 difluoroanilino)-N-[(2,2-difluoro-1,3-benzodioxol-4yl)metil]-3-methoxy-pyridine-2-carboxamide (P-58), 6-(3,5difluoroanilino)-3-methoxy-N-(2-oxabiciclo[3.2.0]heptan-7yl)pyridine-2-carboxamide (P-59), 6-(3,5-difluoroanilino)3-methoxy-N-[[1-(trifluorometil)ciclopropyl]metil]pyridina2-carboxamide (P-62), N-(5-ciclopropyltetra-hidrofuran-3yl)-6-(3,5-difluoroanilino)-3-methoxy-pyridina-2-carboxamide (P-65), 6-(3,5-difluoroanilino)-3-methoxy-N-[(8-methyl-5oxaespiro[3.5]nonan-8-yl)methyl]pyridine-2-carboxamide (P67), 6-(3,5-difluoroanilino)-3-methoxy-N-[(3-methyltetrahydrofuran-3-yl)methyl]pyridine-2-carboxamide (P-68), 6(3,5-difluoroanilino)-3-methoxy-N-(4-oxaespiro[2.4]heptan-6yl)pyridine-2-carboxamide (P-70), 6-(3,5-difluoroanilino)3-methoxy-N-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine-2-carboxamide (P-74), 6-(3,5-difluoroanilino)-N-(7,7-dimethyl2-oxabicyclo[3.2.0]heptan-6-yl)-3-methoxy-pyridine-2-carboxamide (P-76), 6-(isothiazol-4-ylamino)-3-methoxy-N-[5(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-79),. N-tert-butyl-6-(3,5-difluoroanilino)-3-ethoxy-pyridine-2-carboxamide (P-94), 6-[(2,6-difluoro-4-pyridyl)amino]-N(1,5-dimethyl-hexyl)-3-methoxy-pyridine-2-carboxamide (P102), N-(2,2-dimethylciclobutil)-6-[(5-fluoro-3pyridyl)amino]-3-methoxy-pyridine-2-carboxamide (P-104), 6(3,5-difluoroanilino)-3-methoxy-N-(1-metilciclohexyl)pyridine-2-carboxamide (P-108), 6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-N-(1-metilcyclopentyl)pyridine-2carboxamide (P-109), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1-metilciclo-hexyl)pyridina-2-carboxamida (P110), N-tert-butil-6-(3,5-difluoroanilino)pyridina-2carboxamida (P-112), 6-[(2,6-difluoro-4-pyridyl)amino]-N Petition 870250055585, de 01 / 07 / 2025, pág. 51 / 501 38 / 236 (2,2-dimethylpropyl)pyridine-2-carboxamide (P-113), N-tertbutyl-6-[(2,6-difluoro-4-pyridyl)amino]pyridine-2carboxamide (P-114), N-[[3,5bis(trifluoromethyl)phenyl]methyl]-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-115), N-tert-butyl-6-(3,5difluoroanilino)-3-methoxy-1-oxido-pyridin-1-ium-2carboxamide (P-117), 6-(3,5-difluoroanilino)-N-(1methylcyclopentyl)pyridine-2-carboxamide (P-119), N-(3cyanothietan-3-yl)-6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxamide (P-121), 6-(3,5-difluoroanilino)-3methoxy-N-(3-methyltetra-hydrofuran-3-yl)pyridine-2-carboxamide (P-122), N-(1-cyanocyclopentyl)-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-123), 6-(3-chloro-5-fluoro-anilino)-N-(2,2-dimethylpropyl)-3methoxy-pyridine-2-carboxamide (P-134), N-(2,2dimethylpropyl)-6-(3-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-139), N-(2,2-dimethylpropyl)-3-methoxy-6(3,4,5-trifluoroanilino)pyridine-2-carboxamide (P-145), Ntert-butyl-6-(3-cyanoanilino)-3-methoxy-pyridine-2-carboxamide (P-146), N-tert-butyl-6-(3-cyano-5-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-147), N-tert-butyl-6-(3,5-dichloroanilino)-3-methoxy-pyridine-2-carboxamide (P-148), N-tert-butyl-6-(3-chloro-5-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-152), N-tert-butyl-6-(4-chloro-3,5-difluoro-anilino)-3-methoxy-pyridine-2-carboxamide (P-153), N-tert-butyl-6-(3-chloroanilino)-3methoxy-pyridine-2-carboxamide (P-155), 6-(3,5difluoroanilino)-N-(1,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-168), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1,2,2-trimethylpropyl)pyridine-2-carboxamide (Petition 870250055585, dated 01 / 07 / 2025, pág. 52 / 501 39 / 236 169), 6-(3,5-difluoroanilino)-3-methoxy-N-(1,2,2trimethylpropyl)pyridine-2-carboxamide (P-170), 6-(3,5-difluoroanilino)-3-methoxy-N-(1,1,2,2tetramethylpropyl)pyridine-2-carboxamide (P-171), 6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-N-(1,1,2trimethylpropyl)pyridine-2-carboxamide (P-173), 6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-N-(1,1,2,2tetramethylpropyl)pyridine-2-carboxamide (P-174), N-[1-(6chloro-2-pyridyl)cyclobutyl]-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-177), 6-[(2,6-difluoro-4pyridyl)amino]-N-(1-isopropylcyclobutyl)-3-methoxy-pyridine2-carboxamide (P-181), N-[3-(4-chlorophenyl)cyclobutyl]-6(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P187), 6-(N-acetyl-3,5-difluoro-anilino)-N-(2,2dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-189), N-tert-butyl-6-(2-chloro-3,5-difluoro-anilino)-3-methoxypyridine-2-carboxamide (P-190), 6-[(2,6-difluoro-4pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine2-carboxamide (P-4), 6-(3,5-difluoroanilino)-N-(2,2dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-7), N-tert-butyl-6-[(2,6-difluoro-4-pyridyl)amino]-3-methoxypyridine-2-carboxamide (P-91), N-tert-butyl-6-(3,5difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-93), 6(3,5-difluoroanilino)-3-methoxy-N-(1methylcyclopentyl)pyridine-2-carboxamide (P-107), 6-(3,5difluoroanilino)-3-methoxy-N-(1-methylcyclobutyl)pyridine-2carboxamide (P-118), 6-[(2,6-difluoro-4-pyridyl)amino]-N(1-methylcyclopentyl)pyridine-2-carboxamide (P-120), 6[(2,6-difluoro-4-pyridyl)amino]-3-methoxy-N-(1methylcyclobutyl)pyridine-2-carboxamide (P-127), N-tert Petition 870250055585, dated 01 / 07 / 2025, page 53 / 501 40 / 236 butil-6-[(2-fluoro-4-piridil)amino]-3-metoxi-piridina-2carboxamida (P-156), N-terc-butil-6-(3-fluoroanilino)-3metoxi-piridina-2-carboxamida (P-160), N-terc-butil-3metoxi-6-(3,4,5-trifluoroanilino)piridina-2-carboxamida (P162), 6-(3,5-difluoroanilino)-3-metoxi-N-(1,1,2trimetilpropil)piridina-2-carboxamida (P-172), N-(1ciclobutilciclobutil)-6-(3,5-difluoroanilino)-3-metoxipiridina-2-carboxamida (P-176), 6-(3,5-difluoroanilino)-N(1-etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-178), 6-(3,5-difluoroanilino)-N-(1-isopropilciclobutil)-3-metoxipiridina-2-carboxamida (P-179), N-(1-terc-butilciclobutil)6-(3,5-difluoroanilino)-3-metoxi-piridina-2-carboxamida (P180), 6-[(2,6-difluoro-4-piridil)amino]-N-(1etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-183), e N-(1-terc-butilciclobutil)-6-[(2,6-difluoro-4piridil)amino]-3-metoxi-piridina-2-carboxamida (P-185).
[0081] Even more preferably, the compound according to formula (I) is selected from 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-hydroxypyridine-2-carboxamide (P-3), N-(2,2-dimethylcyclobutyl)-6-[(5-fluoro-3-pyridyl)amino]-3-hydroxypyridine-2-carboxamide (P-12), N-(2,2-dimethylcyclobutyl)-3-hydroxy-6-(isothiazol-4-ylamino)pyridine-2-carboxamide (P-19), 6-(3,5-difluoroanilino)-N-(4,4-dimethylpent-2-ynyl)-3-methoxypyridine-2-carboxamide (P-28), 6-(isothiazol-4-ylamino)-3-methoxy-N-spiro[3.4]octan-3-yl-pyridine-2-carboxamide (P33) N-[2-(3,5-difluorophenoxy)-1-methyl Petition 870250055585, dated 01 / 07 / 2025, page 54 / 501 41 / 236 ethyl]-6-(isothiazol-4-ylamino)-3-methoxy-pyridine-2-carboxamide (P-38), N-[2-(2,4-dichlorofenoxi)ethyl]-6(isothiazol-4-ylamino)-3-methoxy-pyridine-2-carboxamide (P39), 6-(ciclopropylmetilamino)-N-(2,2-dimethylpropyl)-3methoxy-pyridine-2-carboxamida (P-40), 6-(ciclobutilamino)N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamida (P41), N-(2,2-dimethylpropyl)-6-(2,2-dimethylpropyl)-3methoxy-pyridine-2-carboxamide (P-43), 6-(3,5difluoroanilino)-3-(difluoromethoxy)-N-(2,2dimethylciclobutil)pyridine-2-carboxamide (P-46), 6-(3,5-difluoroanilino)-N-(2,3-dihydrobenzofuran-3-ylmethyl)-3methoxy-pyridine-2-carboxamide (P-60), N-[(3,5-dichloro-4pyridyl)methyl]-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-66), 6-(3,5-difluoroanilino)-3-methoxy-N-[1(5-methyloxazol-2-yl)ethyl]pyridine-2-carboxamide (P-71), N[[1-(6-chloro-3-pyridyl)cyclopropyl]methyl]-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-73), N[2-(3,5-dichloro-2-pyridyl)-2-ethoxyimino-ethyl]-6-(3,5difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-75),Ntert-butyl-6-(3,5-difluoroanilino)-3-prop-2-ynoxy-pyridine2-carboxamide (P-96), 6-(3,5-difluoroanilino)-N-(2,2dimethylpropyl)pyridine-2-carboxamide (P-111),N-(1cyanocyclobutyl)-6-(3,5-difluoroanilino)-3-methoxy-pyridine2-carboxamide (P-129), N-(2,2-dimethylpropyl)-6-(4fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-133), N(2,2-dimethylpropyl)-3-methoxy-6-(3-methylanilino)pyridine-2-carboxamide (P-140), 6-(4-cloro-3-fluoro-anilino)-N-(2,2dimethylpropyl)-3-methoxy-pyridina-2-carboxamida (P-144), Nterc-butil-6-(3-cloro-4-metil-anilino)-3-methoxy-pyridina-2carboxamida (P-151), 6-(benzofuran-5-ylamino)-N-tert-butilPetição 870250055585, de 01 / 07 / 2025, pág. 55 / 501, 42 / 236 3-methoxy-pyridina-2-carboxamida (P-157), 6-(3,5difluoroanilino)-N-(2,2-dimethylciclobutil)-3-metilpiridina-2-carboxamida (P-175), N-(3,5-difluorofenil)-N-[6[(2,2-dimethylciclobutil)carbamoyl]-5-methoxy-2pyridyl]carbamato de metil (P-191), 6-[(2,6-difluoro-4pyridyl)amino]-N-(2,2-dimethylciclobutil)-3-hidroxipiridina-2-carboxamide (P-1), 6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-N-espiro[3.4]octan-3-yl-pyridin-2-carboxamide (P-6), 2-[(2,6-difluoro-4-pyridyl)amino]-Nisopentyl-5-methoxy-pyrimidine-4-carboxamide (P-9), 2-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-5-methoxypyrimidine-4-carboxamide (P-10), 6-(N-cyano-3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-20), 6-(3,5-difluoroanilino)-N-(2,2dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-22), 6(3,5-difluoroanilino)-3-methoxy-N-(2-phenylpropyl)pyridine-2-carboxamide (P-23), N-benzyl-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-25), 6-(3,5difluoroanilino)-N-[(3,5-difluorophenyl)methyl]-3-methoxypyridine-2-carboxamide (P-26), 6-(3,5-difluoroanilino)-N[2-(4-fluorophenoxy)ethyl]-3-methoxypyridine-2-carboxamide (P-27), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2dimethylpropyl)-3-methoxypyridine-2-carboxamide (P-30), 6(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-ethoxypyridine-2-carboxamide (P-44), 6-(3,5-difluoroanilino)-N[2-(4-fluorophenoxy)cyclobutyl]-3-methoxypyridine-2-carboxamide (P-45), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-[5-(trifluorometil)indan-1-yl]pyridine-2carboxamide (P-47), 6-(3,5-difluoroanilino)-3-methoxy-N-[5(trifluorometil)indan-1-yl]pyridine-2-carboxamide (P-55), Petition 870250055585, de 01 / 07 / 2025, pág. 56 / 501 43 / 236 6-(3,5-difluoroanilino)-3-methoxy-N-[6(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-56), 6-(3,5-difluoroanilino)-3-methoxy-N-[(4phenoxyphenyl)methyl]pyridine-2-carboxamide (P-57), 6-(3,5-difluoroanilino)-N-[(2,2-difluoro-1,3-benzodioxol-4yl)methyl]-3-methoxy-pyridine-2-carboxamide (P-58), 6-(3,5-difluoroanilino)-3-methoxy-N-(2-oxabicyclo[3.2.0]heptan-7yl)pyridine-2-carboxamide (P-59), 6-(3,5-difluoroanilino)3-methoxy-N-[[1-(trifluoromethyl)cyclopropyl]methyl]pyridine2-carboxamide (P-62), N-(5-cyclopropyltetra-hydrofuran-3yl)-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-65), 6-(3,5-difluoroanilino)-3-methoxy-N-[(8-methyl-5oxaespiro[3.5]nonan-8-yl)methyl]pyridine-2-carboxamide (P67), 6-(3,5-difluoroanilino)-3-methoxy-N-[(3-methyltetrahydrofuran-3-yl)methyl]pyridine-2-carboxamide (P-68), 6(3,5-difluoroanilino)-3-methoxy-N-(4-oxaespiro[2.4]heptan-6yl)pyridine-2-carboxamide (P-70), 6-(3,5-difluoroanilino)3-methoxy-N-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine-2-carboxamide (P-74), 6-(3,5-difluoroanilino)-N-(7,7-dimethyl2-oxabicyclo[3.2.0]heptan-6-yl)-3-methoxy-pyridine-2-carboxamide (P-76), 6-(isothiazol-4-ylamino)-3-methoxy-N-[5(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-79),. N-tert-butyl-6-(3,5-difluoroanilino)-3-ethoxy-pyridine-2-carboxamide (P-94), 6-[(2,6-difluoro-4-pyridyl)amino]-N(1,5-dimethyl-hexyl)-3-methoxy-pyridine-2-carboxamide (P102), N-(2,2-dimethylcyclobutyl)-6-[(5-fluoro-3pyridyl)amino]-3-methoxy-pyridine-2-carboxamide (P-104), 6(3,5-difluoroanilino)-3-methoxy-N-(1-methylcyclohexyl)pyridine-2-carboxamide (P-108), 6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-N-(1-methylcyclopentyl)pyridine-2Petition 870250055585, of 01 / 07 / 2025, pág. 57 / 501 44 / 236 carboxamide (P-109), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1-methylcyclohexyl)pyridine-2-carboxamide (P110), N-tert-butyl-6-(3,5-difluoroanilino)pyridine-2-carboxamide (P-112), 6-[(2,6-difluoro-4-pyridyl)amino]-N(2,2-dimethylpropyl)pyridine-2-carboxamide (P-113), N-tert-butyl-6-[(2,6-difluoro-4-pyridyl)amino]pyridine-2-carboxamide (P-114), N-[[3,5bis(trifluoromethyl)phenyl]methyl]-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-115), N-tert-butyl-6-(3,5difluoroanilino)-3-methoxy-1-oxido-pyridin-1-ium-2carboxamide (P-117), 6-(3,5-difluoroanilino)-N-(1methylcyclopentyl)pyridine-2-carboxamide (P-119), N-(3cyanothietan-3-yl)-6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxamide (P-121), 6-(3,5-difluoroanilino)-3methoxy-N-(3-methyltetra-hydrofuran-3-yl)pyridine-2carboxamide (P-122), N-(1-cyanocyclopentyl)-6-(3,5difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-123), 6-(3-chloro-5-fluoro-anilino)-N-(2,2-dimethylpropyl)-3methoxy-pyridine-2-carboxamide (P-134), N-(2,2dimethylpropyl)-6-(3-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-139), N-(2,2-dimethylpropyl)-3-methoxy-6(3,4,5-trifluoroanilino)pyridine-2-carboxamide (P-145), Ntert-butyl-6-(3-cyanoanilino)-3-methoxy-pyridine-2-carboxamide (P-146), N-tert-butyl-6-(3-cyano-5-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-147), N-tert-butyl-6-(3,5-dichloroanilino)-3-methoxy-pyridine-2-carboxamide (P-148), N-tert-butil-6-(3-cloro-5-fluoroanilino)-3-methoxy-pyridina-2-carboxamida (P-152), N-tercbutil-6-(4-cloro-3,5-difluoro-anilino)-3-methoxy-pyridina-2carboxamida (P-153), N-tert-butil-6-(3-chloro-3,5-difluoro-anilino)-3-methoxy-pyridine-2-carboxamida (P-153) Petition 870250055585, de 01 / 07 / 2025, pág. 58 / 501 45 / 236 methoxy-pyridine-2-carboxamide (P-155), 6-(3,5-difluoroanilino)-N-(1,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-168), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1,2,2-trimethylpropyl)pyridine-2-carboxamide (P169), 6-(3,5-difluoroanilino)-3-methoxy-N-(1,2,2trimethylpropyl)pyridine-2-carboxamide (P-170), 6-(3,5-difluoroanilino)-3-methoxy-N-(1,1,2,2tetramethylpropyl)pyridine-2-carboxamide (P-171), 6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-N-(1,1,2trimethylpropyl)pyridine-2-carboxamide (P-173), 6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-N-(1,1,2,2tetramethylpropyl)pyridine-2-carboxamide (P-174), N-[1-(6chloro-2-pyridyl)cyclobutyl]-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-177), 6-[(2,6-difluoro-4pyridyl)amino]-N-(1-isopropylcyclobutyl)-3-methoxy-pyridine2-carboxamide (P-181), N-[3-(4-chlorophenyl)cyclobutyl]-6(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P187), 6-(N-acetyl-3,5-difluoro-anilino)-N-(2,2dimethylciclobutil)-3-methoxy-pyridine-2-carboxamide (P-189),N-tert-butil-6-(2-cloro-3,5-difluoro-anilino)-3-methoxypyridina-2-carboxamide (P-190), 6-[(2,6-difluoro-4pyridyl)amino]-N-(2,2-dimethylciclobutil)-3-methoxy-pyridina2-carboxamide (P-4), 6-(3,5-difluoroanilino)-N-(2,2dimethylciclobutil)-3-methoxy-pyridine-2-carboxamide (P-7), N-tert-butyl-6-[(2,6-difluoro-4-pyridyl)amino]-3-methoxypyridine-2-carboxamide (P-91), N-tert-butyl-6-(3,5difluoroanilino)-3-methoxypyridine-2-carboxamide (P-93), 6(3,5-difluoroanilino)-3-methoxy-N-(1methylcyclopentyl)pyridine-2-carboxamide (P-107), 6-(3,5difluoroanilino)-3-methoxy-N-(1-methylcyclobutyl)pyridine-2 Petition 870250055585, de 01 / 07 / 2025, pág. 59 / 501 46 / 236 carboxamida (P-118), 6-[(2,6-difluoro-4-piridil)amino]-N(1-metilciclopentil)piridina-2-carboxamida (P-120), 6[(2,6-difluoro-4-piridil)amino]-3-metoxi-N- (1metilciclobutil)piridina-2-carboxamida (P-127), N-tercbutil-6-[(2-fluoro-4-piridil)amino]-3-metoxi-piridina-2carboxamida (P-156), N-terc-butil-6-(3-fluoroanilino)-3metoxi-piridina-2-carboxamida (P-160), N-terc-butil-3metoxi-6-(3,4,5-trifluoroanilino)piridina-2-carboxamida (P162), 6-(3,5-difluoroanilino)-3-metoxi-N-(1,1,2trimetilpropil)piridina-2-carboxamida (P-172), N-(1ciclobutilciclobutil)-6-(3,5-difluoroanilino)-3-metoxipiridina-2-carboxamida (P-176), 6-(3,5-difluoroanilino)-N(1-etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-178), 6-(3,5-difluoroanilino)-N-(1-isopropilciclobutil)-3-metoxipiridina-2-carboxamida (P-179), N-(1-terc-butilciclobutil)6-(3,5-difluoroanilino)-3-metoxi-piridina-2-carboxamida (P180), 6-[(2,6-difluoro-4-piridil)amino]-N-(1etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-183),and N-(1-tert-butylcyclobutyl)-6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-pyridine-2-carboxamide (P-185).
[0082] Even more preferably, the compound according to formula (I) is selected from 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-hydroxypyridine-2-carboxamide (P-3), N-(2,2-dimethylcyclobutyl)-6-[(5-fluoro-3-pyridyl)amino]-3-hydroxypyridine-2-carboxamide (P-12), N-(2,2-dimethylcyclobutyl)-3-hydroxy-6-(isothiazol-4-ylamino)pyridine-2-carboxamide (P-19), 6-(3,5-difluoroanilino)-N-(4,4-dimethylpent-2-ynyl)-3-methoxypyridine-2-carboxamide (P-28), 6-(isothiazol-4-ylamino)-3-methoxy-N-spiro[3.4]octan-3-yl-pyridine-2-carboxamide (Petition 870250055585, of 01 / 07 / 2025, page 60 / 501) 47 / 236 33), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(4,4-dimethylpent2-ynyl)-3-methoxy-pyridine-2-carboxamide (P-35), N-(1,5dimethyl-hexyl)-6-(isothiazol-4-ylamino)-3-methoxy-pyridine-2-carboxamide (P-36), N-[2-(3,5-difluorophenoxy)-1-methylethyl]-6-(isothiazol-4-ylamino)-3-methoxy-pyridine-2-carboxamide (P-38), N-[2-(2,4-dichlorophenoxy)ethyl]-6(isothiazol-4-ylamino)-3-methoxy-pyridine-2-carboxamide (P39), 6-(cyclopropylmethylamino)-N-(2,2-dimethylpropyl)-3methoxy-pyridine-2-carboxamide (P-40), 6-(ciclobutilamino)N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamida (P41), N-(2,2-dimethylpropyl)-6-(2,2-dimethylpropylamino)-3methoxy-pyridine-2-carboxamida (P-43), 6-(3,5difluoroanilino)-3-(difluoromethoxy)-N-(2,2-dimethylpropyl)pyridine-2-carboxamide (P-46), 6-(3,5difluoroanilino)-N-(2,3-di-hidrobenzofuran-3-ilmetil)-3methoxy-pyridina-2-carboxamida (P-60), N-[(3,5-dichloro-4piridil)metil]-6-(3,5-difluoroanilino)-3-methoxy-pyridina-2carboxamida (P-66),5-difluoroanilino)-3-methoxy-N-[1(5-methyloxazol-2-yl)ethyl]pyridine-2-carboxamide (P-71), N[[1-(6-chloro-3-pyridyl)cyclopropyl]methyl]-6-(3,5difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-73), N[2-(3,5-dichloro-2-pyridyl)-2-ethoxyimino-ethyl]-6-(3,5difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-75), Ntert-butyl-6-(3,5-difluoroanilino)-3-prop-2-ynoxy-pyridine2-carboxamide (P-96), 6-(3,5-difluoroanilino)-N-(2,2dimethylpropyl)pyridine-2-carboxamide (P-111), N-(1cyanocyclobutyl)-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-129), N-(2,2-dimethylpropyl)-6-(4fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-133), N(2,2-dimethylpropyl)-3-methoxy-6-(3-methylanilino)pyridine-2, Petition 870250055585, de 01 / 07 / 2025, pág. 61 / 501 48 / 236 carboxamide (P-140), 6-(4-chloro-3-fluoro-anilino)-N-(2,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-144), Ntert-butyl-6-(3-chloro-4-methyl-anilino)-3-methoxy-pyridine-2-carboxamide (P-151), 6-(benzofuran-5-ylamino)-N-tert-butyl3-methoxy-pyridine-2-carboxamide (P-157), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methylpyridine-2-carboxamide (P-175), N-(3,5-difluorophenyl)-N-[6[(2,2-dimethylcyclobutyl)carbamoyl]-5-methoxy-2pyridyl]carbamate methyl (P-191), 6-[(2,6-difluoro-4pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-3-hydroxypyridine-2-carboxamide (P-1), 6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-N-spiro[3.4]octan-3-yl-pyridine-2-carboxamide (P-6), 2-[(2,6-difluoro-4-pyridyl)amino]-Nisopentyl-5-methoxy-pyrimidine-4-carboxamide (P-9), 2-(3,5difluoroanilino)-N-(2,2-dimethylcyclobutyl)-5-methoxypyrimidine-4-carboxamide (P-10), 6-(N-cyano-3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-20), 6-(3,5-difluoroanilino)-N-(2,2dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-22), 6(3,5-difluoroanilino)-3-methoxy-N-(2-phenylpropyl)pyridine-2-carboxamide (P-23), N-benzyl-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-25), 6-(3,5difluoroanilino)-N-[(3,5-difluorophenyl)methyl]-3-methoxypyridine-2-carboxamide (P-26), 6-(3,5-difluoroanilino)-N[2-(4-fluorophenoxy)ethyl]-3-methoxy-pyridine-2-carboxamide (P-27), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-30), 6(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-ethoxypyridine-2-carboxamide (P-44), 6-(3,5-difluoroanilino)-N[2-(4-fluorophenoxy)cyclobutyl]-3-methoxy-pyridine-2. Petition 870250055585, de 01 / 07 / 2025, p. 62 / 501 49 / 236 carboxamide (P-45), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-[5-(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-47), 6-(3,5-difluoroanilino)-3-methoxy-N-[5(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-55), 6-(3,5-difluoroanilino)-3-methoxy-N-[6(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-56), 6-(3,5-difluoroanilino)-3-methoxy-N-[(4phenoxyphenyl)methyl]pyridine-2-carboxamide (P-57), 6-(3,5-difluoroanilino)-N-[(2,2-difluoro-1,3-benzodioxol-4yl)methyl]-3-methoxy-pyridine-2-carboxamide (P-58), 6-(3,5-difluoroanilino)-3-methoxy-N-(2-oxabicyclo[3.2.0]heptan-7yl)pyridine-2-carboxamide (P-59), 6-(3,5-difluoroanilino)3-methoxy-N-[[1-(trifluoromethyl)cyclopropyl]methyl]pyridine2-carboxamide (P-62), N-(5-cyclopropyltetra-hydrofuran-3yl)-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-65), 6-(3,5-difluoroanilino)-3-methoxy-N-[(8-methyl-5oxaespiro[3.5]nonan-8-yl)methyl]pyridine-2-carboxamide (P67), 6-(3,5-difluoroanilino)-3-methoxy-N-[(3-methyltetrahydrofuran-3-yl)methyl]pyridine-2-carboxamide (P-68), 6(3,5-difluoroanilino)-3-methoxy-N-(4-oxaespiro[2.4]heptan-6yl)pyridine-2-carboxamide (P-70), 6-(3,5-difluoroanilino)3-methoxy-N-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine-2-carboxamide (P-74), 6-(3,5-difluoroanilino)-N-(7,7-dimethyl2-oxabicyclo[3.2.0]heptan-6-yl)-3-methoxy-pyridine-2-carboxamide (P-76), 6-(isothiazol-4-ylamino)-3-methoxy-N-[5(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-79),. N-tert-butil-6-(3,5-difluoroanilino)-3-ethoxi-pyridina-2carboxamida (P-94), 6-[(2,6-difluoro-4-pyridyl)amino]-N(1,5-dimethyl-hexyl)-3-methoxy-pyridina-2-carboxamida (P102), N-(2,2-dimethylciclobutil)-6-[(5-fluoro-3)Petição 870250055585, de 01 / 07 / 2025, pág. 63 / 501 50 / 236 pyridyl)amino]-3-methoxy-pyridine-2-carboxamide (P-104), 6(3,5-difluoroanilino)-3-methoxy-N-(1-methylcyclohexyl)pyridine-2-carboxamide (P-108), 6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-N-(1-methylcyclopentyl)pyridine-2-carboxamide (P-109), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1-methylcyclohexyl)pyridine-2-carboxamide (P110), N-tert-butyl-6-(3,5-difluoroanilino)pyridine-2-carboxamide (P-112), 6-[(2,6-difluoro-4-pyridyl)amino]-N(2,2-dimethylpropyl)pyridine-2-carboxamide (P-113), N-tertbutyl-6-[(2,6-difluoro-4-pyridyl)amino]pyridine-2carboxamide (P-114), N-[[3,5bis(trifluoromethyl)phenyl]methyl]-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-115), N-tert-butyl-6-(3,5difluoroanilino)-3-methoxy-1-oxido-pyridin-1-ium-2carboxamide (P-117), 6-(3,5-difluoroanilino)-N-(1methylcyclopentyl)pyridine-2-carboxamide (P-119), N-(3cyanothietan-3-yl)-6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxamide (P-121), 6-(3,5-difluoroanilino)-3methoxy-N-(3-metiltetra-hidrofuran-3-yl)pyridina-2carboxamide (P-122), N-(1-cyanocyclopentyl)-6-(3,5difluoroanilino)-3-methoxy-pyridina-2-carboxamide (P-123), 6-(3-chloro-5-fluoro-anilino)-N-(2,2-dimethylpropyl)-3methoxy-pyridine-2-carboxamide (P-134), N-(2,2dimethylpropyl)-6-(3-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-139), N-(2,2-dimethylpropyl)-3-methoxy-6(3,4,5-trifluoroanilino)pyridine-2-carboxamide (P-145), Ntert-butyl-6-(3-cyanoanilino)-3-methoxy-pyridine-2-carboxamide (P-146), N-tert-butyl-6-(3-cyano-5-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-147), N-tertbutyl-6-(3,5-dichloroanilino)-3-methoxy-pyridine-2Petição 870250055585, of 01 / 07 / 2025, page 64 / 501 51 / 236 carboxamide (P-148), N-tert-butyl-6-(3-chloro-5-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-152), N-tert-butyl-6-(4-chloro-3,5-difluoro-anilino)-3-methoxy-pyridine-2-carboxamide (P-153), N-tert-butyl-6-(3-chloroanilino)-3methoxy-pyridine-2-carboxamide (P-155), 6-(3,5difluoroanilino)-N-(1,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-168), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1,2,2-trimethylpropyl)pyridine-2-carboxamide (P169), 6-(3,5-difluoroanilino)-3-methoxy-N-(1,2,2trimethylpropyl)pyridine-2-carboxamide (P-170), 6-(3,5-difluoroanilino)-3-methoxy-N-(1,1,2,2tetramethylpropyl)pyridine-2-carboxamide (P-171), 6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-N-(1,1,2trimethylpropyl)pyridine-2-carboxamide (P-173), 6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-N-(1,1,2,2tetramethylpropyl)pyridine-2-carboxamide (P-174), N-[1-(6chloro-2-pyridyl)cyclobutyl]-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-177), 6-[(2,6-difluoro-4pyridyl)amino]-N-(1-isopropylcyclobutyl)-3-methoxy-pyridine2-carboxamide (P-181), N-[3-(4-chlorophenyl)cyclobutyl]-6(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P187), 6-(N-acetyl-3,5-difluoro-anilino)-N-(2,2dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-189), N-tert-butyl-6-(2-chloro-3,5-difluoro-anilino)-3-methoxypyridine-2-carboxamide (P-190), 6-[(2,6-difluoro-4pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine2-carboxamide (P-4), 6-(3,5-difluoroanilino)-N-(2,2dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-7), N-tert-butyl-6-[(2,6-difluoro-4-pyridyl)amino]-3-methoxypyridine-2-carboxamide (P-91), N-tert-butyl-6-(3,5Petition 870250055585, dated 01 / 07 / 2025, p. 65 / 501 52 / 236 difluoroanilino)-3-metoxi-piridina-2-carboxamida (P-93), 6(3,5-difluoroanilino)-3-metoxi-N-(1metilciclopentil)piridina-2-carboxamida (P-107), 6-(3,5difluoroanilino)-3-metoxi-N-(1-metilciclobutil)piridina-2carboxamida (P-118), 6-[(2,6-difluoro-4-piridil)amino]-N(1-metilciclopentil)piridina-2-carboxamida (P-120), 6[(2,6-difluoro-4-piridil)amino]-3-metoxi-N-(1metilciclobutil)piridina-2-carboxamida (P-127), N-tercbutil-6-[(2-fluoro-4-piridil)amino]-3-metoxi-piridina-2carboxamida (P-156), N-terc-butil-6-(3-fluoroanilino)-3metoxi-piridina-2-carboxamida (P-160), N-terc-butil-3metoxi-6-(3,4,5-trifluoroanilino)piridina-2-carboxamida (P162), 6-(3,5-difluoroanilino)-3-metoxi-N-(1,1,2trimetilpropil)piridina-2-carboxamida (P-172), N-(1ciclobutilciclobutil)-6-(3,5-difluoroanilino)-3-metoxipiridina-2-carboxamida (P-176), 6-(3,5-difluoroanilino)-N(1-etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-178), 6-(3,5-difluoroanilino)-N-(1-isopropilciclobutil)-3-metoxipiridina-2-carboxamida (P-179),N-(1-tert-butylcyclobutyl)6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P180), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(1ethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-183), and N-(1-tert-butylcyclobutyl)-6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-pyridine-2-carboxamide (P-185).
[0083] More preferably still, the compound according to formula (I) is selected from 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)3-hydroxy-pyridine-2-carboxamide (P-1), 6-[(2,6-difluoro-4-pyridyl)amino]-3-methoxy-N-spiro[3.4]octan-3-yl-pyridine-2-carboxamide (P-6), 2-[(2,6-difluoro-4-pyridyl)amino]-N-Petition 870250055585, dated 01 / 07 / 2025, page 66 / 501 53 / 236 isopentyl-5-methoxy-pyrimidine-4-carboxamide (P-9), 2-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-5-methoxypyrimidine-4-carboxamide (P-10), 6-(N-cyano-3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxy-pyridine-2-carboxamide (P-20), 6-(3,5-difluoroanilino)-N-(2,2dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-22), 6(3,5-difluoroanilino)-3-methoxy-N-(2-phenylpropyl)pyridine-2-carboxamide (P-23), N-benzyl-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-25), 6-(3,5-difluoroanilino)-N-[(3,5-difluorophenyl)methyl]-3-methoxypyridine-2-carboxamide (P-26), 6-(3,5-difluoroanilino)-N[2-(4-fluorophenoxy)ethyl]-3-methoxy-pyridine-2-carboxamide (P-27), 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-30), 6(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-ethoxypyridine-2-carboxamide (P-44), 6-(3,5-difluoroanilino)-N[2-(4-fluorophenoxy)cyclobutyl]-3-methoxy-pyridine-2-carboxamide (P-45), 6-[(2,6-difluoro-4-pyridyl)amino]-3-methoxy-N-[5-(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-47), 6-(3,5-difluoroanilino)-3-methoxy-N-[5(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-55), 6-(3,5-difluoroanilino)-3-methoxy-N-[6(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-56), 6-(3,5-difluoroanilino)-3-methoxy-N-[(4phenoxyphenyl)methyl]pyridine-2-carboxamide (P-57), 6-(3,5difluoroanilino)-N-[(2,2-difluoro-1,3-benzodioxol-4yl)methyl]-3-methoxypyridine-2-carboxamide (P-58), 6-(3,5difluoroanilino)-3-methoxy-N-(2-oxabicyclo[3.2.0]heptan-7yl)pyridine-2-carboxamide (P-59), 6-(3,5-difluoroanilino)3-methoxy-N-[[1-(trifluoromethyl)cyclopropyl]methyl]pyridine Petition 870250055585, de 01 / 07 / 2025, p. 67 / 501 54 / 236 2-carboxamide (P-62), N-(5-cyclopropyltetrahydrofuran-3yl)-6-(3,5-difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-65), 6-(3,5-difluoroanilino)-3-methoxy-N-[(8-methyl-5oxaespiro[3.5]nonan-8-yl)methyl]pyridine-2-carboxamide (P67), 6-(3,5-difluoroanilino)-3-methoxy-N-[(3-methyltetrahydrofuran-3-yl)methyl]pyridine-2-carboxamide (P-68), 6(3,5-difluoroanilino)-3-methoxy-N-(4-oxaespiro[2.4]heptan-6yl)pyridine-2-carboxamide (P-70), 6-(3,5-difluoroanilino)3-methoxy-N-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyridine-2-carboxamide (P-74), 6-(3,5-difluoroanilino)-N-(7,7-dimethyl2-oxabicyclo[3.2.0]heptan-6-yl)-3-methoxy-pyridine-2-carboxamide (P-76), 6-(isothiazol-4-ylamino)-3-methoxy-N-[5(trifluoromethyl)indan-1-yl]pyridine-2-carboxamide (P-79), N-tert-butyl-6-(3,5-difluoroanilino)-3-ethoxy-pyridine-2-carboxamide (P-94), 6-[(2,6-difluoro-4-pyridyl)amino]-N(1,5-dimethyl-hexyl)-3-methoxy-pyridine-2-carboxamide (P102), N-(2,2-dimethylcyclobutyl)-6-[(5-fluoro-3pyridyl)amino]-3-methoxy-pyridine-2-carboxamide (P-104), 6(3,5-difluoroanilino)-3-methoxy-N-(1-methylcyclohexyl)pyridine-2-carboxamide (P-108), 6-[(2,6-difluoro-4pyridyl)amino]-3-methoxy-N-(1-methylcyclopentyl)pyridine-2-carboxamide (P-109), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1-methylcyclohexyl)pyridine-2-carboxamide (P110), N-tert-butyl-6-(3,5-difluoroanilino)pyridine-2-carboxamide (P-112), 6-[(2,6-difluoro-4-pyridyl)amino]-N(2,2-dimethylpropyl)pyridine-2-carboxamide (P-113), N-tert-butyl-6-[(2,6-difluoro-4-pyridyl)amino]pyridine-2-carboxamide (P-114), N-[[3,5bis(trifluoromethyl)phenyl]methyl]-6-(3,5-difluoroanilino)-3methoxy-pyridine-2-carboxamide (P-115), N-tert-butyl-6-(3,5 Petition 870250055585, de 01 / 07 / 2025, pág. 68 / 501 55 / 236 difluoroanilino)-3-methoxy-1-oxido-pyridin-1-ium-2-carboxamide (P-117), 6-(3,5-difluoroanilino)-N-(1methylcyclopentyl)pyridine-2-carboxamide (P-119), N-(3cyanothietan-3-yl)-6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxamide (P-121), 6-(3,5-difluoroanilino)-3methoxy-N-(3-methyltetra-hydrofuran-3-yl)pyridine-2-carboxamide (P-122), N-(1-cyanocyclopentyl)-6-(3,5difluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-123), 6-(3-chloro-5-fluoro-anilino)-N-(2,2-dimethylpropyl)-3methoxy-pyridine-2-carboxamide (P-134), N-(2,2dimethylpropyl)-6-(3-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-139), N-(2,2-dimethylpropyl)-3-methoxy-6(3,4,5-trifluoroanilino)pyridine-2-carboxamide (P-145), Ntert-butyl-6-(3-cyanoanilino)-3-methoxy-pyridine-2-carboxamide (P-146), N-tert-butyl-6-(3-cyano-5-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-147), N-tert-butyl-6-(3,5-dichloroanilino)-3-methoxy-pyridine-2-carboxamide (P-148), N-tert-butyl-6-(3-chloro-5-fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-152), N-tert-butyl-6-(4-chloro-3,5-difluoro-anilino)-3-methoxy-pyridine-2-carboxamide (P-153), N-tert-butyl-6-(3-chloroanilino)-3methoxy-pyridine-2-carboxamide (P-155), 6-(3,5difluoroanilino)-N-(1,2-dimethylpropyl)-3-methoxy-pyridine-2-carboxamide (P-168), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1,2,2-trimethylpropyl)pyridine-2-carboxamide (P169), 6-(3,5-difluoroanilino)-3-methoxy-N-(1,2,2trimethylpropyl)pyridine-2-carboxamide (P-170),6-(3,5difluoroanilino)-3-methoxy-N-(1,1,2,2tetramethylpropyl)pyridine-2-carboxamide (P-171), 6-[(2,6difluoro-4-pyridyl)amino]-3-methoxy-N-(1,1,2Petição 870250055585, de 01 / 07 / 2025, pág. 69 / 501, 56 / 236 trimetilpropil)piridina-2-carboxamida (P-173), 6-[(2,6difluoro-4-piridil)amino]-3-metoxi-N-(1,1,2,2tetrametilpropil)piridina-2-carboxamida (P-174), N-[1-(6cloro-2-piridil)ciclobutil]-6-(3,5-difluoroanilino)-3metoxi-piridina-2-carboxamida (P-177), 6-[(2,6-difluoro-4piridil)amino]-N-(1-isopropilciclobutil)-3-metoxi-piridina2-carboxamida (P-181), N-[3-(4-clorofenil)ciclobutil]-6(3,5-difluoroanilino)-3-metoxi-piridina-2-carboxamida (P187), 6-(N-acetil-3,5-difluoro-anilino)-N-(2,2dimetilciclobutil)-3-metoxi-piridina-2-carboxamida (P-189), N-terc-butil-6-(2-cloro-3,5-difluoro-anilino)-3-metoxipiridina-2-carboxamida (P-190), 6-[(2,6-difluoro-4piridil)amino]-N-(2,2-dimetilciclobutil)-3-metoxi-piridina2-carboxamida (P-4), 6-(3,5-difluoroanilino)-N-(2,2dimetilciclobutil)-3-metoxi-piridina-2-carboxamida (P-7), N-tert-butil-6-[(2,6-difluoro-4-pyridyl)amino]-3-methoxypyridina-2-carboxamide (P-91), N-tert-butil-6-(3,5difluoroanilino)-3-methoxy-pyridina-2-carboxamide (P-93), 6(3,5-difluoroanilino)-3-methoxy-N-(1metilciclopentyl)pyridin-2-carboxamide (P-107), 6-(3,5difluoroanilino)-3-methoxy-N-(1-metilciclobutil)pyridine-2carboxamide (P-118), 6-[(2,6-difluoro-4-pyridyl)amino]-N(1-metilciclopentyl)pyridine-2-carboxamide (P-120), 6[(2,6-difluoro-4-pyridyl)amino]-3-methoxy-N-(1metilciclobutil)pyridine-2-carboxamide (P-127), N-tertbutil-6-[(2-fluoro-4-pyridyl)amino]-3-methoxy-pyridina-2carboxamide (P-156), N-tert-butil-6-(3-fluoroanilino)-3methoxy-pyridin-2-carboxamide (P-160), N-tert-butil-3methoxy-6-(3,4,5-trifluoroanilino)pyridin-2-carboxamide (P162), 6-(3,5-difluoroanilino)-3-methoxy-N-(1,1,2Petição 870250055585, de 01 / 07 / 2025, pág. 70 / 501 57 / 236 trimetilpropil)piridina-2-carboxamida (P-172), N-(1ciclobutilciclobutil)-6-(3,5-difluoroanilino)-3-metoxipiridina-2-carboxamida (P-176), 6-(3,5-difluoroanilino)-N(1-etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-178), 6- (3,5-difluoroanilino)-N-(1-isopropilciclobutil)-3-metoxipiridina-2-carboxamida (P-179), N-(1-terc-butilciclobutil)6-(3,5-difluoroanilino)-3-metoxi-piridina-2-carboxamida (P180), 6-[(2,6-difluoro-4-piridil)amino]-N-(1etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-183), and N-(1-terc-butilciclobutil)-6-[(2,6-difluoro-4piridil)amino]-3-metoxi-piridina-2-carboxamida (P-185).
[0084] More preferably, the compound according to formula (I) is selected from 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-3-methoxypyridine-2-carboxamide (P-4), 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxypyridine-2-carboxamide (P-7), N-tert-butyl-6-[(2,6-difluoro-4-pyridyl)amino]-3-methoxypyridine-2-carboxamide (P-91), N-tert-butyl-6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxamide (P-93), 6-(3,5-difluoroanilino)-3-methoxy-N-(1-methylcyclopentyl)pyridine-2-carboxamide (P107), 6-(3,5-difluoroanilino)-3-methoxy-N-(1methylcyclobutyl)pyridine-2-carboxamide (P-118), 6-[(2,6difluoro-4-pyridyl)amino]-N-(1-methylcyclopentyl)pyridine-2carboxamide (P-120), 6-[(2,6-difluoro-4-pyridyl)amino]-3methoxy-N-(1-methylcyclobutyl)pyridine-2-carboxamide (P-127), N-tert-butyl-6-[(2-fluoro-4-pyridyl)amino]-3-methoxypyridine-2-carboxamide (P-156), N-tert-butyl-6-(3fluoroanilino)-3-methoxy-pyridine-2-carboxamide (P-160), N-tert-butyl-3-methoxy-6-(3,4,5-trifluoroanilino)piridina-2, Petição 870250055585, de 01 / 07 / 2025, pág. 71 / 501 58 / 236 carboxamida (P-162), 6-(3,5-difluoroanilino)-3-metoxi-N(1,1,2-trimetilpropil)piridina-2-carboxamida (P-172), N-(1ciclobutilciclobutil)-6-(3,5-difluoroanilino)-3-metoxipiridina-2-carboxamida (P-176), 6-(3,5-difluoroanilino)-N(1-etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-178), 6-(3,5-difluoroanilino)-N-(1-isopropilciclobutil)-3-metoxipiridina-2-carboxamida (P-179), N-(1-terc-butilciclobutil)6-(3,5-difluoroanilino)-3-metoxi-piridina-2-carboxamida (P180), 6-[(2,6-difluoro-4-piridil)amino]-N-(1etilciclobutil)-3-metoxi-piridina-2-carboxamida (P-183), and N-(1-terc-butilciclobutil)-6-[(2,6-difluoro-4piridil)amino]-3-metoxi-piridina-2-carboxamida (P-185).
[0085] The compounds of the present invention can be prepared as shown in the following schemes, in which, unless otherwise stated, the definition of each variable is as defined above for a compound of formula (I).
[0086] The process according to the invention for preparing compounds of formula (I) is carried out by methods known to those skilled in the art, and described in greater detail below. For example, compounds of formula (I) can be prepared by the reaction of a carboxylic acid of formula (II): O I H (II) where R1, R2, R3, A and R5 are as defined in formula (I), with an amine of formula (III): Petition 870250055585, dated 01 / 07 / 2025, p. 72 / 501 59 / 236 HR N EU |_| (III) where R4 is as defined in formula (I), under various conditions well known to those skilled in the art, some of which are outlined in Scheme 1. Diagram 1: (COC^^ inert solvent, e.g. CH^CI^ta or SOCI2,CH2CI2ta ° or DCC, EDO. 7HF or pyridine, RT at 120 °C or T3P®, pyridine or HATU, base, DMF optionally in the presence of a basis, R·^ R (I) R3O P-ex· Et3N,pyridine >C = halogen
[0087] As shown in Scheme 1, the compounds of formula (II) where R1 R2, R3, A and R5 as defined in formula (I) are activated to compounds of formula (lia) by methods known to those skilled in the art and described, for example, in Tetrahedron, 61 (46), 10827-10852, 2005. For example, compounds of formula lia in which Xo is a halogen are formed by treating compounds of formula (II) with, for example, oxalyl chloride or thionyl chloride in the presence of catalytic amounts of DMF in inert solvents such as methylene dichloride or THF at temperatures between 25-170 °C, preferably 25-80 °C. Treatment of (lia) with compounds of formula (III), in which R4 is as defined in formula (I), optionally in Petition 870250055585, dated 01 / 07 / 2025, page 73 / 501 60 / 236 The presence of a base, for example triethylamine or pyridine, leads to compounds of formula (I). Alternatively, compounds of formula (I) can be prepared by treating compounds of formula (II) with dicyclohexyl carbodiimide (DCC) or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) to give the activated species (IIa), wherein Xo is X01 or X02, in an inert solvent, for example pyridine or THF, optionally in the presence of a base, for example triethylamine, at temperatures between 50-180 °C. Additionally, an acid of formula (II) can also be activated by reaction with a coupling reagent such as propanephosphonic acid anhydride (T3P®) or O-(7-Aza1-benzotriazolyl)-N,N,N',N'-tetramethyluroniumhexafluorophosphate (HATU) to provide compounds of formula IIa wherein Xo is X03 and X04 as described for example in Synthesis 2013, 45, 1569 and Journal Prakt. Chemie 1998, 340, 581. The subsequent reaction with an amine of formula (III) yields compounds of formula (I).
[0088] The intermediates of formula (II): (II) where R1, R2, and R5 are as defined in formula (I), can be prepared from the compounds of formula (IV): Petition 870250055585, dated 01 / 07 / 2025, p. 74 / 501 61 / 236 5 RR (IV) where R1, R2, R3 and R5 are as described in formula (I) and R10 is C1-C1 alkyl, by acid or base hydrolysis. For example, compounds of formula (IV) in which R10 is t-butyl, after treatment with mineral acids or trifluoroacetic acid in an inert solvent, such as methylene chloride or dioxane, lead to compounds of formula (II). Alternatively, the base hydrolysis of compounds of formula (IV), in which R10 is, for example, methyl, ethyl, isopropyl and the like, with aqueous alkaline earth metal bases, such as lithium, sodium or potassium hydroxides, optionally in the presence of a water-miscible solvent, such as THF, dioxane, acetone and the like, leads to compounds of formula (II). Such reactions are well known to those skilled in the art.
[0089] Compounds of formula (IV) can be prepared by reacting compounds of formula (V): (V) wherein R2, R3, R10 and A are as described above, and Xa1 is chlorine, bromine, iodine, aryl sulfonate, alkyl sulfonate or trifluoromethane sulfonate, with compounds of formula (VI): R1I 5 NH R (VI) where R5 is chlorine, bromine, iodine, arylsulfonate, alkylsulfonate or trifluoromethanesulfonate, Petition 870250055585, dated 01 / 07 / 2025, page 75 / 501 62 / 236 with compounds of formula (VI): The Buchwald-Hartwig reaction is well known to those skilled in the art and is a chemical reaction used in organic chemistry for the synthesis of carbon-nitrogen linkages through palladium-catalyzed coupling reactions of amines with aryl and heteroaryl halides and sulfonates. Such reactions have been reported in, for example, ACS catal., 2019, 3822-3830 and references cited therein. The reaction typically involves a palladium catalyst such as Pd(OAc)2, Pd2(dba)3 and ligands such as diphenylphosphinobinaphthyl (BINAP), diphenylphosphinoferrocene (DPPF) and Xathphos. More modern Buchwald-Hartwig coupling methods involve the use of palladium precatalysts such as BrettPhos Pd G3 (CAS[1470372-59-8]) or RuPhos Pd G3 (CAS [1445085-77-7]), the use of which ensures the efficient and rapid generation of the active catalytic species.The reaction requires the presence of bases such as alkaline earth metal alkoxides and hydroxides, for example potassium or sodium t-butoxides or hydroxides, alkaline earth metal carbonates such as sodium or cesium carbonates, and organic bases such as 1,8Diazabicyclo[5.4.0]undec-7-ene (DBU). The reactions are carried out in a variety of inert solvents such as THF, water, toluene, dioxane and DMF and / or their mixtures at temperatures between 20-170 °C (Buchwald, SL Chem. Rev., 2016. 116(19), 12564). The reaction is especially favorable in cases where R1 is hydrogen.
[0090] The chemistry for the synthesis of compounds of formula (I) is summarized in Scheme 2. Scheme 2: Petition 870250055585, dated 01 / 07 / 2025, page 76 / 501 63 / 236 H R^'R5(VD Amination Buchwald-Hartwig hydrolysis of an acid or base ester (COCÍ)2, inert solvent, e.g. la or SOCL^CH^ia011DCC, EDO, THF or pyridine. ta at 120CC or T3PO, pyridine or HATU, base, DMF halogen
[0091] Experts in the art will recognize that the order of the reactions can be altered and compounds of formula (I) can also be synthesized as shown in Scheme 3 Scheme 3: (COCI}2, inert solvent, e.g. CF^CIjia or SOC^CH^ia611DCC, EDC. THF or pyridine, water 12Ú *C qu T3P©, pyridine or HATU. base. DMF ,R4(HO optionally in the presence of a base, e.g. Ei^N. pyridine H (VII) Amination Buchwald-Hartwig Petition 870250055585, dated 01 / 07 / 2025, p. 77 / 501 64 / 236
[0092] As shown in Scheme 3, esters of formula (V) can be hydrolyzed into compounds of formula (Va) by methods previously discussed and known to those skilled in the art. Acids of formula (Va) can be activated into compounds of formula (Vb), wherein Xo is a halogen or Xoi, Xo2, Xo3 or Xo4 as previously defined, also using methods previously discussed, which after treatment with compounds of formula (III) under the conditions discussed in Scheme 2, lead to compounds of formula (VII). The previously discussed Buchwald-Hartwig amination of compounds of formula (VII) with compounds of formula (VI) leads to compounds of formula (I).
[0093] A further synthesis of compounds of formula (I) is shown in Scheme 4: Scheme 4: Aminaçae Buchwald-Hartwig H R (Vi) (COCÍ}2, only inert, e.g. la R —Xa Alkylation Solvent e.g. DMF or AcCN base e.g. Alkaline earth metal carbonate
[0094] As in formula (Vc), where A, R1, previously and R3 is hydroxyl, of formula (Vila) using the in Scheme 4, the compounds of R2e Xa1, as described, are converted into Buchwald-Hartwig chemical compounds. Petition 870250055585, dated 01 / 07 / 2025, page 78 / 501 65 / 236 previously described. The compounds of formula (VIIa) thus obtained have their carboxyl group activated by methods previously described to give compounds of formula (Viib), which after treatment with compounds of formula (III) also as described above, lead to compounds of formula (Ia). The compounds of formula Ia can be converted into compounds of formula Ib by an alkylation reaction, well known to those skilled in the art. For example, the reaction of compounds of formula Ia with a compound of formula Rn-Xa2, where R11 is C1-Cealkyl, C1-Cehaloalkyl, C3-Cehalocycloalkyl, C2-Cealkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C1C6cyanoalkyl, C1-C6alkoxyC1-C3alkyl, C3-C6cycloalkylC1C2alkyl, oxetan-3-yl, or oxetan-3-yl-CH2-, and Xa2 is a halogen, in the presence of a base, such as cesium, sodium, or potassium carbonate, and an inert solvent, such as DMF or acetonitrile, leads to compounds of formula Ib.Compounds of formula Ia can also be prepared from compounds of formula (Ib), wherein R11 is methyl, by treatment with pyridinium chloride optionally in the presence of a solvent at temperatures between 50-170 °C, or by melting in the presence of a solvent. This is shown in Scheme 5. Scheme 5: Petition 870250055585, dated 01 / 07 / 2025, p. 79 / 501 66 / 236 (lb) (la)
[0095] Compounds of formula (I) in which R1 is cyano, C1-Cealkylcarbonyl and C1-Cealkoxycarbonyl can be prepared by methods well known to those skilled in the art. For example, compounds in which R1 is C1-Cealkylcarbonyl and C1-Cealkoxycarbonyl can be obtained as shown in Scheme 6. Scheme 6: {COCI)2, inert only, eg Ia ¢11 SOCÇ CH?CI21awDC-C, EDC. 1HF or pyridine. ti at 120 ΐo73P®Fpyridrna π «u HATU, base, DMF r13^oh-----------------(VIII) (Villa) Optionally in the presence of a base, ρ.»ϊ. EÇl pírídím
[0096] As shown in Scheme 6, compounds of formula (VIII), where Rla is C1-Cealkyl or C1-Cealkoxy, can be activated into compounds of formula (Villa) by methods shown in Scheme 2 and as discussed previously in Scheme 1. The subsequent reaction of compounds of formula (Villa) or (VIII) with compounds of formula (Ic), Petition 870250055585, dated 01 / 07 / 2025, p. 80 / 501 67 / 236 optionally in the presence of a base, leads to compounds of formula (Id).
[0097] Compounds of formula (I), wherein R2, R3, R4 and A are as defined for formula (I), and R1 is cyano, namely compounds of formula (Ie), can be obtained by reacting a compound of formula (IX), wherein Xa3 is halogen, preferably bromine, by thermal heating or with the aid of a base, such as sodium hydride, butyllithium or an organic base such as pyridine, in an inert solvent such as THF, dioxane, methylene chloride and the like with compounds of formula (Ic). This is shown in Scheme 7. Scheme 7: Xa-—= N (IX) Optionally a base; Solvent
[0098] Similar reactions have been reported in the literature, for example in Eu. J. Chem., 24 (52), 13788-13791, 2018, Org. Lett., 19(14), 3835-3838, 2017, and Synthesis, 3077-3088, 2009.
[0099] The compounds of formula (III), (VI), (V) and (VIII) are commercially available or are known in the literature. Petition 870250055585, dated 01 / 07 / 2025, p. 81 / 501 68 / 236
[00100] Surprisingly, it has now been discovered that the new compounds of formula (I) have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases caused by fungi.
[00101] The compounds of formula (I) can be used in the agricultural sector and related areas of use, for example, as active ingredients for plant pest control or in non-living materials for the control of microorganisms or organisms that cause deterioration or organisms potentially harmful to humans. The new compounds are distinguished by excellent activity at low application rates, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and can be used for the protection of numerous cultivated plants. The compounds of formula (I) can be used to inhibit or destroy pests that occur on plants or plant parts (fruit, flowers, leaves, stems, tubers, roots) of different useful plant crops, while at the same time also protecting those plant parts that grow later, for example, from phytopathogenic microorganisms.
[00102] The present invention further relates to a method for controlling or preventing infestation of plants or plant propagation material and / or food crops collected that are susceptible to microbial attack by treating plants or plant propagation material and / or food crops collected in Petition 870250055585, dated 01 / 07 / 2025, page 82 / 501 69 / 236 that an effective amount of a compound of formula (I) is applied to plants, parts thereof or locus thereof.
[00103] It is also possible to use the compounds of formula (I) as a fungicide. The term fungicide, as used in this document, means a compound that controls, modifies or prevents the growth of fungi. The term effective amount in fungicidal terms means the amount of such a compound or combination of such compounds that is capable of producing an effect on fungal growth. Control or modification effects include any deviation from natural development, such as death, retardation and the like, and prevention includes barrier or other defensive formation on or over a plant to prevent fungal infection.
[00104] It is also possible to use the compounds of formula (I) as coating agents for the treatment of plant propagation material, for example, seed, such as fruits, tubers or grains or plant cuttings (e.g., rice), for protection against fungal infections, as well as against phytopathogenic fungi occurring in the soil. The propagation material can be treated with a composition comprising a compound of formula (I) before planting: the seed, for example, can be coated before being sown.
[00105] The active ingredients according to the invention can also be applied to grains (coating), by impregnating the seeds in a liquid formulation or by coating them with a solid formulation. The composition can also be applied to the planting site when the propagation material is being planted, for example, to Petition 870250055585, dated 01 / 07 / 2025, page 83 / 501 70 / 236 seed furrow during sowing The invention also relates to such methods of treating plant propagation material and to plant propagation material thus treated.
[00106] Furthermore, the compounds according to the present invention can be used to control fungi in related areas, for example in the protection of technical materials, including wood and wood-related technical products, in food storage, and in hygiene management.
[00107] Additionally, the invention could be used to protect non-living materials from fungal attack, for example, construction timber, wall panels and paint.
[00108] The compounds of formula (I) may be, for example, effective against fungi and fungal disease vectors as well as phytopathogenic bacteria and viruses. These fungi and fungal disease vectors, as well as phytopathogenic bacteria and viruses, are for example: Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp. including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea, Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans, Ceratocystis spp, Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp, Claviceps purpurea, Coccidioides immitis, Petition 870250055585, dated 01 / 07 / 2025, p. 84 / 501 71 / 236 Cochliobolus spp, Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechslera spp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa lata, Fusarium spp. including F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasma spp. including H. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp, Penicillium spp. including P. digitatum, P.italicum, Petriellidium spp, Peronosclerospora spp. including P. maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp, Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans, Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp, Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopeziza tracheiphila, Puccinia spp. including P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp, Pyricularia spp. Petition 870250055585, dated 01 / 07 / 2025, p. 85 / 501 72 / 236 including P. oryzae, Pythium spp. including P. ultimum, Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus, Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp, Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp, Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp., including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp, Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturia spp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.
[00109] Within the scope of the present invention, target crops and / or useful plants to be protected typically comprise perennial and annual crops, such as berries, for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example barley, corn, millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example cotton, flax, hemp, jute and sisal; field crops, for example sugar beet and fodder beet, coffee, hops, mustard, rapeseed (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, for example apple, apricot, avocado, banana, cherry, citrus fruits, nectarine, peach, pear and plum; grasses, for example Bermuda grass, bluegrass, ragweed, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, Petition 870250055585, dated 01 / 07 / 2025, p. 86 / 501 73 / 236 chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes, for example beans, lentils, peas and soybeans; nuts, for example almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms, for example palm oil; ornamental plants, for example flowers, shrubs and trees; other trees, for example cocoa, coconut, olive and rubber; vegetables and greens, for example asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, pumpkin, melon, okra, onions, peppers, potatoes, butternut squash, rhubarb, spinach and tomatoes; and vines, for example grapes.
[00110] The term “useful plants” should be understood as also including useful plants that have been made tolerant to herbicides, such as bromoxynil, or classes of herbicides (such as, for example, inhibitors of HPPD inhibitors, ALS inhibitors, for example, primisulfuron, prosulfuron, and trifloxysulfuron, EPSPS (5-enolpyrovilshikimate-3-phosphate synthase) inhibitors, GS (glutamine synthetase) inhibitors, or PPO (protoporphyrinogen oxidase) inhibitors as a result of conventional breeding or genetic engineering methods. An example of a crop that has been made tolerant to imidazolinones, for example, imazamox, by conventional breeding methods (mutagenesis), is Clearfield® summer rapeseed (Canola). Examples of crops that have been made tolerant to herbicides or herbicide classes by genetic modification methods include commercially available glyphosate- and glufosinate-resistant maize varieties. Petition 870250055585, dated 01 / 07 / 2025, page 87 / 501 74 / 236 available under the trade names RoundupReady®, Herculex I® and LibertyLink®.
[00111] The term “useful plants” is to be understood as also including useful plants that have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
[00112] Examples of such plants are: YieldGard® (a variety of maize that expresses a Cry(IA)(b) toxin); YieldGard Rootworm® (a variety of maize that expresses a CryIIIB(b1) toxin); YieldGard Plus® (a variety of maize that expresses a Cry(IA)(b) toxin and a CryIIIB(b1) toxin); Starlink® (a variety of maize that expresses a toxin Cry9(c)); Herculex I® (a variety of maize that expresses a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to provide tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a variety of cotton that expresses a Cry(IA)(c) toxin); Bollgard I® (a variety of cotton that expresses a Cry(IA)(c) toxin); Bollgard II® (a variety of cotton that expresses a Cry(IA)(c) toxin and a CryI(IA)(b) toxin); VIPCOT® (a variety of cotton that expresses a VIP toxin); NewLeaf® (a variety of potato that expresses a CryII(IA) toxin); NatureGard® Agrisure® GT Advantage (glyphosate tolerance trait GA21), Agrisure® CB Advantage (corn borer (CB) trait Bt11), Agrisure® RW (corn rootworm trait) and Protecta®. Petition 870250055585, dated 01 / 07 / 2025, page 88 / 501 75 / 236
[00113] The term “cultures” is to be understood as also including culture plants that have been so transformed by the use of recombinant DNA techniques that they are capable of synthesizing one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.
[00114] Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins from nematode-colonizing bacteria, for example, Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomyces toxins, plant lectins, such as pea lectins, barley lectins or white bellflower lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin inhibitors, cystatin, papain; ribosome-inactivating proteins (RIPs), such as ricin, corn RIP, abrin, lufin, saporin or briodin; enzymes of steroid metabolism, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP glycosyltransferase, cholesterol oxidases, inhibitors of. Petition 870250055585, dated 01 / 07 / 2025, page 89 / 501 76 / 236 ecdysone, HMG-CoA reductase, ion channel blockers such as sodium or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.
[00115] In the context of the present invention, δ-endotoxins are to be understood as, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example, Vip1, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by a novel combination of different domains of these proteins (see, for example, WO 02 / 15701). Truncated toxins are known, for example a truncated Cry1Ab. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are substituted. In such amino acid substitutions, preferably protease recognition sequences not naturally present are inserted into the toxin, such as, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into a Cry3A toxin (see WO 03 / 018810).
[00116] Examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed, for example, in EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073. The processes for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are Petition 870250055585, dated 01 / 07 / 2025, page 90 / 501 77 / 236 known, for example, from WO 95 / 34656, EP-A-0 367 474, EPA-0 401 979 and WO 90 / 13651.
[00117] The toxin contained in transgenic plants gives the plants tolerance to harmful insects. These insects can occur in any taxonomic group of insects, but are especially commonly found in beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).
[00118] Transgenic plants containing one or more genes that encode insecticide resistance and express one or more toxins are known, and some of them are commercially available.Examples of such plants are: YieldGard® (a variety of corn that expresses a Cry1Ab toxin); YieldGard Rootworm® (a variety of corn that expresses a Cry3Bb1 toxin); YieldGard Plus® (a variety of corn that expresses a Cry1Ab and a Cry3Bb1 toxin); Starlink® (a variety of corn that expresses a Cry9C toxin); Herculex I® (a variety of corn that expresses a Cry1Fa2 toxin and the enzyme phosphinothricin-N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a variety of cotton that expresses a Cry1Ac toxin); Bollgard I® (a variety of cotton that expresses a Cry1Ac toxin); Bollgard II® (a variety of cotton that expresses a Cry1Ac and a Cry2Ab toxin); VipCot® (cotton variety expressing Vip3A and Cry1Ab toxin); NewLeaf® (potato variety expressing Cry3A toxin); NatureGard®, Agrisure®GT Advantage (glyphosate-tolerant trait GA21), Agrisure®CB Advantage (corn borer (CB) trait Bt11) and Protecta®. Petition 870250055585, dated 01 / 07 / 2025, page 91 / 501 78 / 236
[00119] Additional examples of such transgenic crops are: 1. Bt11 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays that has been made resistant to attack by the European maize borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylAb toxin. Bt11 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176 maize from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified Zea mays that has been made resistant to attack by the European maize borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176 maize also transgenically expresses the PAT enzyme to achieve tolerance to the herbicide glufosinate ammonium. 3. Maíz MIR604 from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Maize that has been made insect-resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in document WO 03 / 018810. 4. MON 863 corn from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and has resistance to certain Coleoptera insects. Petition 870250055585, dated 01 / 07 / 2025, page 92 / 501 79 / 236 5. IPC 531 Cotton from Monsanto Europe SA, 270272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02. 6. Corn 1507 from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified corn to express the Cry1F protein in order to achieve resistance to certain Lepidoptera insects, and the PAT protein in order to achieve tolerance to the herbicide glufosinate ammonium. 7. Monsanto Europe SA NK603 x MON 810 corn 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It consists of conventionally improved hybrid maize varieties obtained by crossing the genetically modified varieties NK603 and MON 810. The NK603 x MON 810 maize transgenically expresses the CP4 EPSPS protein, obtained from the CP4 strain of Agrobacterium sp., which confers tolerance to the herbicide Roundup® (contains glyphosate), and also a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki that confers tolerance to certain Lepidoptera, including the European corn borer.
[00120] The term locus, as used herein, designates fields in which or on which plants are growing or where seeds of cultivated plants are sown or where seeds will be placed in the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
[00121] The term plants refers to all the physical parts of a plant, including seeds, seedlings, young plants, roots, tubers, stems, stalks, foliage, and fruits. Petition 870250055585, dated 01 / 07 / 2025, p. 93 / 501 80 / 236
[00122] The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. Examples may include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and plant parts. It may also include germinated plants and young plants to be transplanted after germination or emergence from the soil. These young plants may be protected before transplanting by total or partial immersion treatment. Preferably, “plant propagation material” is understood to denote seeds.
[00123] Pesticides referred to here using their common name are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.
[00124] The compounds of formula (I) may be used in unmodified form or, preferably, in conjunction with the adjuvants conventionally employed in the formulation technique. For this purpose they may conveniently be formulated in a known manner in emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granules and also encapsulations, e.g., in polymeric substances. As with the type of compositions, the methods of application, such as spraying, atomizing, dusting, dispersing, coating or pouring, are chosen according to the intended objectives and the circumstances. Petition 870250055585, dated 01 / 07 / 2025, p. 94 / 501 81 / 236 prevalent. The compositions may also contain other adjuvants, such as stabilizers, antifoaming agents, viscosity regulators, binders or tack promoters, as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.
[00125] Suitable carriers and adjuvants, for example for agricultural use, may be solid or liquid, and are substances useful in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tack promoters, thickeners, binders or fertilizers. Such carriers are, for example, described in WO 97 / 33890.
[00126] The compounds of formula (I) are normally used in the form of compositions and may be applied to the area of the crop or plant to be treated, simultaneously or in succession with additional compounds. These additional compounds may be, for example, fertilizers or micronutrient donors or other preparations that influence plant growth. They may also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired, together with additional carriers, surfactants or application enhancers commonly used in the formulation technique.
[00127] Compounds of formula (I) can be used in the form of compositions (fungicides) to control or protect against phytopathogenic microorganisms, Petition 870250055585, dated 01 / 07 / 2025, page 95 / 501 82 / 236 comprising as an active ingredient at least one compound of formula (I) or at least one preferred individual compound as defined above, in free form or in the form of an agrochemically usable salt, and at least one of the aforementioned adjuvants.
[00128] The invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I), an agriculturally acceptable carrier, and optionally an adjuvant. An agriculturally acceptable carrier is, for example, a carrier that is suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, said composition may comprise at least one or more active compounds in terms of pesticides, for example, an additional fungicidal active ingredient in addition to the compound of formula (I).
[00129] The compound of formula (I) may be the sole active ingredient in a composition or may be mixed with one or more additional active ingredients such as a pesticide, fungicide, synergistic agent, herbicide or plant growth regulator, as appropriate. An additional active ingredient may, in some cases, result in unexpected synergistic activities.
[00130] Examples of suitable additional active ingredients include the following acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, arylphenylketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, Petition 870250055585, dated 01 / 07 / 2025, page 96 / 501 83 / 236 benzothiazole fungicides, botanical fungicides, diphenyl bridging fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, organophosphate fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, fungicides of quinoline, quinone fungicides, quinoxaline fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides,Triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides.
[00131] Examples of suitable additional active ingredients also include the following: petroleum oils, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, benzenesulfonate, 2,4-dichlorophenyl, 2-fluoro-N-methyl-N-1-naphthylacetamide, sulfone, 4-chlorophenylphenyl, acetoprole, aldoxicarb, amidione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramite, arsenous oxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, bixafen, brofenvalerate, bromocyclen, bromofos, Petition 870250055585, dated 01 / 07 / 2025, page 97 / 501 84 / 236 bromopropilato, buprofezin, butilcarboximetilcálcio, butoxicarboximetilcálcio, butoxicarboximetilcarboximetila, butoxicarboximetilcálcio, butoxicarboximetoxicarboximeto carbanolato, carbofenotion, cimiazol, quinometionato, clorbenzida, clordimeform, cloridrato clordimeform, clorfenetol, clorfensão, clorfensulfida, clorobenzilato, cloromebuform, clorometiuron, cloropropilato, clortiofos, cinerina I, cinerina II, cinerins, closantel, coumafos, crotamiton, crotoxifos, cufraneb, ciantoato, DCPM, DDT, demefion, demefion-O, demefion-S, demeton-metil, demeton-O, demeton-O-metil, demeton-S, demeton-S-metil, demeton-Smetilsulfon, diclofluanida, diclorvos, diclifos, dienocloro, dimefox, dinex, dinex-diclexina, dinocap-4, dinocap-6, dinocton, dinopenton, dinossulfon, dinoterbon, dioxation, difenilsulfona, disulfiram, DNOC, dofenapinomectina, doramectina, eprinomato-metil, etrimfos, fenazaflor, óxido de fenbutatina, fenotiocarbe, fenpirade, fenpirroximato, fenpirazamina, fenson, fentrifanil,flubenzimine, flucicloxuron, fluenetil, fluorbenside, FMC 1137, formetanate, formetanate hydrochloride, formparanate, gammaHC, gliodin, halfenprox, hexadecyl cyclopropanecarboxylate, isocarbofos, jasmolin I, jasmolin II, jodfenfos, lindane, malonoben, mecarbam, mephospholan, mesulfen, metacrifos, methyl bromide, metolcarb, mexacarbate, milbemicin oxime, mipafox, monocrotofos, morphothion, moxidectin, naled, 4chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, nifluridide, niquomycins, nitrilacarb, nitrilacarb zinc chloride complex 1:1, omethoate, oxideprofos, oxidisulfoton, pp'-DDT, parathion, permethrin, fenquapton, phosalone, phospholan, phosfamidon, Petition 870250055585, dated 01 / 07 / 2025, page 98 / 501 85 / 236 polychloroterpenes, polinactinas, proclonol, promacil, propoxur, protidationa, protoate, pyrethrin I, pyrethrin II, pyrethrinas, pyridafenthion, pyrimitate, quinalfos, quintiofos, R-1492, phosglycine, rotenona, scradan, sebufos, selamectin, sofamida, SSI-121, sulfiram, sulfluramid, sulfotep, enxofre, diflovidazin, tau-fluvalinate, TEPP, terbam, tetradifon, tetrasul, thiafenox, thiocarboxime, thiofanox, thiometon, thioquinox, turingiensin, triamifos, triarateno, triazofos, triazuron, tripenofos, trinactin, vamidotion, vaniliprole, betoxazin, dioctanoato de cobre, sulfato de cobre, cibutrina, diclona, diclorofen, endotal, fentin, lima hidratada, nabam, quinoclamina, quinonamid, simazina, acetate de tripheniltina, hidróxido de tripheniltina, crufomato, piperazine, thiophanate, cloralose, fention, piridin-4-amina, strychnine, 1-hidroxi-1H-piridine2-tiona, 4-(quinoxalin-2-ilamino)benzenesulfonamida, sulfato de 8-hidroxiquinolina, bronopol, hidróxido de cobre, cresol, dipiritiona, dodicin,fenaminosulf, formaldeído, hidrargafen, casugamicina, hidrato de cloridrato de casugamicina, bis(dimetilditiocarbamato) de níquel, nitrapirin, octilinona, ácido oxolínico, oxytetraciclina, sulfato de hidroxiquinolina de potassium, probenazole, estreptomicina, sesquisulfato de estreptomicina, tecloftalam, tiomersal, Adoxofies orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Petition 870250055585, 01 / 07 / 2025, pág. 99 / 501 86 / 236 Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Neodiprion sertifer NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii, afolato, bisazir, busulfan, dimatif, hemel, hempa, metepa, metiotepa, methyl afloate, morzid, penfluron, tepa, thiohempa, thiotepa, tretamine, uredepa, acetate of (E)-dec-5-ila-comen-ila (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate, (E)-6-methy-lhept-2-en-4-ol, (E,Z)-tetradeca4,10-dien-1-yl acetate, (Z)-dodec-1-yl acetate, (Z)hexadec-11-enal, (Z)-hexadec-11-en-1-yl acetate, (Z)-hexadec-13-en-11-yl acetate, (Z)-icos-13-en-10-one, (Z)-tetradec-7-en-1-al, (Z)-tetradec-1, (Z)-tetradec-9-en-1-yl acetate, (7E,9Z)-dodeca-7,9dien-1-yl acetate, (9Z,11E)-tetradec-9,11-dien-1-yl acetate, (9Z,12E)-tetradec-9,12-en-yl acetate, 14methyloctadec-1-eno, 4-methylnonan-5-ol com 4-methylnonan-5one, alpha-multistriatin, brevicomin, codlelure, codlemona, skin, dispersion, dodec-8-in-1-yla acetate, dodec-19-yl acetate, dodec-acetate-8, dodec-acetate-8, 10-dien-1-ila, dominicalure,Ethyl 4-methyloctanoate, eugenol, frontalin, grandlure, grandlure I, grandlure II, grandlure III, grandlure IV, hexalure, ipsdienol, ipsenol, japonilure, Petition 870250055585, dated 01 / 07 / 2025, pp. 100 / 501 87 / 236 lineatin, litlure, looplure, medlure, megatomoic acid, methyl eugenol, muscalure, octadeca-2,13-dien1-yla acetate, octadeca-3,13-dien-1-yla acetate, orfralure, orictalure, ostramona, siglure, sordidine, sulcatol, tetradec-11-en-1-yla acetate, trimedlure, trimedlure A, trimedlure B1, trimedlure B2, trimedlure C, trunc-call, 2(octyltio)-ethanol, butopironoxil, butoxi(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyltoluamide, dimethyl carbamate, phthalate dimethyla, hexanediol de etila, hexamida, metoquin-butila, methylneodecanamida, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4ethylphenyl)-ethane, 1,2-dichloropropane com 1,3dichloropropene, 1-bromo-2-chloroethane, 2,2,2trichloro-1-(3,4-dichloro-phenyl)ethyl acetate, 2,2dichlorovinyl methyl phosphate 2-ethylsulfinylethyl, 2-(1,3-dithiolan-2yl)phenyl dimethylcarbamate, 2-(2butoxyethoxy)ethyl thiocyanate, methylcarbamate 2-(4,5-dimethyl-1,3dioxolan-2-yl)phenyl,2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2isovalerylindan-1,3-dione, 2-methyl(prop2-ynyl)aminophenyl methylcarbamate, 2-thiocyanatoethyl laurate, 3-bromo-1chloroprop-1-ene, dimethyl carbamate 3-methyl-1-phenylpyrazol5-yl, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate, acethione, acrylonitrile, aldrin, alosamidine, allixicarb, alpha-ecdisonea, aluminum phosphide, aminocarb, anabasine, atidathione, azamethiphos, delta endotoxins Bacillus thuringiensis, barium hexafluorosilicate, barium polysulfide, barthrin, Baier 22 / 190, Baier 22408, beta-cyfluthrin, Petition 870250055585, dated 01 / 07 / 2025, page 101 / 501 88 / 236 beta-cypermethrin, bioethanolethrin, biopermethrin, bis(2-chloroethyl) ether, borax, bromfenvinphos, bromo-DDT, bufencarb, butacarb, butatiofos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, cevadine, chlorbicycline, chlordane, chlordecone, chloroform, chloropicrin, chlorfoxim, chlorprazophos, cis-resmethrin, cismethrin, clocitrin, copper acetoarsenite, copper arsenate, copper oleate, comitate, cryollite, CS 708, cyanofenphos, cyanophos, cyclethrin, citioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dicaptone, diclofenthion, dicresyl, dicyclanyl, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilor, dimefluthrin, dimethane, dimethrin, dimethylvinphos, dimethylan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzofos, diticrophos, DSP, ecdysterone, EI 1642, EMPC, EPBP, etafos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenetacarb,fenitrothion, fenoxacrim, phenpiritrin, fensulfothion, fenthion-ethyl, flucofuron, fosmethylane, phospirate, fostietan, furatiocarb, furetrin, guazatine, guazatine acetate, sodium trithiocarbonate, halfenprox, HC, HEOD, heptachlor, heterofos, HHDN, hydrogen cyanide, hiquincarb, IPSP, isazofos, isobenzane, isodrine, isofenfos, isolane, isoprotiolane, isoxathione, juvenile hormone I, juvenile hormone II, juvenile hormone III, kelevan, quinoprene, lead arsenate, leptofos, lirimfos, lithidathione, m-cumenyl methylcarbamate, magnesium sulfide, mazidox, mecarfon, menazon, mercuric chloride, mesulfenfos, metam, potassium metamethane, sodium metamethane, methanesulfonyl fluoride, metocrotophos, Petition 870250055585, dated 01 / 07 / 2025, page 102 / 501 89 / 236 methoprene, metotrine, methoxychlor, methyl isothiocyanate, methyl chloroform, methylene chloride, methoxadiazone, mirex, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nitiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, paradichlorobenzene, methyl parathion, pentachlorophenol, pentachlorophenol laurate, F 60-38, fenkapton, fosniclor, phosphine, phosim-methyl, pyrimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, primidofos, proflutrin, promecarb, protiofos, pyrazofos, piresmethrin, quassia, quinalfos-methyl, quinothion, rafoxanide, resmethrin, rotenone, kadethrin, riania, ryanodine, sabadilla), scradan, sebufos, SI-0009, tiapronil, sodium arsenite, sodium cyanide, sodium fluoride,sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, sulprofos, tar oils, tazimcarb, TDE, tebupirimphos, temefos, teralethrin, tetrachloroethane, tricrofos, thiocyclam, thiocyclam hydrogen oxalate, thionazin, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormetafos3, tricloronat, trimetacarb, tolprocarb, triclopiricarb, triprene, veratridine, veratrin, XMC, zetamethrin, zinc phosphide, zolaprofos and meperfluthrin, tetramethylfluthrin, bis(tributylthrin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, Petition 870250055585, dated 01 / 07 / 2025, page 103 / 501 90 / 236 trifenmorph, 1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 1,1-dichlorotetrahydrothiophene, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine, benclotiaz, cytokinins, DCIP, furfural, isamidophos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenols, zeatin, potassium ethyl xanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis extract, alpha-chlorohydrin, antu, barium carbonate, bistiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuril, coumateryl, crimidine, difenacoum, difethialone, difacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropadine, flupropadine hydrochloride, norbormide, fosacetin, phosphorus, pindone, pirinurone, sciliroside, sodium fluoroacetate, thallium sulfate, warfarin, 2-(2-butoxyethoxy)-ethyl piperonylate, 5-(1,3-benzodioxol-5-yl)-3hexylcyclohex-2-enone, farnesol with nerolidol, verbutin, MGK 264, piperonyl butoxide, piprotal, propyl isomer, S421, sesamex, sesasmoline, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziramo, imanin, ribavirin, mercury oxide, thiophanate-methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furamethpir, hexaconazole, imazalil, imiben-con-azole, ipconazole, metconazole, myclobutanil, paclobutrazole, pefurazoate, penconazole, prothioconazole, pirifenox, prochloraz, Petition 870250055585, dated 01 / 07 / 2025, page 104 / 501 91 / 236 propiconazole, pirisoxazole, simeconazole, tebucon-azole, tetraconazole, triadimefon, triadime-nol, triflumizole, triticonazole, ancimidol, fenarimol, nuarimol, bupirimato, dimetirimol, etirimol, dodemorf, fenpropidin, fenpropimorf, espiroxamina, tridemorf, ciprodinil, mepanipirim, pirimetanil, fenpiclonil, fludioxonil, benalaxil, furalaxil, meta-laxil, R-metalaxil, ofurace, oxadixil, carbendazim, debacarb, fuberidazole, tiaben-dazole, clozolinato, diclozolina, miclozolina, procimi-dona, vinclozolina, boscalid, carboxina, fenfuram, flutolanil, mepronil, oxicarboxina, pentiopirad, tifluzamida, dodina, iminoctadina, azoxistrobin, dimoxistrobin, enestroburin, fenaminstrobin, flufenoxistrobin, fluoxastrobin, cresoximmetila, metomi-nostrobin, trifloxistrobin, orisastrobin, picoxistrobin, piraclostrobin, pirametostrobin, piraoxistrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimida, folpet, tolilfluanid, mistura de bordeaux, óxido de cobre,main copper, oxinacopper, nitrothal-isopropyl, edifenfos, iprobenfos, fosdifen, tolclofos-methyl, anilazine, bentiavalicarb, blasticidin-S, clononeb, chloro-ta-lo-nil, ciflufenamid, cimoxanil, cyclobutrifluram, diclocimet, diclomezine, dicloran, dietofencarb, dimetho-morph, flumorph, dithianon, etaboxam, etridiazole, famoxa-done, fenamidone, fenoxanil, ferimzone, fluazinam, fluopicolide, flusulfamide, fluxapyroxad, fenhexamide, fos-ethyl-aluminum, himexazole, iprovalicarb, ciazofamid, metasulfo-carb, metrafenone, pencicuron, phthalide, polyoxins, propamocarb, piribencarb, proquinazid, piroquilon, pyriofenone, quinoxifen, quintazene, tiadinil, triazoxide, tricyclazole, triporin, validamicin, Petition 870250055585, dated 01 / 07 / 2025, page 105 / 501 92 / 236 valifenalate, zoxamida, mandipropamid, flubeneteram, isopirazam, sedaxane, benzovindiflupir, pidiflumetofen, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid, (3',4',5'-trifluoro-biphenyl-2-yl)-amida, isoflucipram, isothianyl, dipimethitron, 6-ethyl-5,7-dioxopyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrila, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4yl]pyridine-3-carboxamida, 4-(2,6-difluorophenyl)-6-methyl-5phenyl-pyridazine-3-carbonitrila, (R)-3-(difluoromethyl)-1methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluorophenyl)-N(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, coumetoxystrobin (jiaxiangjunzi), lvbenmixianan, diclobentiazox, mandestrobin, 3-(4,4difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolona, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3quinolyl)oxy]phenyl]propan-2-ol, oxatiapiproline,tertbutyl N-[6-[[[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumid, inpirfluxam, trolprocarb, mefentrifluconazole, ipfentrifluconazole, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1dimethyl-indan-4-yl]pyridine-3-carboxamida, N'-(2,5-dimethyl4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methylformamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihidroisoxazol5-yl]-3-chloro-phenyl]methanesulfonate, but-3-ynyl N-[6[[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate, methyla N-[[5Petição 870250055585, de 01 / 07 / 2025, pág. 106 / 501, 93 / 236 [4-(2,4-dimethylfenil)triazol-2-yl]-2-metilfenil]metil]carbamato, 3-cloro-6-metil-5-fenil-4-(2,4,6trifluorofenil)pyridazina, piridaclometila, 3(difluorometil)-1-metil-N-[1,1,3-trimetilindan-4yl]pyrazole-4-carboxamide, [2-[[1-(4-chlorofenil)pyrazol3-il]oximetil]-3-metil-fenil]-4-metil-tetrazol-5-ona, 1metil-4-[3-metil-2-[[2-metil-4-(3,4,5-trimetilpyrazol-1il)fenoxi]metil]fenil]tetrazol-5-ona, aminopyrifen, ametoctradin, amisulbrom, penflufen, (Z,2E)-5-[1-(4chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent3-enamide, florilpicoxamid, fenpicoxamid, tebufloquin, ipflufenoquin, quinofumelin, isofetamid, N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, benzothiostrobin, fenamacril, zinc salt 5-amino-1,3,4thiadiazole-2-thiol (2:1), fluopyram, flutianil, fluopimomide, pyrapropoina, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl1,1-dimethylindan-4-yl)pyridine-3-carboxamide, 2(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-, 3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyltetraprole, 2(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, a-(1,1-dimethylethyl)-α-[4'(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiproline, enoxastrobin, 4-[[6-[2-(2,4difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1yl)propyl]-3-pyridyl]oxy] benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4 Petition 870250055585, de 01 / 07 / 2025, p. 107 / 501 94 / 236 triazol-1-yl)propyl]-3-pyridyl]oxy] benzonitrile, 4-[[6-[2(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, coumoxystrobin, zhongshengmycin, copper thiodiazole, zinc thiazole, amectotractin, iprodione, N-octylN'-[2-(octylamino)ethyl]ethane-1,2-diamine, N'-[5-bromo-2methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-Nmethyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-Nethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-Nisopropyl-N-methyl-formamidine (these compounds can be prepared from the methods described in WO2015 / 155075);N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (these compounds can be prepared from the methods described in IPCOM000249876D); Nisopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxyethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the methods described in WO2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared from the methods described in WO2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-Petition 870250055585, dated 01 / 07 / 2025, page 108 / 501; 95 / 236 chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoroquinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3carboxamide, N-[(1S)-1-benzyl-1,3-dimethylbutyl]-7,8difluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[(3fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethylbutyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide, N[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methylbut-3-enyl)8-fluoroquinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methylbut-3-enyl)-8-fluoroquinoline-3-carboxamide (these compounds can be prepared from the methods described in WO2017 / 153380);1-(6,7-dimetilpirazolo[1,5-a]piridin-3yl)-4,4,5-trifluoro-3,3-dimetil-isoquinolina, 1-(6,7dimetilpirazolo[1,5-a]piridin-3-yl)-4,4,6-trifluoro-3,3dimetil-isoquinolina, 4,4-difluoro-3,3-dimetil-1-(6metilpirazolo[1,5-a]piridin-3-yl)isoquinolina, 4,4difluoro-3,3-dimetil-1-(7-metilpirazolo[1,5-a]piridin-3yl)isoquinolina, 1- (6-cloro-7-metil-pirazolo[1,5-a]piridin3-yl)-4,4-difluoro-3,3-dimetil-isoquinolina (estes compostis podem ser preparados a partir dos métodos descritos em WO2017 / 025510); 1-(4,5-dimetilbenzimidazol-1-yl)-4,4,5trifluoro-3,3-dimetil-isoquinolina, 1-(4,5dimetilbenzimidazol-1-yl)-4,4-difluoro-3,3-dimetilisoquinolina, 6-chloro-4,4-difluoro-3,3-dimetil-1-(4metilbenzimidazol-1-yl)isoquinolina, 4,4-difluoro-1-(5; Petition 870250055585, 01 / 07 / 2025, pág. 109 / 501 96 / 236 fluoro-4-metil-benzimidazol-1-yl)-3,3-dimethyl-isoquinolina, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-di-hidro-6Hciclopenta[e]benzimidazole (estes composdos podem ser preparados a partir dos métodos descritos em WO2016 / 156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3yl]phenyl]methyl]isoxazolidin-3-one,1-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (these compounds can be prepared from the methods described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 Petition 870250055585, dated 01 / 07 / 2025, page 110 / 501, 97 / 236 (1,2,4-triazol-1-yl)propan-2-ol (these compounds can be prepared using the methods described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (these compounds can be prepared using the methods described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (these compounds can be prepared using the methods described in WO 2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylate of (4-phenoxyphenyl)methyl (these compounds can be prepared from the methods described in WO 2014 / 006945); 2,6Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (these compounds can be prepared from the methods described in WO 2011 / 138281) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4-[5-(trifluoromethyl)1,2,4-oxadiazol-3-yl]benzamide;(Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide (these compounds can be prepared from the methods described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine (these compounds can be prepared from the methods described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (these compounds can be prepared from the methods described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these; Petition 870250055585, dated 01 / 07 / 2025, page 111 / 501 98 / 236 compounds can be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (these compounds can be prepared from the methods described in WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (these compounds can be prepared from the methods described in WO 2018 / 158365); 2,2-difluoro-N-methyl2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared from the methods described in WO 2018 / 202428).
[00132] The compounds of the invention can also be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from the class of macrocyclic lactone compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in EP-357460, EP-444964 and EP-594291. Additional anthelmintic agents include semi-synthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in US-5015630, WO-9415944 and WO-9522552. Additional anthelmintic agents include benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, Petition 870250055585, dated 01 / 07 / 2025, page 112 / 501 99 / 236 oxibendazole, parbendazole and other members of the class. Additional anthelmintic agents include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Additional anthelmintic agents include fluquicides, such as triclabendazole and clorsulone, and cestocides, such as praziquantel and epsiprantel.
[00133] The compounds of the invention can be used in combination with derivatives and analogues of the paraherquamide / marcfortine class of anthelmintic agents, as well as antiparasitic oxazolines, such as those disclosed in documents US-5478855, US-4639771 and DE-19520936.
[00134] The compounds of the invention can be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO-9615121 and also with active anthelmintic cyclic depsipeptides such as those described in WO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334, EP-382173 and EP-503538.
[00135] The compounds of the invention can be used in combination with other ectoparasiticides, for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenurone; ecdysone agonists such as tebufenozide and similar drugs; neonicotinoids such as imidacloprid and similar drugs.
[00136] The compounds of the invention can be used in combination with terpene alkaloids, for example those described in WO 95 / 19363 or WO 04 / 72086, particularly the compounds disclosed therein. Petition 870250055585, dated 01 / 07 / 2025, page 113 / 501 100 / 236
[00137] Other examples of such biologically active compounds with which the compounds of the invention may be used in combination include, but are not limited to, the following: Organophosphates: acephate, azamethifos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chloridexifos, chlorpyrifos, chlorfenvinfos, chlormefos, demeton, demeton-S-methyl, demeton-S-methylsulfone, dialifos, diazinon, dichlorvos, dicrotofos, dimethoate, disulfoton, ethion, etoprofos, etrimfos, famfur, fenamifos, fenitrothion, fensulfothion, fenthion, flupyrazofos, fonofos, formotion, fosthiazate, heptenofos, isazofos, isothioate, isoxation, malathion, methacryphos, methamidophos, metidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxidemeton-methyl, paraoxon, parathion, parathion-methyl, phentoate, phosalone, phospholane, phosphocarb, phosmet, phosfamidon, phorate, foxim, pirimiphos, pirimiphos-methyl, profenofos, propafos, proetamphos, protiophos, pyraclophos, pyridapenthion, quinalfos, sulprofos,temephos, terbufos, tebupirimphos, tetrachlorvinphos, timeton, triazophos, trichlorfon, vamidothion.,
[00138] Carbamates: alanicarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, chloretocarb, ethiofencarb, fenoxycarb, fenthiocarb, furatiocarb, HCN801, isoprocarb, indoxacarb, methiocarb, methomyl, 5methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, UC51717.
[00139] Pyrethroids: acrinatin, allethrin, alphamethrin, (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-) Petition 870250055585, dated 01 / 07 / 2025, page 114 / 501 101 / 236 5-benzyl-3furylmethyl ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, acypermethrin, beta-cypermethrin, bioalethrin, bioalethrin (isomer (S)-cyclopentyl), bioresmethrin, bifenthrin, NCI85193, cycloprothrin, cyhalothrin, cititrin, cifenothrin, deltamethrin, empentrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, phenothrin, pralethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, zetacypermethrin.
[00140] Arthropod growth regulators: a) chitin synthesis inhibitors: Benzoylureas: chlorfluazurone, diflubenzurone, fluazurone, flucicloxurone, flufenoxurone, hexaflumurone, lufenurone, novalurone, teflubenzurone, triflumurone, buprofezin, diphenol, hexithiazox, ethoxazole, chlorfentazine; b) Ecdysone antagonists: halofenozide, methoxyfenozide, tebufenozide; c) Juvenoids: pyriproxyfen, methoprene (including S-methoprene), phenoxycarb; d) Lipid biosynthesis inhibitors: spirodiclofen.
[00141] Other antiparasitics: acequinocil, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus turingiensis, bensultape, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, campechlor, cartape, chlorobenzylate, chlordimeform, chlorfenapyr, chromafenozide, clothianidin, cyromazine, diaclodene, diafentiurone, DBI3204, dynactin, dihydroxymethyldihydroxypyrrolidine, Petition 870250055585, dated 01 / 07 / 2025, page 115 / 501 102 / 236 dinobutone, dinocape, endosulfan, etiprol, etofenprox, fenazaquine, flumite, MTI-800, fenpyroximate, fluacripyrime, flubenzimine, flubrocitrinate, flufenzine, flufenprox, fluproxifen, halofenprox, hydramethylnone, IKI-220, canemite, NC-196, protective neem, nidinorterfuran, nitanpyram, SD-35651, WL-108477, pyridaryl, propargite, protrifenbut, pymetrozine, pyridabem, pyrimidifem, NC1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI8601, silafluofen, silomadine, spinosad, tebufenpyrad, tetradiphone, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosin, trinactin, verbutin, vertalec, YI-5301.
[00142] Biological agents: Delta endotoxin of Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis, baculovirus, entomopathogenic bacteria, viruses and fungi.
[00143] Bactericides: chlortetracycline, oxytetracycline, streptomycin.
[00144] Other biological agents: enrofloxacin, febantel, penetamate, moloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, piriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel, triclabendazole.
[00145] Another aspect of the invention relates to the use of a compound of formula (I) or of a preferred individual compound as defined above, of a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, or of a fungicidal or insecticidal mixture. Petition 870250055585, dated 01 / 07 / 2025, page 116 / 501 103 / 236 comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, in a mixture with addition with other fungicides or insecticides as described above, for the control or prevention of infestation of plants, for example, useful plants such as crop plants, their propagation material, for example, seeds, harvested crops, for example, harvested food crops, or non-living materials by insects or by phytopathogenic microorganisms, preferably fungal organisms.
[00146] A further aspect of the invention relates to a method of controlling or preventing an infestation of plants, for example, useful plants such as crop plants, their propagation material, for example, seeds, harvested crops, for example, harvested food crops, or non-living materials by insects or by microorganisms or phytopathogenic organisms that cause deterioration potentially harmful to humans, especially fungal organisms, comprising applying a compound of formula (I) or a preferred individual compound as defined above as the active ingredient to the plants, parts of the plants or their locus, their propagation material or any part of the non-living materials.
[00147] Control or prevention means reducing infestation by insects or by phytopathogenic microorganisms or those that cause deterioration or organisms that are potentially harmful to humans, especially fungal organisms, to a level where an improvement is demonstrated. Petition 870250055585, dated 01 / 07 / 2025, page 117 / 501 104 / 236
[00148] A preferred method of controlling or preventing infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects, comprising the application of a compound of formula (I), or an agrochemical composition containing at least one of said compounds, is foliar application. The frequency of application and the application rate will depend on the risk of infestation by the corresponding pathogen or insect. However, compounds of formula (I) can also penetrate the plant through the roots via the soil (systemic action), by soaking the plant locus with a liquid formulation, or by applying the compounds in solid form to the soil, for example, in granular form (soil application). In irrigated rice crops, these granules can be applied to the irrigated rice field.The compounds of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or coating them with a solid formulation.
[00149] A formulation, for example a composition containing the compound of formula (I) and, if desired, a solid or liquid adjuvant or monomers for encapsulation of the compound of formula (I) can be prepared in a known manner, typically by intimate mixing and / or trituration of the compound with diluents, for example solvents, solid carriers and, optionally, surface-active compounds (surfactants).
[00150] Advantageous application rates typically range from 5 ga (2 kg of active ingredient) per hectare (ha), preferably from 10 ga (1 kg of active ingredient / ha), Petition 870250055585, dated 01 / 07 / 2025, p. 118 / 501 105 / 236 more preferably 20 g to 600 g of active ingredient / ha. When used as a seed soaking agent, suitable dosages are 10 mg to 1 g of active substance per kg of seeds.
[00151] When the combinations of the present invention are used for seed treatment, rates of 0.001 to 50 g of a compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, are generally sufficient.
[00152] The compositions of the invention can be employed in any conventional form, for example in the form of a double package, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a flowable seed treatment concentrate (FS), a seed treatment solution (LS), a water-dispersible seed treatment powder (WS), a seed treatment capsule suspension (CF), a seed treatment gel (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG), a water-in-oil emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), a liquid of volume ultra-low (UL), a technical concentrate (TK),a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants. Petition 870250055585, dated 01 / 07 / 2025, page 119 / 501 106 / 236
[00153] Such compositions can be produced conventionally, e.g., by mixing the active ingredients with appropriate inert formulation substances (diluents, solvents, fillers and optionally other formulation ingredients such as surfactants, biocides, antifreeze, adhesives, thickeners and compounds that provide adjuvant effects). Conventional slow-release formulations can also be used when long-lasting efficacy is desired.In particular, formulations to be applied in spray forms, such as water-dispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like), wettable powders and granules, may contain surfactants such as wetting and dispersing agents, and other compounds that provide adjuvant effects, for example the condensation product of formaldehyde with naphthalenesulfonate, an alkylarylsulfonate, a lignin sulfonate, an ethoxylated fatty alkyl sulfate and alkylphenol, and an ethoxylated fatty alcohol.
[00154] A seed-curing formulation is applied in a manner known per se to seeds using the combination of the invention and a diluent in the form of a formulation suitable for seed curing, for example, as an aqueous suspension or in the form of a dry powder with good adherence to the seeds. Such seed-coating formulations are known in the art. Seed-curing formulations may contain the single active ingredients or a combination of active ingredients in encapsulated form, for example, as slow-release capsules or microcapsules.
[00155] In general, formulations include 0.01 to 90% by weight of active agent, and 0 to 20% surfactant. Petition 870250055585, dated 01 / 07 / 2025, page 120 / 501 107 / 236 agriculturally acceptable and 10 to 99.99% of solid or liquid formulation inerts and adjuvant(s), the active agent consisting at least of the compound of formula (I) together with components (B) and (C) and, optionally, other active agents, particularly microbiocides or preservatives or similar. Concentrated forms of compositions generally contain between about 2 and 80%, preferably between about 5 and 70% by weight of active agent. Application forms of the formulation may contain, for example, from 0.01 to 20% by weight, preferably from 0.01 to 5% by weight of active agent. Although commercial products are preferably formulated as concentrates, the end user will normally employ diluted formulations.
[00156] Table 1 below illustrates examples of individual compounds of formula (I) according to the invention.
[00157] Table A-1 provides 91 compounds A-1.001 to A-1.091 of formula (Ia) R3ORk JJ / r4ilN(Ia) where A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is phenyl, and R2 and R3 are as defined in Table 1. Table 1: Individual compounds of formula (I) according to the invention Petition 870250055585, dated 01 / 07 / 2025, p. 121 / 501 108 / 236 No. Compound R2 R3 Comp. No. R2 R3 Comp. No. R2 R3 001 HH 032 Cl och3 063 F och2ch= ch2 002 H ch3 033 Cl och2ch3 064 F OCHF2 003 HF 034 Cl 0- cyclop ropil 065 F ocf3 004 H Cl 035 Cl OCH(CH 3) 2 066 och3 H 005 H Br 036 Cl OCH2CC H 067 och3 ch3 006 H och3 037 Cl OCH2CH =ch2 068 och3 F 007 H och2 ch3 038 Cl OCHF2 069 och3 Cl 008 H O- cycle opro pila 039 Cl ocf3 070 och3 Br 009 H OCH ( CH3)2 040 Br H 071 och3 och3 010 H och2 CCH 041 Br ch3 072 och3 och2ch3 Oil H och2 CH=C h2 042 Br F 073 och3 0ciclopr opila 012 H OCHF 2 043 Br Cl 074 och3 OCH (CH3 ) 2 Petition 870250055585, dated 01 / 07 / 2025, p. 122 / 501 109 / 236 No. Composite R2 R3 Comp. N° R2 R3 Comp. N° R2 R3 013 H ocf3 044 Br Br 075 och3 och2cch 014 ch3 H 045 Br och3 076 och3 och2ch= ch2 015 ch3 ch3 046 Br och2ch3 077 och3 ochf2 016 ch3 F 047 Br 0- ciclop ropila 078 och3 ocf3 017 ch3 Cl 048 Br OCH(CH 3) 2 079 och2c h3 H 018 ch3 Br 049 Br och2cc H 080 och2c h3 ch3 019 ch3 och3 050 Br och2ch =ch2 081 och2c h3 F 020 ch3 och2 ch3 051 Br ochf2 082 och2c h3 Cl 021 ch3 0- cicl opro pila 052 Br ocf3 083 och2c h3 Br 022 ch3 OCH ( CH3)2 053 F H 084 och2c h3 och3 023 ch3 och2 CCH 054 F ch3 085 och2c h3 och2ch3 024 ch3 och2 CH=C h2 055 FF 086 och2c h3 0ciclopr opila Petition: 870250055585, on 01 / 07 / 2025, page. 123 / 501 110 / 236 No. Comp sto R2 R3 Comp. No. R2 R3 Comp. No. R2 R3 025 ch3 OCHF 2 056 F Cl 087 OCH2C h3 OCH (CH3 ) 2 026 ch3 ocf3 057 F Br 088 OCH2C h3 OCH2CCH 027 Cl H 058 F och3 089 OCH2C h3 OCH2CH= ch2 028 Cl ch3 059 F och2ch3 090 OCH2C h3 OCHF2 029 Cl F 060 F 0- cyclop ropila 091 OCH2C h3 ocf3 030 Cl Cl 061 F OCH(CH 3) 2 031 Cl Br 062 F OCH2CC H
[00158] Table A-2 provides 91 compounds A-2.001 and A-2.091 of formula (Ia) where A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00159] Table A-3 provides 91 compounds A-3.001 to A-3.091 of formula (Ia) where A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00160] Table A-4 provides 91 compounds A-4.001 and A-4.091 of formula (Ia) where A is CH, R4 is (2,2 Petition 870250055585, dated 01 / 07 / 2025, page 124 / 501 111 / 236 dimethylcyclobutyl), R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00161] Table A-5 provides 91 compounds A-5.001 and A-5.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00162] Table A-6 provides 91 compounds A-6.001 to A-6.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 3-methylphenyl, and R2 and R3 are as defined in Table 1.
[00163] Table A-7 provides 91 compounds A-7.001 to A-7.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 3,5-dimethylphenyl, and R2 and R3 are as defined in Table 1.
[00164] Table A-8 provides 91 compounds A-8.001 to A-8.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00165] Table A-9 provides 91 compounds A-9.001 to A-9.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00166] Table A-10 provides 91 compounds A10.001 to A-10.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00167] Table A-11 provides 91 compounds A11.001 to A-11.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 125 / 501 112 / 236
[00168] Table A-12 provides 91 compounds A12.001 to A-12.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 2,6-difluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00169] Table A-13 provides 91 compounds A13.001 to A-13.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00170] Table A-14 provides 91 compounds A14.001 to A-14.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 2,6-dichloropyridine-4-yl and R2 and R3 are as defined in Table 1.
[00171] Table A-15 provides 91 compounds A15.001 to A-15.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00172] Table A-16 provides 91 compounds A16.001 to A-16.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 6-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00173] Table A-17 provides 91 compounds A17.001 to A-17.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 5-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00174] Table A-18 provides 91 compounds A18.001 to A-18.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00175] Table A-19 provides 91 compounds A19.001 to A-19.091 of formula (Ia) wherein A is CH, R4 is (2,2 Petition 870250055585, dated 01 / 07 / 2025, page 126 / 501 113 / 236 dimethylcyclobutyl), R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00176] Table A-20 provides 91 compounds A20.001 to A-20.091 of formula (Ia) wherein A is CH, R4 is (2,2-dimethylcyclobutyl), R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00177] Table A-21 provides 91 compounds A21.001 to A-21.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is phenyl, and R2 and R3 are as defined in Table 1.
[00178] Table A-22 provides 91 compounds A22.001 to A-22.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00179] Table A-23 provides 91 compounds A23.001 to A-23.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00180] Table A-24 provides 91 compounds A24.001 to A-24.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00181] Table A-25 provides 91 compounds A25.001 to A-25.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00182] Table A-26 provides 91 compounds A26.001 to A-26.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 127 / 501 114 / 236
[00183] Table A-27 provides 91 compounds A27.001 to A-27.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 3,5-dimethylphenyl and R2 and R3 are as defined in Table 1.
[00184] Table A-28 provides 91 compounds A28.001 to A-28.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00185] Table A-29 provides 91 compounds A29.001 to A-29.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00186] Table A-30 provides 91 compounds A30.001 to A-30.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00187] Table A-31 provides 91 compounds A31.001 to A-31.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00188] Table A-32 provides 91 compounds A32.001 to A-32.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 2,6-difluoropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00189] Table A-33 provides 91 compounds A33.001 to A-33.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00190] Table A-34 provides 91 compounds A34.001 to A-34.091 of formula (Ia) wherein A is CH, R4 is tert Petition 870250055585, dated 01 / 07 / 2025, page 128 / 501 115 / 236 butyl, R5 is 2,6-dichloropyridine-4-yl and R2 and R3 are as defined in Table 1.
[00191] Table A-35 provides 91 compounds A35.001 to A-35.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00192] Table A-36 provides 91 compounds A36.001 to A-36.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 6-fluoropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00193] Table A-37 provides 91 compounds A37.001 to A-37.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 5-fluoropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00194] Table A-38 provides 91 compounds A38.001 to A-38.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00195] Table A-39 provides 91 compounds A39.001 to A-39.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00196] Table A-40 provides 91 compounds A40.001 to A-40.091 of formula (Ia) wherein A is CH, R4 is tert-butyl, R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00197] Table A-41 provides 91 compounds A41.001 to A-41.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is phenyl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 129 / 501 116 / 236
[00198] Table A-42 provides 91 compounds A42.001 to A-42.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00199] Table A-43 provides 91 compounds A43.001 to A-43.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00200] Table A-44 provides 91 compounds A44.001 to A-44.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00201] Table A-45 provides 91 compounds A45.001 to A-45.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00202] Table A-46 provides 91 compounds A46.001 to A-46.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1.
[00203] Table A-47 provides 91 compounds A47.001 to A-47.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 3,5-dimethylphenyl and R2 and R3 are as defined in Table 1.
[00204] Table A-48 provides 91 compounds A48.001 to A-48.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00205] Table A-49 provides 91 compounds A49.001 to A-49.091 of formula (Ia) wherein A is CH, R4 is (1Petition 870250055585, dated 01 / 07 / 2025, page 130 / 501 117 / 236 methylcyclopropyl), R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00206] Table A-50 provides 91 compounds A50.001 to A-50.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00207] Table A-51 provides 91 compounds A51.001 to A-51.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00208] Table A-52 provides 91 compounds A52.001 to A-52.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 2,6-difluoropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00209] Table A-53 provides 91 compounds A53.001 to A-53.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00210] Table A-54 provides 91 compounds A54.001 to A-54.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 2,6-dichloropyridine-4-yl and R2 and R3 are as defined in Table 1.
[00211] Table A-55 provides 91 compounds A55.001 to A-55.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00212] Table A-56 provides 91 compounds A56.001 to A-56.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 6-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 131 / 501 118 / 236
[00213] Table A-57 provides 91 compounds A57.001 to A-57.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 5-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00214] Table A-58 provides 91 compounds A58.001 to A-58.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00215] Table A-59 provides 91 compounds A59.001 to A-59.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00216] Table A-60 provides 91 compounds A60.001 to A-60.091 of formula (Ia) wherein A is CH, R4 is (1-methylcyclopropyl), R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00217] Table A-61 provides 91 compounds A61.001 to A-61.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is phenyl, and R2 and R3 are as defined in Table 1.
[00218] Table A-62 provides 91 compounds A62.001 to A-62.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00219] Table A-63 provides 91 compounds A63.001 to A-63.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00220] Table A-64 provides 91 compounds A64.001 to A-64.091 of formula (Ia) wherein A is CH, R4 is 2,2 Petition 870250055585, dated 01 / 07 / 2025, page 132 / 501 119 / 236 dimethylpropyl, R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00221] Table A-65 provides 91 compounds A65.001 to A-65.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00222] Table A-66 provides 91 compounds A66.001 to A-66.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1.
[00223] Table A-67 provides 91 compounds A67.001 to A-67.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 3,5-dimethylphenyl and R2 and R3 are as defined in Table 1.
[00224] Table A-68 provides 91 compounds A68.001 to A-68.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00225] Table A-69 provides 91 compounds A69.001 to A-69.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00226] Table A-70 provides 91 compounds A70.001 to A-70.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00227] Table A-71 provides 91 compounds A71.001 to A-71.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 133 / 501 120 / 236
[00228] Table A-72 provides 91 compounds A72.001 to A-72.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 2,6-difluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00229] Table A-73 provides 91 compounds A73.001 to A-73.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00230] Table A-74 provides 91 compounds A74.001 to A-74.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 2,6-dichloropyridine-4-yl and R2 and R3 are as defined in Table 1.
[00231] Table A-75 provides 91 compounds A75.001 to A-75.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00232] Table A-76 provides 91 compounds A76.001 to A-76.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 6-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00233] Table A-77 provides 91 compounds A77.001 to A-77.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 5-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00234] Table A-78 provides 91 compounds A78.001 to A-78.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00235] Table A-79 provides 91 compounds A79.001 to A-79.091 of formula (Ia) wherein A is CH, R4 is 2,2 Petition 870250055585, dated 01 / 07 / 2025, page 134 / 501 121 / 236 dimethylpropyl, R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00236] Table A-80 provides 91 compounds A80.001 to A-80.091 of formula (Ia) wherein A is CH, R4 is 2,2-dimethylpropyl, R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00237] Table A-81 provides 91 compounds A81.001 to A-81.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is phenyl, and R2 and R3 are as defined in Table 1.
[00238] Table A-82 provides 91 compounds A82.001 to A-82.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00239] Table A-83 provides 91 compounds A83.001 to A-83.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00240] Table A-84 provides 91 compounds A84.001 to A-84.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00241] Table A-85 provides 91 compounds A85.001 to A-85.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00242] Table A-86 provides 91 compounds A86.001 to A-86.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 135 / 501 122 / 236
[00243] Table A-87 provides 91 compounds A87.001 to A-87.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 3,5-dimethylphenyl and R2 and R3 are as defined in Table 1.
[00244] Table A-88 provides 91 compounds A88.001 to A-88.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00245] Table A-89 provides 91 compounds A89.001 to A-89.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00246] Table A-90 provides 91 compounds A90.001 to A-90.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00247] Table A-91 provides 91 compounds A91.001 to A-91.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00248] Table A-92 provides 91 compounds A92.001 to A-92.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 2,6-difluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00249] Table A-93 provides 91 compounds A93.001 to A-93.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00250] Table A-94 provides 91 compounds A94.001 to A-94.091 of formula (Ia) wherein A is CH, R4 is Petition 870250055585, dated 01 / 07 / 2025, page 136 / 501 123 / 236 isopentyl, R5 is 2,6-difluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00251] Table A-95 provides 91 compounds A95.001 to A-95.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00252] Table A-96 provides 91 compounds A96.001 to A-96.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 6-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00253] Table A-97 provides 91 compounds A97.001 to A-97.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 5-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00254] Table A-98 provides 91 compounds A98.001 to A-98.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00255] Table A-99 provides 91 compounds A99.001 to A-99.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00256] Table A-100 provides 91 compounds A100.001 to A-100.091 of formula (Ia) wherein A is CH, R4 is isopentyl, R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00257] Table A-101 provides 91 compounds A101.001 to A-101.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is phenyl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 137 / 501 124 / 236
[00258] Table A-102 provides 91 compounds A102.001 to A-102.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00259] Table A-103 provides 91 compounds A103.001 to A-103.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00260] Table A-104 provides 91 compounds A104.001 to A-104.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00261] Table A-105 provides 91 compounds A105.001 to A-105.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00262] Table A-106 provides 91 compounds A106.001 to A-106.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1.
[00263] Table A-107 provides 91 compounds A107.001 to A-107.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 3,5-dimethylphenyl, and R2 and R3 are as defined in Table 1.
[00264] Table A-108 provides 91 compounds A108.001 to A-108.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00265] Table A-109 provides 91 compounds A109.001 to A-109.091 of formula (Ia) wherein A is N, R4 is (2,2 Petition 870250055585, dated 01 / 07 / 2025, page 138 / 501 125 / 236 dimethylcyclobutyl), R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00266] Table A-110 provides 91 compounds A110.001 to A-110.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00267] Table A-111 provides 91 compounds A111.001 to A-111.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00268] Table A-112 provides 91 compounds A112.001 to A-112.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 2,6-difluoropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00269] Table A-113 provides 91 compounds A113.001 to A-113.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00270] Table A-114 provides 91 compounds A114.001 to A-114.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 2,6-dichloropyridine-4-yl and R2 and R3 are as defined in Table 1.
[00271] Table A-115 provides 91 compounds A115.001 to A-115.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00272] Table A-116 provides 91 compounds A116.001 to A-116.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 6-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 139 / 501 126 / 236
[00273] Table A-117 provides 91 compounds A117.001 to A-117.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 5-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00274] Table A-118 provides 91 compounds A118.001 to A-118.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00275] Table A-119 provides 91 compounds A119.001 to A-119.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00276] Table A-120 provides 91 compounds A120.001 to A-120.091 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl), R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00277] Table A-121 provides 91 compounds A121.001 to A-121.091 of formula (Ia) wherein A is N, R4 is tert-butyl, R5 is phenyl, and R2 and R3 are as defined in Table 1.
[00278] Table A-122 provides 91 compounds A122.001 to A-122.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00279] Table A-123 provides 91 compounds A123.001 to A-123.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00280] Table A-124 provides 91 compounds A124.001 to A-124.091 of formula (Ia) where A is N, R4 is tert-124. Petition 870250055585, dated 01 / 07 / 2025, p. 140 / 501 127 / 236 butyl, R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00281] Table A-125 provides 91 compounds A125.001 to A-125.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00282] Table A-126 provides 91 compounds A126.001 to A-126.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1.
[00283] Table A-127 provides 91 compounds A127.001 to A-127.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 3,5-dimethylphenyl and R2 and R3 are as defined in Table 1.
[00284] Table A-128 provides 91 compounds A128.001 to A-128.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00285] Table A-129 provides 91 compounds A129.001 to A-129.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00286] Table A-130 provides 91 compounds A130.001 to A-130.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00287] Table A-131 provides 91 compounds A131.001 to A-131.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, p. 141 / 501 128 / 236
[00288] Table A-132 provides 91 compounds A132.001 to A-132.091 of formula (Ia) wherein A is N, R4 is tert-butyl, R5 is 2,6-difluoropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00289] Table A-133 provides 91 compounds A133.001 to A-133.091 of formula (Ia) wherein A is N, R4 is tert-butyl, R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00290] Table A-134 provides 91 compounds A134.001 to A-134.091 of formula (Ia) wherein A is N, R4 is tert-butyl, R5 is 2,6-dichloropyridine-4-yl and R2 and R3 are as defined in Table 1.
[00291] Table A-135 provides 91 compounds A135.001 to A-135.091 of formula (Ia) wherein A is N, R4 is tert-butyl, R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00292] Table A-136 provides 91 compounds A136.001 to A-136.091 of formula (Ia) wherein A is N, R4 is tert-butyl, R5 is 6-fluoropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00293] Table A-137 provides 91 compounds A137.001 to A-137.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 5-fluoropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00294] Table A-138 provides 91 compounds A138.001 to A-138.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00295] Table A-139 provides 91 compounds A139.001 to A-139.091 of formula (Ia) where A is N, R4 is tert Petition 870250055585, dated 01 / 07 / 2025, p. 142 / 501 129 / 236 butyl, R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00296] Table A-140 provides 91 compounds A140.001 to A-140.091 of formula (Ia) where A is N, R4 is tert-butyl, R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00297] Table A-141 provides 91 compounds A141.001 to A-141.091 of formula (Ia) where A is N, R4 is (1-methylcyclopropyl), R5 is phenyl, and R2 and R3 are as defined in Table 1.
[00298] Table A-142 provides 91 compounds A142.001 to A-142.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00299] Table A-143 provides 91 compounds A143.001 to A-143.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00300] Table A-144 provides 91 compounds A144.001 to A-144.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00301] Table A-145 provides 91 compounds A145.001 to A-145.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00302] Table A-146 provides 91 compounds A146.001 to A-146.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 143 / 501 130 / 236
[00303] Table A-147 provides 91 compounds A147.001 to A-147.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 3,5-dimethylphenyl and R2 and R3 are as defined in Table 1.
[00304] Table A-148 provides 91 compounds A148.001 to A-148.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00305] Table A-149 provides 91 compounds A149.001 to A-149.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00306] Table A-150 provides 91 compounds A150.001 to A-150.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00307] Table A-151 provides 91 compounds A151.001 to A-151.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00308] Table A-152 provides 91 compounds A152.001 to A-152.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 2,6-difluoropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00309] Table A-153 provides 91 compounds A153.001 to A-153.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00310] Table A-154 provides 91 compounds A154.001 to A-154.091 of formula (Ia) wherein A is N, R4 is (1 Petition 870250055585, dated 01 / 07 / 2025, page 144 / 501 131 / 236 methylcyclopropyl), R5 is 2,6-dichloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00311] Table A-155 provides 91 compounds A155.001 to A-155.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00312] Table A-156 provides 91 compounds A156.001 to A-156.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 2-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00313] Table A-157 provides 91 compounds A157.001 to A-157.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 5-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00314] Table A-158 provides 91 compounds A158.001 to A-158.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00315] Table A-159 provides 91 compounds A159.001 to A-159.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00316] Table A-160 provides 91 compounds A160.001 to A-160.091 of formula (Ia) wherein A is N, R4 is (1-methylcyclopropyl), R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00317] Table A-161 provides 91 compounds A161.001 to A-161.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is phenyl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 145 / 501 132 / 236
[00318] Table A-162 provides 91 compounds A162.001 to A-162.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00319] Table A-163 provides 91 compounds A163.001 to A-163.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00320] Table A-164 provides 91 compounds A164.001 to A-164.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00321] Table A-165 provides 91 compounds A165.001 to A-165.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00322] Table A-166 provides 91 compounds A166.001 to A-166.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1.
[00323] Table A-167 provides 91 compounds A167.001 to A-167.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 3,5-dimethylphenyl and R2 and R3 are as defined in Table 1.
[00324] Table A-168 provides 91 compounds A168.001 to A-168.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00325] Table A-169 provides 91 compounds A169.001 to A-169.091 of formula (Ia) wherein A is N, R4 is 2,2 Petition 870250055585, dated 01 / 07 / 2025, page 146 / 501 133 / 236 dimethylpropyl, R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00326] Table A-170 provides 91 compounds A170.001 to A-170.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00327] Table A-171 provides 91 compounds A171.001 to A-171.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00328] Table A-172 provides 91 compounds A172.001 to A-172.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 2,6-difluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00329] Table A-173 provides 91 compounds A173.001 to A-173.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00330] Table A-174 provides 91 compounds A174.001 to A-174.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 2,6-dichloropyridine-4-yl and R2 and R3 are as defined in Table 1.
[00331] Table A-175 provides 91 compounds A175.001 to A-175.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00332] Table A-176 provides 91 compounds A176.001 to A-176.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 6-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 147 / 501 134 / 236
[00333] Table A-177 provides 91 compounds A177.001 to A-177.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 5-fluoropyridin-3-yl, and R2 and R3 are as defined in Table 1.
[00334] Table A-178 provides 91 compounds A178.001 to A-178.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00335] Table A-179 provides 91 compounds A179.001 to A-179.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00336] Table A-180 provides 91 compounds A180.001 to A-180.091 of formula (Ia) wherein A is N, R4 is 2,2-dimethylpropyl, R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00337] Table A-181 provides 91 compounds A181.001 to A-181.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is phenyl, and R2 and R3 are as defined in Table 1.
[00338] Table A-182 provides 91 compounds A182.001 to A-182.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 3-fluorophenyl and R2 and R3 are as defined in Table 1.
[00339] Table A-183 provides 91 compounds A183.001 to A-183.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 3,5-difluorophenyl and R2 and R3 are as defined in Table 1.
[00340] Table A-184 provides 91 compounds A184.001 to A-184.091 of formula (Ia) wherein A is N, R4 is Petition 870250055585, dated 01 / 07 / 2025, page 148 / 501 135 / 236 isopentyl, R5 is 3-chlorophenyl and R2 and R3 are as defined in Table 1.
[00341] Table A-185 provides 91 compounds A185.001 to A-185.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 3,5-dichlorophenyl and R2 and R3 are as defined in Table 1.
[00342] Table A-186 provides 91 compounds A186.001 to A-186.091 of formula (Ia) wherein A is N, R4 isopentyl, R5 is 3-methylphenyl and R2 and R3 are as defined in Table 1.
[00343] Table A-187 provides 91 compounds A187.001 to A-187.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 3,5-dimethylphenyl and R2 and R3 are as defined in Table 1.
[00344] Table A-188 provides 91 compounds A188.001 to A-188.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 3-methoxyphenyl and R2 and R3 are as defined in Table 1.
[00345] Table A-189 provides 91 compounds A189.001 to A-189.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 3,5-dimethoxyphenyl and R2 and R3 are as defined in Table 1.
[00346] Table A-190 provides 91 compounds A190.001 to A-190.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is pyridin-4-yl and R2 and R3 are as defined in Table 1.
[00347] Table A-191 provides 91 compounds A191.001 to A-191.091 of formula (Ia) wherein A is N, R4 is sopentyl, R5 is 2-fluoropyridin-4-yl, and R2 and R3 are as defined in Table 1. Petition 870250055585, dated 01 / 07 / 2025, page 149 / 501 136 / 236
[00348] Table A-192 provides 91 compounds A192.001 to A-192.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 2,6-difluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00349] Table A-193 provides 91 compounds A193.001 to A-193.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 2-chloropyridin-4-yl and R2 and R3 are as defined in Table 1.
[00350] Table A-194 provides 91 compounds A194.001 to A-194.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 2,6-difluoropyridin-4-yl, and R2 and R3 are as defined in Table 1.
[00351] Table A-195 provides 91 compounds A195.001 to A-195.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is pyridin-3-yl and R2 and R3 are as defined in Table 1.
[00352] Table A-196 provides 91 compounds A196.001 to A-196.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 6-fluoropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00353] Table A-197 provides 91 compounds A197.001 to A-197.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 5-fluoropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00354] Table A-198 provides 91 compounds A198.001 to A-198.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is 6-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00355] Table A-199 provides 91 compounds A199.001 to A-199.091 of formula (Ia) wherein A is N, R4 is Petition 870250055585, dated 01 / 07 / 2025, pages 150 / 501 137 / 236 isopentyl, R5 is 5-chloropyridin-3-yl and R2 and R3 are as defined in Table 1.
[00356] Table A-200 provides 91 compounds A200.001 to A-200.091 of formula (Ia) wherein A is N, R4 is isopentyl, R5 is isothiazole-4-yl and R2 and R3 are as defined in Table 1.
[00357] Table B1 provides 36 compounds B-1.001 to B1.036 of formula (Ib) (Ib) where A is CH, R4 is (2,2-dimethylcyclobutyl) and R1, R2, R3, and R5 are as defined in Table 2. Table 2: Individual compounds of formula (I) according to the invention No. Compound R1 R2 R3 R5 001 CN HH 3,5-difluorophenyl 002 CN HH 2,6-difluoropyridin-4-yl 003 CN H och3 3,5-difluorophenyl 004 CN H och3 2,6-difluoropyridin-4-yl 005 CN H och2ch3 3,5-difluorophenyl 006 CN H och2ch3 2,6-difluoropyridin- 4-yl 007 CN och3 H 3,5-difluorophenyl Petition 870250055585, dated 01 / 07 / 2025, p. 151 / 501 138 / 236 Well Comp osto R1 R2 R3 R5 008 CN OCH3 H 2,6-difluoropyridin-4-yl 009 CN OCH3 OCH3 3,5-difluorophenyl 010 CN OCH3 OCH3 2,6-difluoropyridin-4-yl Oil CN OCH3 OCH2CH3 3,5-difluorophenyl 012 CN OCH3 OCH2CH3 2,6-difluoropyridin-4-yl 013 CN OCH2CH3 H 3,5-difluorophenyl 014 CN OCH2CH3 H 2,6-difluoropyridin-4-yl 015 CN OCH2CH3 OCH3 3,5-difluorophenyl 016 CN OCH2CH3 OCH3 2,6-difluoropyridin-4-yl 017 CN OCH2CH3 OCH2CH3 3,5-difluorophenyl 018 CN OCH2CH3 OCH2CH3 2,6-difluoropyridin-4-yl 019 COCH3 HH 3,5-difluorophenyl 020 COCH3 HH 2,6-difluoropyridin-4-yl 021 COCH3 H OCH3 3,5-difluorophenyl 022 COCH3 H OCH3 2,6-difluoropyridin-4-yl 023 COCH3 H OCH2CH3 3,5-difluorophenyl 024 COCH3 H OCH2CH3 2,6-difluoropyridin-4-yl 025 COCH3 OCH3 H 3,5-difluorophenyl Petition 870250055585, de 01 / 07 / 2025, pag. 152 / 501 139 / 236 Compound No. R1 R2 R3 R5 026 COCH3 OCH3 H 2,6-difluoropyridin-4-yl 027 COCH3 OCH3 OCH3 3,5-difluorophenyl 028 COCH3 OCH3 OCH3 2,6-difluoropyridin-4-yl 029 COCH3 OCH3 OCH2CH3 3,5-difluorophenyl 030 COCH3 OCH3 OCH2CH3 2,6-difluoropyridin- 4-yl 031 COCH3 OCH2CH3 H 3,5-difluorophenyl 032 COCH3 OCH2CH3 H 2,6-difluoropyridin- 4-yl 033 COCH3 OCH2CH3 OCH3 3,5-difluorophenyl 034 COCH3 OCH2CH3 OCH3 2,6-difluoropyridin- 4-yl 035 COCH3 OCH2CH3 OCH2CH3 3,5-difluorophenyl 036 COCH3 OCH2CH3 OCH2CH3 2,6-difluoropyridin- 4-yl
[00358] Table B-2 provides 36 compounds B-2.001 to B-2.036 of formula (Ib) wherein A is CH, R4 is tert-butyl and R1, R2, R3, and R5 are as defined in Table 2.
[00359] Table B-3 provides 36 compounds B-3.001 to B-3.036 of formula (Ia) wherein A is CH, R4 is (1-dimethylcyclopropyl) and R1, R2, R3, and R5 are as defined in Table 2.
[00360] Table B-4 provides 36 compounds B-4.001 to B-4.036 of formula (Ib) wherein A is CH, R4 is 2,2 Petition 870250055585, dated 01 / 07 / 2025, page 153 / 501 140 / 236 dimethylpropyl and R1, R2, R3, and R5 are as defined in Table 2.
[00361] Table B-5 provides 36 compounds B-5.001 to B-5.036 of formula (Ib) wherein A is CH, R4 is isopentyl and R1, R2, R3, and R5 are as defined in Table 2.
[00362] Table B-6 provides 36 compounds B-6.001 to B-6.036 of formula (Ia) wherein A is N, R4 is (2,2-dimethylcyclobutyl) and R1, R2, R3, and R5 are as defined in Table 2.
[00363] Table B-7 provides 36 compounds B-7.001 to B-7.036 of formula (Ib) wherein A is N, R4 is tert-butyl and R1, R2, R3, and R5 are as defined in Table 2.
[00364] Table B-8 provides 36 compounds B-8.001 to B-8.036 of formula (Ia) wherein A is N, R4 is (1-dimethylcyclopropyl) and R1, R2, R3, and R5 are as defined in Table 2.
[00365] Table B-9 provides 36 compounds B-9.001 to B-9.036 of formula (Ib) wherein A is N, R4 is 2,2-dimethylpropyl and R1, R2, R3, and R5 are as defined in Table 2.
[00366] Table B-10 provides 36 compounds B10.001 to B-10.036 of formula (Ib) wherein A is N, R4 is isopentyl and R1, R2, R3, and R5 are as defined in Table 2. Formulation Examples Post-wetting agents a) b) c) active ingredient [compound formula (I)] 25% 50% 75% sodium lignosulfonate 5% 5% - sodium lauryl sulfate 3% - 5% Petition 870250055585, dated 01 / 07 / 2025, page 154 / 501 141 / 236 diisobutylnaphthalenesulfonate - 6% 10% sodium polyethylene glycol ether phenol - 2% (7-8 mol ethylene oxide) highly dispersed silicic acid 5% 10% 10% Kaolin 62% 27%
[00367] The active ingredient is extensively mixed with the adjuvants and the mixture is extensively ground in a suitable mill, resulting in wettable powders that can be diluted with water to give suspensions of the desired concentration. Powders for seed treatment aa) b) c) dry active ingredient formula (I)] light mineral oil [composed of 25% 50% 75% highly dispersed silicic acid 5% 5%] Kaolin % 40% Talc %
[00368] The active ingredient is carefully mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, resulting in powders that can be used directly for seed treatment. Emulsifiable concentrate active ingredient [formula compound 10% (I)] Petition 870250055585, dated 01 / 07 / 2025, p. 155 / 501 142 / 236 octylphenol ether and polyethylene glycol 3% (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3% castor oil polyglycol ether (354 mol ethylene oxide) % Cyclohexanone 30% xylene mixture 50%
[00369] Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water. Dust a) b) c) Active ingredient [compound of formula (I)] 5% 6% 4% talc 95% - Kaolin - 94% mineral filler - -96%
[00370] Ready-to-use powders are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. These powders can also be used for dry dressings for seeds. Extruder granules Petition 870250055585, dated 01 / 07 / 2025, page 156 / 501 143 / 236 Active ingredient [compound of formula (I) 15%] sodium lignosulfonate 2% carboxymethylcellulose 1% Kaolin 82%
[00371] The active ingredient is mixed and ground with the excipients and the mixture is moistened with water. The mixture is extruded and then dried in an air stream. Coated granules Active ingredient [compound of formula (I)] 8% polyethylene glycol (p. mol. 200) Kaolin 89
[00372] The finely ground active ingredient is uniformly applied, in a mixer, to kaolin moistened with polyethylene glycol. Powder-free coated granules are obtained in this way. Concentrated suspension active ingredient [compound of formula (I)] 40% propylene glycol 10% Petition 870250055585, dated 01 / 07 / 2025, page 157 / 501 144 / 236 nonylphenol ether polyethylene glycol (15 mol 6% ethylene oxide) Sodium lignosulfonate 10% carboxymethylcellulose 1% silicone oil (in the form of a 1% emulsion in water) Water 32%
[00373] The finely ground active ingredient is intimately mixed with the adjuvants, giving a concentrated suspension from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion. Concentrate suitable for flow for seed treatment active ingredient [compound of formula (I)] 40% propylene glycol 5% Butanol PO / EO 2% copolymer with 10-20 moles of EO 2% 1,2-benzisothiazolin-3-one (in the form of a 0.5% solution at 20% in water) calcium salt of monoazo pigment 5% Silicone oil (in the form of a 0.2% emulsion) 75% water Water 45.3% Petition 870250055585, dated 01 / 07 / 2025, page 158 / 501 145 / 236
[00374] The finely ground active ingredient is intimately mixed with the adjuvants, giving a concentrated suspension from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, live plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion. Slow-Release Capsule Suspension
[00375] 28 parts of a combination of the compound of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of a mixture of toluene diisocyanate / polymethylene polyphenyleneisocyanate (8:1). This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent and 51.6 parts water until the desired particle size is achieved. To this emulsion is added a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water. The mixture is stirred until the polymerization reaction is complete.
[00376] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The average capsule diameter is 8-15 microns.
[00377] The resulting formulation is applied to the seeds as an aqueous suspension in an apparatus suitable for that purpose. Examples Petition 870250055585, dated 01 / 07 / 2025, page 159 / 501 146 / 236
[00378] The following Examples serve to illustrate the invention. The compounds of the invention can be distinguished from known compounds by virtue of greater effectiveness at low application rates, which can be verified by a person skilled in the art using the experimental procedures outlined in the Examples, using lower application rates if necessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm or 0.2 ppm.
[00379] Compounds of formula (I) may possess any number of benefits including, inter alia, advantageous levels of biological activity to protect plants against diseases caused by fungi or superior properties for use as agrochemical active ingredients (e.g., higher biological activity, an advantageous spectrum of activity, an enhanced safety profile (including improved crop tolerance), improved physicochemical properties or increased biodegradability). List of Abbreviations
[00380] °C = degrees Celsius, CDCI3 = chloroformd, d = doublet, DIPEA = N,N-diisopropylethylamine, DMF = dimethylformamide, HAUT = 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazol[4,5b]pyridinium 3-oxide hexafluorophosphate, m = multiplet, MHz = megahertz, N = normal, s = singlet In general
[00381] Throughout this description, temperatures are given in degrees Celsius (°C) and mf means melting point. LC / MS means Chromatography Petition 870250055585, dated 01 / 07 / 2025, page 160 / 501 147 / 236 Liquid-based mass spectrometry, and the description of the apparatus and method is as follows:
[00382] Method A: Waters ACQUITY UPLC, Waters HSS T3 UPLC, 1.8 µm particle size, 30 x 2.1 mm column, 0.85 mL / min, 60 °C, H2O / MeOH 95:5 + HCOOH 0.05% (90%) / CH3CN + 0.05% HCOOH (10%) - 1.2 min. - CH3CN + 0.05% HCOOH (100%) - 0.30 min., Mass Spectrometer Waters' ACQUITY SQD, ionization method: Electrospraying (ESI), Polarity: positive ions, Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 350, Cone Gas Flow (L / Hr) 0, Gas Flow of Desolvation (L / Hr) 650).
[00383] Method B: Waters ACQUITY UPLC, UPLC Waters HSS T3, particle size 1.8 µm, 30 x 2.1 mm column, 0.85 mL / min, 60 °C, H2O / MeOH 95:5 + HCOOH 0.05% (90%) / CH3CN + 0.05% HCOOH (10%) - 2.7 min. - CH3CN + 0.05% HCOOH (100%) - 0.30 min., Mass Spectrometer Waters' ACQUITY SQD, ionization method: Electrospraying (ESI), Polarity: positive ions, Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, Source Temperature (°C) 150, Desolvation Temperature (°C) 350, Cone Gas Flow (L / Hr) 0, Gas Flow of Desolvation (L / Hr) 650).
[00384] Method C: Spectra were recorded on a Waters Corporation ACQUITY Mass Spectrometer (Single Quadrupole Mass Spectrometer SQD or SQDII) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.0 kV, Cone: 30 V, Extractor: 3.00 V, Source Temperature: 150 °C, Temperature Petition 870250055585, dated 01 / 07 / 2025, p. 161 / 501 148 / 236 Desolvation: 400 °C, Cone Gas Flow: 60 L / hr, Desolvation Gas Flow: 700 L / h, Mass Range: 140 to 800 Da and a Waters Corporations ACQUITY UPLC with solvent degasser, binary pump, heated column compartment and diode array detector. Column: Waters HSS T3 UPLC, 1.8 µm, 30 x 2.1 mm, Temp: 60 °C; DAD wavelength range (nm): 210 to 400, Solvent Gradient: A = Water / Methanol 9:1 + 0.1% formic acid, B = Acetonitrile + 0.1% formic acid, gradient: B 0-100% in 2.5 min; Flow rate (mL / min) 0.75). Example 1: a) Preparation of 6-(3,5-difluoroaniline)-N-(2,2-dimethylcyclobutyl)-4-methoxypyridine-2-carboxamide (Table 3, Compound P-101) (Compound P-101) Step A: Preparation of 6-chloro-N-(2,2-dimethylcyclobutyl)-4-methoxypyridine-2-carboxamide
[00385] 2,2-dimethylpropan-lamine (1.1 equiv.), 1[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5] hexafluorophosphate were added Petition 870250055585, dated 01 / 07 / 2025, page 162 / 501 149 / 236 [b]pyridinium 3-oxide (HATU, 1.1 equiv.) and N,N-diisopropylethylamine (2.6 equiv.) were subsequently mixed with a DMF solution (15.7 mL) of 6-chloro-4-methoxypyridine-2-carboxylic acid (300 mg, 1.57 mmol, 1 equiv.). The resulting solution was stirred at room temperature for 1 h until the starting material was consumed (LCMS control). Then, a saturated solution of NaHCO3 was added to the mixture and the solution was extracted three times with ethyl acetate, the combined organic phases were dried over sodium sulfate and all volatiles were removed by rotary evaporator. Purification by silica gel column chromatography (eluent: cyclohexane / ethyl acetate mixtures) yielded the desired product 6-chloro-N-(2,2-dimethylcyclobutyl)-4-methoxypyridine-2-carboxamide. ^-NMR (400 MHz, CDC13): δ = 1.13 (s, 3H), 1.22 (s, 3H), 1.60-1.65 (m, 2H), 1.90-2.00 (m, 1H), 2.28-2.35 (m, 1H), 3.93 (s, 3H), 4.27-4.35 (q, 1H), 6.93-6.97 (d, 1H), 7.66-7.70 (d, 1H), 7.90-7.94 (m, 1H). Step B: a) Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-4-methoxypyridine-2-carboxamide (Table 3, Compound P-101) Compound P-101
[00386] G3-palladium Under an argon atmosphere, BrettPhos ( [ (2-Di-cyclohexylphosphino-3,6-dimethoxy Petition 870250055585, dated 01 / 07 / 2025, page 163 / 501 150 / 236 2',4',6'-tri-isopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate (0.1 equiv.) and potassium tert-butoxide (2.5 equiv.) were added to a stirred, degassed mixture of 6-chloro-N-(2,2-dimethylcyclobutyl)-4-methoxypyridine-2-carboxamide (100 mg, 0.37 mmol, 1 equiv.) and 3,5-difluoroaniline (1.1 equiv.) in THF (1.5 mL). The reaction was heated under reflux and stirred for 1 hour, then the mixture was cooled to room temperature and ethyl acetate was added to the mixture. The organic layer was washed with a saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate, and concentrated under vacuum. Purification by silica gel column chromatography (eluent: cyclohexane ethyl acetate mixtures) yielded the desired methyl 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-4-methoxypyridine-2-carboxamide. 1H-NMR (400 MHz, (CDshSO): δ = 1.08-1.13 (m, 6H), 1.45-1.60 (m, 2H), 1.86-2.00 (m, 1H), 2.10-2.20 (m, 1H), R (s, 1H). Example 2: a) Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-3-methoxypyridine-2-carboxamide (Table 3, Compound P-22) (Compound P-22) Petition 870250055585, dated 01 / 07 / 2025, p. 164 / 501 151 / 236 Step A: Preparation of methyl 6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxylate F
[00387] Under an argon atmosphere, BrettPhos-G3-palladacyclo methanesulfonate ([(2-Dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate, 0.1 equiv.) and cesium carbonate (2.5 equiv.) were added to a degassed stirred mixture of methyl 6-bromo-3-methoxypyridine-2-carboxylate (700 mg, 2.84 mmol, 1 equiv.) and 3,5-difluoroaniline (1.1 equiv.) in THF (11.4 mL). The reaction was heated to 80 °C and stirred for 1 h, then the mixture was cooled to room temperature. Volatiles were removed using a rotary evaporator and the residue was dissolved in ethyl acetate. The organic phase was washed twice with water, dried over anhydrous sodium sulfate and concentrated under vacuum. Purification by silica gel column chromatography (eluent: cyclohexane / ethyl acetate mixtures) yielded the desired methyl 6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxylate. 1H-NMR (400 MHz, (CDshSO): δ = 3.80 (s, 3H), 3.85 (s, 3H), 6.55-6.63 (m, 1H), 7.07-7.12 (d, 1H), 7.42-7.50 (m, 2H), 7.65-7.72 (d, 1H). Step B: Preparation of 6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxylic acid Petition 870250055585, dated 01 / 07 / 2025, page 165 / 501 152 / 236 O F
[00388] Lithium hydroxide monohydrate (4 equiv.) was added to a solution of methyl 6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxylate (930 mg, 3.16 mmol) in a mixture of tetrahydrofuran (14 mL) and water (5 mL). The reaction mixture was stirred for 4 h at room temperature, and then the solvents were removed under vacuum. The residue was diluted with ethyl acetate and water, and then 2 N hydrochloric acid was added slowly until a pH of 3-4 was reached. The phases were separated and the aqueous phase was extracted three times with ethyl acetate. Then, the combined organic phases were dried over sodium sulfate and all volatiles evaporated using a rotary evaporator. The 6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxylic acid obtained was used directly in the next step without further purification. Step C: a) Preparation of 6-(3,5-difluoroanilino)N-(2,2-dimethylpropyl)-3-methoxypyridine-2-carboxamide (Table 3, Compound P-22) THE (Compound P-22)
[00389] 2,2-dimethylpropan-lamine (1.1 equiv.), hexafluorophosphate of 1 Petition 870250055585, dated 01 / 07 / 2025, page 166 / 501 153 / 236 [Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5b]pyridinium 3-oxide (HATU, 1.1 equiv.) and N,N-diisopropylethylamine (2.6 equiv.) were sequentially mixed with a DMF solution (3.6 mL) of 6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxylic acid (100 mg, 0.36 mmol, 1 equiv.). The resulting solution was stirred at room temperature for 1 h until the starting material was consumed (LCMS control). Then, a saturated solution of NaHCO3 was added to the mixture and the solution was extracted three times with ethyl acetate, the combined organic phases were dried over sodium sulfate and all volatiles were removed by rotary evaporator. Purification by silica gel column chromatography (eluent: cyclohexane / ethyl acetate mixtures) yielded the desired product 6(3,5-difluoroanilino)-N-(2,2-dimethylpropyl)-3-methoxypyridine-2-carboxamide. ^-NMR (400 MHz, CDC13): δ = 1.00 (s, 9H), 3.28 (d, 2H), 3.97 (s, 3H), 6.40-6.50 (m, 1H), 6.75 - 6.90 (m, 3H), 7.05 - 7.10 (d, 1H), 7.40-7.45 (d, 1H), 7.80-7.85 (m, 1H). Example 3: a) Preparation of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-prop-2-inox- Petition 870250055585, dated 01 / 07 / 2025, p. 167 / 501 154 / 236 Step A: Preparation of 6-(3,5-difluoroanilino)-3-hydroxypyridine-2-carboxylic acid OH F
[00390] In a flask, under an argon atmosphere, 6-bromo-3-hydroxy-pyridine-2-carboxylic acid (CAS: 321596-58-1, 0.8 g, 3.66 mmol) was dissolved in tert-butanol (18 mL). To this solution, cesium carbonate (2.39 g, 7.33 mmol) was added followed by 3,5-difluoroaniline (CAS: 372-39-4, 0.71 g, 5.50 mmol). The resulting suspension was purged with argon, ROCKPHOS Pd G3 (0.31 g, 0.36 mmol) was added, and the resulting brown suspension was heated to 75 °C and stirred at this temperature overnight. The reaction mixture was cooled to room temperature and poured into water and ethyl acetate. The aqueous layer was washed with ethyl acetate. Then, the pH of the aqueous layer was adjusted to pH 7 and the phase was extracted twice with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated to provide 6-(3,5-difluoroanilino)-3-hydroxypyridine-2-carboxylic acid. 1H NMR (400 MHz, DMSO) δ ppm 6.44 - 6.56 (m, 1 H) 6.90 (d, J=8.80 Hz, 1 H) 7.14 (d, J=8.80 Hz, 1 H) 7.48 (dd, J=11.00, 2.20 Hz, 2 H) 9.18 (s, 1 H) 14.21 - 16.05 (m, 1 H) LC-MS (method A): 267 [M+H], Rt: 0.77 min Step B: Preparation of 6-(3,5-difluoroanilino)-N(2,2-dimethylcyclobutyl)-3-hydroxypyridine-2-carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 168 / 501 155 / 236
[00391] To a solution of 6-(3,5-difluoroanilino)-3-hydroxypyridine-2-carboxylic acid (0.557 g, 2.09 mmol) in N,N-dimethylformamide (21 mL) was added 2,2-dimethylcyclobutanamine hydrochloride (0.312 g, 2.30 mmol). Then, N,N-diisopropylethylamine (0.547 mL, 3.14 mmol) and HATU (1.19 g, 3.14 mmol) were added slowly. The reaction mixture was stirred at room temperature for 3 hours, and then HATU (0.398 g, 1.05 mmol) was added again and the resulting mixture was stirred at room temperature for a further 1 hour. The reaction mixture was quenched with aqueous saturated sodium bicarbonate and diluted with water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to provide 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-hydroxypyridine-2-carboxamide. 1H NMR (400 MHz, Chloroform) δ ppm 1.17 -1.23 (m, 6 H) 1.58 - 1.69 (m, 2 H) 1.94 (dd, J=11.19, 9.72 Hz, 1 H) 2.28 - 2.40 (m, 1 H) 4.29 (q, J=8.93 Hz, 1 H) 6.41 -6.52 (m, 2 H) 6.88 - 6.92 (m, 1 H) 6.93 - 7.00 (m, 2 H) 7.297.33 (m, 1 H) 7.80 - 7.91 (m, 1 H) 11.87 (s,1 H) LC-MS (method A): 348 [M+H], Rt: 1.27 min Petition 870250055585, dated 01 / 07 / 2025, p. 169 / 501 156 / 236 Step C: a) Preparation of 6-(3,5-difluoroanilino)N-(2,2-dimethylcyclobutyl)-3-prop-2-ynexopyridine-2-carboxamide (Table 3, Compound P-86) (Compound P-86)
[00392] To a solution of 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-hydroxypyridine-2-carboxamide (0.080 g, 0.23 mmol) in N,N-dimethylformamide (1.2 mL, 15 mmol) were added 3-bromoprop-1-yne (80% in xylene) (0.028 mL, 0.25 mmol) and potassium carbonate (0.035 g, 0.25 mmol). The resulting mixture was stirred at room temperature for 1 hour. LCMS analysis showed complete conversion. The reaction mixture was quenched with water and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to provide 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-prop-2-ynexypyridine-2-carboxamide. 1H NMR (400 MHz, Chloroform) δ ppm 1.14 (s,3 H) 1.21 (s, 3 H) 1.55 - 1.70 (m, 2 H) 1.88 (dd, J=11.37,9.54 Hz, 1 H) 2.27 - 2.39 (m, 1 H) 2.55 (t, J=2.38 Hz, 1 H) 4.34 (q, J=8.93 Hz, 1 H) 4.84 - 4.88 (m, 2 H) 6.48 (tt, J=8.99 2.20 Hz, 1 H) 6.61 (s, 1 H) 6.94 - 7.04 (m, 3 H) 7.57(d, J=8.80 Hz, 1 H) 7.72 (dl, J=8.44 Hz, 1 H) LC-MS (method A): 386 [M+H], Rt: 1.13 min Petition 870250055585, of 01 / 07 / 2025, p. 170 / 501 157 / 236 Example 4: Preparation of 6-[(2,6-difluoro-4pyridyl)amino]-N-(2,2-dimethylpropyl)-3-hydroxy-pyridine-2carboxamide (Table 3, Compound P-100) (Compound P100)
[00393] A mixture of 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylpropyl)-3-methoxypyridine-2-carboxamide (0.580 g, 1.66 mmol) and pyridine hydrochloride (0.976 g, 8.28 mmol) was heated to 150 °C to give a light brown solution. This solution was stirred for 16 hours at 150 °C. After cooling to room temperature, the reaction mixture was diluted with dichloromethane and loaded into Isolute. This crude product was purified by silica gel chromatography to give 6-[(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylpropyl)-3-hydroxypyridine-2-carboxamide. 1H NMR (400 MHz, DMSO d6) δ ppm 0.94 - 0.98 (s.9 H) 3.16 - 3.22 (d, 2 H) 7.09 - 7.13 (s, 2 H) 7.14 - 7.19(d, H) 7.42 - 7.54 (d, 1 H) 8.24 - 8.42 (m, 1 H) 10.11 -10.26 (s, 1 H) 12.04 - 12.19 (s, 1 H) LC-MS (method A): 337[M+H], Rt: 1.15 min Example 5: Preparation of 6-(N-cyano-3,5-difluoroanilino)N-(2,2-dimethylcyclobutyl)-3-methoxypyridine-2-carboxamide (Table 3, Compound P-20) Petition 870250055585, dated 01 / 07 / 2025, p. 171 / 501 158 / 236 (Compound P-20)
[00394] 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxypyridine-2-carboxamide prepared as described above for compound P-86 (0.0600 g, 0.166 mmol) was dissolved in tetrahydrofuran (0.830 mL) under an argon atmosphere and the resulting solution was cooled to -78 °C. Then, 1.6 M N-butyllithium in hexane (0.13 mL, 0.214 mmol) was carefully added dropwise using a syringe. The resulting mixture was stirred for 30 min at -78 °C and cyanogen bromide (0.0370 g, 0.332 mmol) was carefully added. The mixture was stirred for 30 min at -78 °C and then warmed to room temperature and stirred for 2 hours. The reaction mixture was deactivated with 20 mL of saturated NaHCO3 solution at 10 °C. The aqueous phase was extracted three times with ethyl acetate (15 mL). The organic phases were combined, washed with water (2 x 10 mL) and brine (1 x 10 mL), dried over sodium sulfate, and evaporated.The crude product was purified by silica gel chromatography to obtain 6-(N-cyano-3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxypyridine-2-carboxamide. 1H NMR (400 MHz, Chloroform) δ ppm 1.03 (s, 3 H) 1.18 (s, H) 1.52 - 1.68 (m, 2 H) 1.79 (dd, J=11.00, 9.54 Hz, 1 H) 2.22 - 2.33 (m, 1 H) 4.00 (s, 3 H) 4.27 (q, J=8.68 Hz, 1 H) 6.85 (s, 1 H) 7.01 (dd, J=7.70, 2.20 Hz, 2 H) 7.37 (d, J=8.80 Hz, 1 H) 7.55 (d, J=8.80 Hz, 2 H) Petition 870250055585, dated 01 / 07 / 2025, p. 172 / 501 159 / 236 LC-MS (method A): 387[M+H], Rt: 1.07 min Example 6: Preparation of [6-(3,5-difluoro-N-(2-methoxyacetyl)anilino)-2-[(2,2-dimethylcyclobutyl)carbamoyl]3-pyridyl]2-methoxyacetate (Table 3, Compound P-24) (Compound P-24)
[00395] 6-(3,5-difluoroanilino)-N-(2,2-dimethylcyclobutyl)-3-methoxypyridine-2-carboxamide (0.0370 g, 0.102 mmol) was suspended in methoxyacetyl chloride (0.410 mL, 4.48 mmol) under an argon atmosphere. The reaction mixture was heated and stirred for 20 hours at 90 °C and then for 6 hours at 100 °C. The reaction mixture was carefully quenched by the dropwise addition of NaHCO3 (20 mL). The aqueous phase was extracted with ethyl acetate (3 x 15 mL). The organic phases were combined, washed with water (2 x 10 mL) and brine (1 x 10 mL), dried, and evaporated under reduced pressure. The crude product was purified by silica gel chromatography to yield [6-(3,5-difluoro-N-(2-methoxyacetyl)anilino)-2-[(2,2-dimethylcyclobutyl)carbamoyl]3-pyridyl]2-methoxyacetate. 1H NMR (400 MHz, Chloroform) δ ppm 0.88 (s,3 H) 1.09 (s, 3 H) 1.48 - 1.68 (m, 3 H) 2.15 - 2.26 (m, 1 H) 3.43 (s, 3 H) 3.57 (s, 3 H) 4.03 (s, 2 H) 4.13 (m, 1 H) 4.44(d, J=0.73 Hz, 2 H) 6.93 (dd, J=6.79, 2.38 Hz, 2 H) 6.95 -7.03 Petition 870250055585, dated 01 / 07 / 2025, p. 173 / 501 160 / 236 (m, 1 H) 7.30 - 7.36 (m, 1 H) 7.59 (d, J=8.80 Hz, 1 H) 8.08 - 8.14 (m, 1 H) LC-MS (method A): 492 [M+H], Rt: 1.07 min Example 7: N-tert-butyl-6-(3,5-difluoroanilino)3-:methoxy-1-oxide-pyridin-1-ium-2-carboxamide (Table 3, Compound P-117) (Compound P-117)
[00396] A solution of N-tert-butyl-6-(3,5-difluoroanilino)-3-methoxypyridine-2-carboxamide (0.100 g, 0.298 mmol, compound P-93, Table 3) in dichloromethane (3 mL) was cooled to 0 °C under argon and treated with urea peroxide and hydrogen (0.0309 g, 0.328 mmol) to give a pale brown cloudy solution. To this was added, dropwise, trifluoroacetic anhydride (0.127 g, 0.0838 mL, 0.596 mmol) and the resulting pale brown solution was allowed to warm to room temperature and stirred for 17 hours where LCMS showed the completion of the reaction. The reaction mixture was quenched with aqueous Na2SO3 and poured into a 0.5 M aqueous HCl solution. Extraction with dichloromethane, followed by washing the organic layer with aqueous NaHCO3 solution, and then drying over anhydrous Na2SO4 and vacuum concentration gave the crude product. This was purified by flash chromatography eluting with methanol / dichloromethane to give the compound in question as a yellow powder. 1H NMR (400 MHz, CDCl3) δ ppm 1.50 - 1.54 (s, 9 H) Petition 870250055585, dated 01 / 07 / 2025, p. 174 / 501 161 / 236 3.88 - 3.91 (s, 3 Η) 6.55 - 6.61 (m, 1 Η) 6.66 - 6.70 (m, 1 Η) 6.70 - 6.77 (m, 2 Η) 7.02 - 7.06 (d, 1 Η) 7.19 - 7.23 (d, 1 Η) 8.50 - 8.58 (s, 1 Η) . LCMS (Method A); 352 [M+H], Rt: 0.85 min Table 3 below illustrates individual compounds exemplified of formula (I) according to the invention. Table 3: Melting point and LC / MS data (Tr= Retention time) for selected compounds from Table 1 and Table 2. Pf Compound No. LC / MS structure Name (°C) 6-[(2,6difluoro-4pyridyl)amino]-N-(2,2P-1 dimethylcyclobutyl)-3hydroxypyridine-2carboxamide 6- (3,5difluoroaniline)-N- (2,2dimethylcyclo P-2butyl)-3hydroxypyridine-2- Rt = 1.17 min (A); 147 MS: m / z = 151.8 349.3 (M+l) Rt = 1.27 160.1 min (A); MS: m / z = 161.2 348.5 (M+l) carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 175 / 501 162 / 236 Compound No. Name 6-[(2,6difluoro-4Structure Pf LC / MS (°C) pyridyl)amine o] -3P-3 hydroxy-Nespiro[3.4]o ctan-3-yl- Rt = 1.24 165.8 min (A); MS : m / z = 168.6 375.4 (M+l) pyridine-2carboxamide 6-[(2,6difluoro-4pyridyl)amino]-N-(2,2P-4 dimethylcyclobutyl)-3methoxypyridine-2carboxamide N- (2,2- 154 156 Rt = 0.99 min (A); MS : m / z = 363.5 (M+1) dimethylcyclobutyl)-3methoxy-6P-5 (thiazol-2ylamino)pyri dina-2Rt = 1.04 min (A); MS : m / z = 333.4 (M+l) carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 176 / 501 163 / 236 No. Compound Name 6-[(2,6difluoro-4Structure Pf (°C) LC / MS P-6 pyridyl)amino]-3-methoxyNespiro[3.4]o ctan-3-yl- Rt = 1.06 min (A); MS : m / z = 389.5 (M+l) P-7 P-8 pyridine-2-carboxamide 6- (3,5difluoroanyl pyridine-2carboxamide 2-(3,54carboxamideino)-N-(2,2dimethylcyclobutyl)-3methoxy- difluoroaniline)-Nisopentyl-5methoxypyrimidine- Rt = 1.09 min (A); MS : m / z = 362.4 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 177 / 501 164 / 236 No. Compound Name Structure Pf (°C) LC / MS 2-[(2,6difluoro-4F. piridil)amine o] -NP-9 isopentyl-5methoxypyrimidine- 73 4-carboxamide 2-(3,5difluoroaniline)-N-(2,2dimethylcyclo P-10 butyl) -5methoxypyrimidine- 4-carboxamide 2-[(2,6-difluoro-4-pyridyl)amine o]-N-(2,2dimethylcyclo P-11 butyl)-5methoxy- NMR data: See footnote pyrimidine-4-carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 178 / 501 165 / 236 Compound No. Name N- (2,2-dimethylcyclo Structure Pf LC / MS (°C)butyl)-6[(5-fluoro3P-12 pyridyl)amine o] -3hydroxypyridine-2carboxamide N- (2,2-dimethylcyclo Rt = 1.71 min (C); MS: m / z = 331.15 (M+1)butyl)-6[ (6-fluoro3P-13 pyridyl)amin o] -3hydroxypyridine-2carboxamide Rt = 1.73 min (C); MS: m / z = 331.15 (M+l) 6- [ (2-chloro-4-pyridyl)amine P-14 o]-N-(2,2dimethylcyclobutyl)-3- Rt = 1.74 min (C); MS: m / z = 347.13 (M+l) hydroxy Petition 870250055585, dated 01 / 07 / 2025, p. 179 / 501 166 / 236 Compound No. Name: pyridine-2-carboxamide Structure Pf LC / MS (°C) N-(2,2dimethylcyclobutyl)-3hydroxy-6P-15(pyrimidin5ylamino)pyri Rt = 1.44 min (C); MS : m / z = 314.15 (M+l) dyna-2carboxamide 6-anilino-N(2,2-dimethylcyclo P-16 butyl) -3hydroxypyridine-2carboxamide 6- (1,3benzodioxol5-ylamino)N- (2,2P-17 dimethylcyclobutyl)-3hydroxypyridine-2carboxamide Rt = 1.95 min (C); MS : m / z = 312.18 (M+l) Rt = 1.86 min (C) ; MS : m / z = 356.17 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 180 / 501 167 / 236 Compound No. Name N- (2,2-dimethylcyclo Structure Pf LC / MS (°C)butyl)-6[(2-fluoro4P-18 pyridyl)amine o] -3- hydroxyRt = 1.68 (C); MS : m / z = 331.17 (M+l) pyridine-2carboxamide N-(2,2dimethylcyclobutyl)-3hydroxy-6P-19(isothiazol4ylamino)pyri Rt = 1.70 min (C); MS : m / z = 319.12 (M+l) dyna-2carboxamide 6-(N-cyano3,5difluoroanilino)-NP-20 (2,2dimethylcyclo Rt = 1.07 min (A); MS : m / z = 387 (M+l) butyl)-3methoxy Petition 870250055585, dated 01 / 07 / 2025, page 181 / 501 168 / 236 Compound No. Name: pyridine-2-carboxamide 6-[cyano(2,6difluoro-4pyridyl)amino]-N-(2,2P-21 dimethylcyclobutyl)-3methoxypyridine-2carboxamide 6-(3,5difluoroaniline)-N-(2,2P-22 dimethylpropyl)-3-methoxypyridine-2carboxamide Structure Pf LC / MS (°C) Rt = 1.02 min (A); MS: m / z = 388 (M+l) ch3 / --CH3 N CHSo ch3 Rt = 1.05 - min (A); MS : m / z = 350 (M+l) 6- (3,5difluoroaniline)-3P-23 methoxy-N- (2phenylpropyl) pyridine-2- Rt = 1.09 - min (A); 9 MS : m / z = 398 (M+l) carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 182 / 501 169 / 236 Compound No. Name Structure Pf (°C) LC / MS [6- (3,5difluoro-N(2methoxyacetyl)anilino)-2[(2,2P-24 dimethylcyclobutyl)carbarn oil]-3- 100 102 Rt = 1.07 min (A); MS: m / z = 492 (M+l) pyridyl] 2methoxyacetat N-benzyl-6(3,5-difluoroanyl P-25 ino)-3methoxypyridine-2- Rt = 1.02 min (A); MS: m / z = 370 (M+l) carboxamide 6- (3,5difluoroaniline)-N[ (3,5P-26 difluorophenyl 1)methyl]-3-methoxy- 90 Rt = 1.04 min (A); MS: m / z = 406 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 183 / 501 170 / 236 Compound No. Name 6- (3,5-difluoroanil Structure Pf (°C) LC / MS ino)-N-[2(4P-27fluorophenoxy)ethyl]-3methoxypyridine-2carboxamide 6- (3.5- ch3 Rt = 1.05 min (A); MS: m / z = 418 (M+1)difluoroaniline)-N-(4,4dimethylpentP-28 2-ynyl)-3methoxypyridine-2carboxamide 6-[(2,6- 63 Rt = 1.10 min (A); MS: m / z = 374 (M+1)difluoro-4pyridyl)amine o] -NP-29 isopentyl-3methoxypyridine-2carboxamide Rt = 0.97 min (A); MS : m / z = 351 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 184 / 501 171 / 236 Compound No. Name Structure Pf LC / MS (°C) 6-[(2,6-difluoro-4-pyridyl)amine o]-N-(2,2P-30 dimethylpropi 1)-3-methoxypyridine-2carboxamide 6-[(2,6- 60 Rt = 0.96 min (A); MS : m / z = 351 (M+l)difluoro-4pyridyl)amine o]-3-methoxyP-31 N- (2phenylethyl) pyridine-2carboxamide 6-[(2,6- Rt = 0.96 - min (A); MS : m / z = 385 (M+1) difluoro-4pyridyl)amine o]-3-methoxyP-32 N-(2-phenylpropyl)pyridine-2- Rt = 1.00 min (A); MS : m / z = 398 (M+l) carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 185 / 501 172 / 236 Compound No. Name 6Structure Pf LC / MS (°C) (isothiazol4-ylamino)3-methoxy-NP-33 spiro[3.4]or ctan-3-yl- 125 128 Rt = 0.97 min (A); MS : m / z = 359 (M+l) pyridine-2carboxamide N- (4,4dimethylpent2-inyl)-6(isothiazolP-34 4-ylamino)3-methoxy- Rt = 1.01 min (A); MS: m / z = 345 (M+l) pyridine-2carboxamide 6-[(2,6difluoro-4pyridyl)amine o]-N-(4,4P-35 dimethylpent2-inyl)-3methoxy- Rt = 1.01 178 - min (A); 182 MS: m / z = 375 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 186 / 501 173 / 236 Compound Pf Not. Structure Name (°C) LC / MS N- (1,5dimethylhexyl )-6(isothiazolP-36 4-ylamino)3-methoxyS—N CH3 86 Rt = 1.07 min (A); MS: m / z = 363 (M+l) pyridine-2carboxamide N- [ (4chlorophenyl)m ethyl]-6(isothiazolP-37 4-ylamino)3-methoxypyridine-2- Rt = 0.93 min (A); MS: m / z = 375 (M+l) carboxamide N- [2- (3,5difluorophene xi)-1-methylethyl]-6P-38 (isothiazol4-ylamino)3-methoxy- Rt = 0.99 min (A); MS: m / z = 421 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 187 / 501 174 / 236 Compound No. Name Structure Pf (°C) LC / MS N- [2-(2,4dichlorophenox i)ethyl]-6(isothiazolP-39 4-ylamino)3-methodipyridine-2carboxamide 6(cyclopropyl methylamino)N- (2,2P-40 dimethylprop 1)-3-methopyridine-2carboxamide Rt = 1.01 min (A); MS : m / z = 439 (M+l) Rt = 0.81 min (A); MS: m / z = 292 (M+l) (cyclobutyl amino)-N(2,2P-41 dimethylpropyl 1)-3-methoxypyridine-2carboxamide 6-(2,3-dihydroxypropyl P-42amino)-N(2,2- Rt = 0.82 min (A); MS : m / z = 292 (M+l) Rt = 0.63 min (A); MS: m / z = 312 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 188 / 501 175 / 236 Compound No. Name: dimethylprop 1)-3-methoxypyridine-2carboxamide N- (2,2-dimethylpropyl 1)-6-(2,2-H ΓΊ dimethylpropy P-43 lamino)-3methoxypyridine-2carboxamide 6-(3,5difluoroaniline)-N-(2,2dimethylcycloFP-44 butyl)-3ethoxypyridine-2carboxamide 6-(3,5difluoroaniline)-N-[2F P-45 (4fluorophenoxy )cyclobutyl] -3-methoxy- Rt = 1.15 152 - min (A); 157 MS: m / z = 376 (M+l) Pf LC / MS (°C) Rt = 0.89 min (A); MS: m / z = 308 (M+l) Rt = 1.61 min (C) ; MS: m / z = 444 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 189 / 501 176 / 236 Compound No. Name pyridine-2carboxamide 6- (3,5difluoroaniline)-3(difluorometh P-46 oxy)-N-(2,2dimethylcyclobutyl)pyridine-2carboxamide 6-[(2,6difluoro-4pyridyl)amino]-3-methoxyN-[5P-47(trifluoromethyl)indan-1yl]pyridine2carboxamide N-[(3benzylimidazol-4P-48 yl)methyl]-6[(2,6difluoro-4pyridyl)amine Structure Pf LC / MS (°C) Rt = 1.19 158 - min (A); 161 MS: m / z = 398 (M+l) Rt = min 1.85 (C); MS: m / z = 465 (M+l) Rt = 0.97 min (C); MS: m / z = 451 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 190 / 501 177 / 236 No. Compound Name o]-3-methoxypyridine-2carboxamide Structure Pf LC / MS (°C) P-49 P-50 P-51 6-[(2,6difluoro-4pyridyl)amino]-3-methoxyN-[[1(trifluoromethyl)cyclopropyl]methyl]pyridine-2carboxamide N-(5cyclopropylethration]-3-methoxypyridine-2carboxamide 6-[(2,6difluoro-4pyridyl)amino]-3-methoxy- hydrofuran3-yl)-6[(2,6difluoro-4pyridyl)amine ch3 Rt = 1.56 min (C); MS: m / z = 403 (M+l) Rt = 1.37 min (C); MS: m / z = 391 (M+l) Rt = 1.27 min (C); MS: m / z = 426 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pages 191 / 501 178 / 236 Compound No. Name N-[(1methylpyrazole [3,4b]pyridin-3yl)methyl]pyridine-2carboxamide Structure Pf LC / MS (°C) 6-[(2,6difluoro-4pyridyl)amino]-3-methoxyN-[(8-methylP-52 5oxaspiro[3.5 ]nonan-8yl)methyl]pyr idine-2carboxamide 6-[(2,6difluoro-4- Rt = 1.59 min (C); MS: m / z = 433 (M+l) pyridyl)amine o]-3-methoxyN- [ (3P-53 methyltetrahy drofuran-3yl)methyl]pyr idine-2carboxamide Rt = 1.27 min (C); MS: m / z = 379 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 192 / 5 179 / 2 Compost No. Nome 6-[(2,6difluoro-4Structure Pf LC / MS (°C) pyridyl)amine o]-N-(7,7dimethyl-2P-54oxabicyclo[3.2.0]heptane6-yl)-3- Rt = 1.45 min (C); MS: m / z = 405 (M+l) methoxypyridine-2carboxamide 6-(3,5-difluoroanilino)-3methoxy-N-[5P-55(trifluoromer thyl)indan-1yl]pyridine2carboxamide Rt = 2.02 min (C); MS: m / z = 464 (M+l) 6-(3,5-difluoroaniline)-3P-56 methoxy-N-[6(trifluoromethyl)indan-1- Rt = 1.98 min (C); MS: m / z = 464 (M+l) yl]pyridinePetition 870250055585, of 07 / 01 / 2025, p. 193 / 501 180 / 236 Compound No. Name 2-carboxamide Structure Pf LC / MS (°C) 6- (3,5difluoroaniline)-3P-57 methyl]pyridine-2Rt = 1.98 min (C); MS: m / z = 462 (M+l) carboxamide 6- (3,5difluoroaniline)-N[(2,2difluoroP-58 1,3benzodioxol4-yl)methyl]- Rt = 1.88 min (C); MS: m / z = 450 (M+l) 3-methoxypyridine-2-carboxamide 6- (3,5difluoroaniline)-3P-59 methoxy-N-(2oxabicyclo[3.2.0]heptan- Rt = 1.55 min (C); MS: m / z = 375 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 194 / 501 181 / 236 Compound No. Name 11) pyridine-2-carboxamide 6-(3,5-difluoroaniline)-N-(2,3dihydrobenzo P-60 furan-3ylmethyl)-3methoxypyridine-2carboxamide 6-(3,5-difluoroaniline)-3methoxy-N-(1tetraP-61hydropyran4ylethyl)pyridine-2carboxamide 6-(3,5-difluoroanil P-62 ino)-3- F methoxy-NStructure Pf LC / MS (°C) Rt = 1.72 min (C); MS: m / z = 412 (M+l) Rt = 1.54 min (C); MS: m / z = 392 (M+l) Rt = 1.7 6 min (C); MS: m / z = 402 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 195 / 501 182 / 236 No. Compound Name (trifluoromethyl)cyclopropyl]methyl]pyridine-2carboxamide Structure Pf LC / MS (°C) P-63 P-64 6- (3,5 — difluoroanyl methoxypyridine-2carboxamide 6-(3,5difluoroaniline)-3methoxy-N-(2oxaspiro[3.3]heptan-6yl)pyridine2carboxamidayne)-N-[[4(difluoromethyl)-1-methylpyrazol-3yl]methyl]-3- ch3 Rt = 1.48 min (C); MS: m / z = 424 (M+l) Rt = 1.38 min (C); MS : m / z = 376 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 196 / 501 183 / 236 Compound No. Name N-(5cyclopropyltetraFhydrofuran3-yl)-6P-65(3,5—difluoroaniline)-3methoxypyridine-2carboxamide N- [ (3,5dichloro-4pyridyl) met! 1]-6- (3,5P-66 difluoroanylFino)-3methoxypyridine-2carboxamide 6-(3,5difluoroanylfine)-3methoxy-N- P-67 [(8-methyl-5oxaspiro[3.5 ]nonan-8yl)methyl]pyr Structure Pf LC / MS (°C) Rt = 1.5 9 min (C); MS: m / z = 390 (M+l) Rt = 1.68 min (C); MS: m / z = 439 (M+l) Rt = 1.80 min (C); MS: m / z = 432 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 197 / 501 184 / 236 Compound No. Name: idine-2-carboxamide Structure Pf LC / MS (°C) 6- (3,5difluoroaniline)-3methoxy-N[ (3P-68 methyltetrahydrofuran3- Rt = 1.49 min (C); MS: m / z = 378 (M+1)yl)methyl]pyridine-2carboxamide 6- (3,5-difluoroanil yl)methyl]pyr Rt = 1.34 min (C); MS: m / z = 375 (M+l) idine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, pp. 198 / 501 185 / 236 Compound No. Name Structure Pf LC / MS (°C) 6- (3,5difluoroanilyne)-3methoxy-N-(4P-70 oxaspiro[2.4 ]heptan-6yl)pyridine2carboxamide 6- (3,5-difluoroanil Rt = 1.54 min (C); MS: m / z = 376 (M+1)yne)-3methoxy-N-[1(5P-71 methyloxazol2yl)ethyl]pyridine-2- Rt = 1.55 min (C); MS : m / z = 389 (M+l) carboxamide 6- (3,5difluoroaniline)-3methoxy-NP-72 [[1- [5(trifluoromethyl)-2- Rt = 1.93 min (C); MS : m / z = 479 (M+l) pyridyl]cyclopropyl]methi Petition 870250055585, dated 01 / 07 / 2025, pp. 199 / 501 186 / 236 Compound No. Name 1]pyridine2-carboxamide N-[[1-(6chloro-3pyridyl)cyclopropyl]met! 1]-6- (3,5P-73 difluoroaniline)-3methoxypyridine-2carboxamide 6-(3,5-difluoroaniline)-3methoxy-N-[2[4P-74(trifluoromethoxy)phenyl]ethyl]pyridine-2carboxamide N-[2-(3,5dichloro-2P-75 pyridyl)-2ethoxyiminoethyl1-6Structure Pf LC / MS (°C) Rt = 1.73 min (C); MS: m / z = 445 (M+l) Rt = 1.98 min (C); MS: m / z = 468 M+l) Rt = 1.99 min (C); MS: m / z = 510 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 200 / 501 187 / 236 Compound No. Name (3,5-difluoroaniline)-3-methoxypyridine-2-carboxamide Structure Pf LC / MS (°C) 6-(3,5difluoroaniline)-N-(7,7dimethyl-2oxabicyclo[3 P-76 .2.0]heptan6-yl)-3methoxypyridine-2carboxamide 6-(3.5difluoroaniline)-N-(1isopropylsulful P-77 phonyl-4piperidyl) 3-methoxy- pyridine-2-carboxamide Rt = 1.66 min (C); MS: m / z = 404 (M+l) Rt = 1.5 6 min (C) ; MS : m / z = 469 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 201 / 501 188 / 236 Compound No. Name 6-(3,5difluoroaniline)-N-(1,1dioxothian-4P-78 11)-3methoxypyridine-2carboxamide 6(isothiazole4-ylamino)3-methoxy-N[5P-79(trifluorome thyl)indan-1yl]pyridine2Structure carboxamide (isothiazol4-ylamino)3-methoxy-NP-80 [ [2(trifluorome thyl)pyrimide S —N n-5il]methyl]pyr Pf (°C) LC / MS Rt = 1.26 min (C); MS: m / z = 412 (M+l) Rt = 1.72 min (C); MS: m / z = 435 (M+l) Rt = 1.26 min (C); MS: m / z = 411 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 202 / 5 189 / 2 When. Compound Nome idine-2carboxamide Structure Pf LC / MS (°C) 6P-81 P-82 (isothiazol4-ylamino)3-methoxy-N[ (4phenoxyphenyl) methyl]pyridine-2carboxamide N- [(2,2difluoro1,3benzodioxol4-yl)methyl]6(isothiazol4-ylamino)3-methoxy- P-83 pyridine-2carboxamide 6(isothiazol4-ylamino)3-methoxy-N[ [i(trifluorom Rt = min 1.70 (C); MS: m / z = 433 (M+l) Rt = 1.57 min (C); MS: m / z = 421 (M+l) Rt = 1.41 min (C); MS: m / z = 373 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 203 / 501 190 / 236 Compound No. Useful name)cyclopro pil]methyl]pyridine-2carboxamide 6(isothiazol4-ylamino)3-methoxy-N[(8-methyl-5P-84 oxaspiro[3.5 ]nonan-8yl)methyl]pyridine-2carboxamide 6(isothiazol4-ylamino)3-methoxy-N[2-[4P-85(trifluoromethoxy)phenyl]ethyl]pyridine-2carboxamide Structure Pf LC / MS (°C) Rt = 1.44 min (C); MS: m / z = 403 (M+l) Rt = 1.68 min (C); MS : m / z = 439 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 204 / 501 191 / 236 No. Compound Name Structure Pf LC / MS (°C) 6- (3,5difluoroanil ino)-N-(2,2— dimethylcyclo P-8 6 butyl) -3prop-2inoxy- Rt = 1.13 min (A); MS : m / z = 386 (M+l) pyridine-2carboxamide 6- (3,5difluoroanil ino)-N-(2,2dimethylcyclo P-87 butyl)-3isopropoxypyridine-2- Rt = 1.19 min (A); MS : m / z = 390 (M+l) carboxamide N- (1cyclohexylci clopropyl) 6-[(2,6P-88 difluoro-4pyridyl)amine 185 187 o]-3-methoxyRt = 1.09 min (A); MS : m / z = 403 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 205 / 501 192 / 236 Compound Pf Not. LC / MS structure Name (°C) 6-[(2,6difluoro-4pyridyl)amine o]-N-[1-(4P-89 fluorophenyl)cyclopropyl] 221 223 Rt = 0.99 -3-methoxyme (A); MS: m / z = 415 (M+l) pyridine-2carboxamide N-[l-[ (4chlorophenyl)m ethyl]cyclopr opyl]-6[(2,6P-90 difluoro-4pyridyl)amine Rt = 1.06 min (A); MS: m / z = 445 (M+l) o]-3-methoxypyridine-2carboxamide N -tercbutyl-6[(2,6difluoro-4P-91 pyridyl)amine o]-3-methoxy- Rt = 0.96 153 - min (A); 155 MS: m / z = 337 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 206 / 501 193 / 236 No. Compound Name 6-[(2,6difluoro-4Structure Pf (°C) LC / MS P-92 pyridyl)amine or]-3-methoxyN- (1methylcyclopr opyl)pyridine Rt = 0.88 min (A); MS: m / z = 335 (M+l) P-94 and 2carboxamide N-tercP-93 butyl-6- Rt = 1.05 min (A); MS: m / z = 336 (M+l) pyridine-2carboxamide N-tercbutyl-6(3,5difluoroanil ino)-3ethoxy- Rt = 1.10 min (A); MS : m / z = 350 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 207 / 501 194 / 236 Compound No. Name Structure Pf (°C) LC / MS N-tertbutyl-6[(2,6difluoro-4P-95 pyridyl)amin o]-3-ethoxypyridine-2carboxamide N-terc- Rt = 1.01 min (A); MS: m / z = 351 (M+1) butyl-6(3,5difluoroanyl P-96 yne)-3-prop2-inoxypyridine-2carboxamide N-tertbutyl-6(3,5difluoroanyl P-97yne)-3isopropoxypyridine-2carboxamide N-tert-butyl-6P-98 [(2,6difluoro-4- Rt = 1.09 min (A); MS: m / z = 360 (M+l) Rt = 1.14 min (A); MS : m / z = 364 (M+l) Rt = 0.99 min (A); MS: m / z = 361 (M+l) Petition 870250055585, dated 01 / 07 / 2025, pp. 208 / 501 195 / 236 Compound No. Name: piridyl)amino]-3-prop-2-inoxypyridine-2-carboxamide Structure Pf LC / MS (°C) N-tertbutyl-6[(2,6difluoro-4P-99 pyridyl) amin o] -3isopropoxy- Rt = 1.06 min (A); MS: m / z = 365 (M+l) pyridine-2carboxamide 6-[(2,6-difluoro-4-pyridyl)amine o]-N-(2,2P-dimethylpropyl 100 1)-3hydroxy- Rt = 1.15 min (A); MS: m / z = 337 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, pages 209 / 501 196 / 236 Node. P101 P102 P103 P104 Compound Name 6-(3,5difluoroaniline)-N-(2,2—dimethylcyclobutyl)-4methoxypyridine-2carboxamide 6-[(2,6difluoro-4pyridyl)amino]-N-(1,5dimethylhexyl)-3-methoxypyridine-2carboxamide N-tertbutyl-6-[(5fluoro-3pyridyl)amine o]-3-methoxypyridine-2carboxamide N-(2,2dimethylcyclobutyl)-6[(5-fluoro3Structure Pf (°C) LC / MS Rt = 1.20 min (A); MS: m / z = 351 (M+l) Rt = 1.13 min (A); MS: m / z = 393 (M+l) Rt = 0.86 min (A); MS : m / z = 319 (M+l) Rt = 0.92 min (A); MS: m / z = 345 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 210 / 5 197 / 2 Compost No. Nome Structure Pf LC / MS (°C) pyridyl)amine o]-3-methoxypyridine-2carboxamide N-(2,2dimethylpropy 1)-6-[(5P-fluoro-3-n 105 pyridyl)amine o]-3-methoxypyridine-2carboxamide Rt = 0.88 182 - min (A); 187 MS: m / z = 333 (M+l) 6-[(2,6difluoro-3iodo-4pyridyl)amine P- o]-N-(2.2106 dimethylprop 1) -3- Rt = 1.2 5 min (A); MS: m / z = 463 (M+l) hydroxypyridine-2carboxamide 6-(3,5difluoroanyl P-ino)-3107 methoxy-N-(lmethylcyclope Rt = 1.11 min (A); MS: m / z = 362 (M+l) ntil)pyridine Petition 870250055585, dated 01 / 07 / 2025, p. 211 / 501 198 / 236 Compound No. Name the 2carboxamide Structure Pf LC / MS (°C) 6- (3,5difluoroanil ino)-3P-methoxy-N-(l108 methylcyclohe xyl)pyridine Rt = 1.15 min (A); MS: m / z = 376 (M+l) carboxamide 6-[(2,6difluoro-4pyridyl)amine o]-3-methoxyPN- (1109 methylcyclope ntyl)pyridine Rt = 1.01 min (A); MS: m / z = 363 (M+l) carboxamide 6-[(2,6difluoro-4pyridyl)amine o]-3-methoxyPN- (1110 methylcyclohexyl)pyridine 162 164 Rt = 1.06 min (A); MS: m / z = 377 (M+l) -2-carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 212 / 501 199 / 236 Compound No. Name Structure Pf (°C) 6- (3.5ch3difluoroanyl h3C ino)-N-(2.2 — Pdimethylpropy 111 1) pyridine-2-carboxamide CH3 LC / MS Rt = 1.13 min (A); MS : m / z = 320 (M+l) N-terc- -2- F Rt = 1.12 min (A); MS : m / z = 306 (M+l) carboxamide 6-[(2,6-difluoro-4-pyridyl)amine P- o]-N-(2,2113 dimethylpropi 1) pyridine- 174 177 Rt = 1.04 min (A); MS : m / z = 321 (M+l) 2-carboxamide N-tertbutyl-6P-[(2.6114 difluoro-4pyridyl)amin Rt = 1.03 min (A); MS : m / z = 307 (M+l) [pyridine] Petition 870250055585, dated 01 / 07 / 2025, p. 213 / 501 200 / 236 No. Compound Name 2-carboxamide Structure Pf LC / MS (°C) N- [ [3,5bis (trifluor P115 omethyl)phenyl]methyl]-6(3,5difluoroaniline)-3methoxy- Rt = 1.16 min (A); MS: m / z = 306 (M+l) pyridine-2carboxamide N-tercP116 P117 butyl-6(3,5difluoroaniline)-4methoxypyridine-2carboxamide N-tertbutyl-6(3,5difluoroaniline)-3methoxy-1- Rt = 1.15 min (A); MS: m / z = 336 (M+l) Rt = 0.85 min (A); MS: m / z = 352 (M+l) oxidopiridin-1 Petition 870250055585, dated 01 / 07 / 2025, page 214 / 501 201 / 236 No. Compound Name ium-2-carboxamide Structure Pf LC / MS (°C) 6- (3,5P118 difluoroanil ino)-3methoxy-N-(1methylcyclobu thyl)pyridine 82 Rt = 1.06 min (A); MS: m / z = 348 (M+l) -2carboxamide 6-(3.5P119 P120 Difluoroanil ino)-N-(1methylcyclop ntil)pyridine-2carboxamide 6-[(2,6difluoro-4pyridyl)amine o]-N-(1methylcyclop ntil)pyridine Rt = 1.18 min (A); MS: m / z = 332 (M+l) Rt = 1.09 min (A); MS : m / z = 333 (M+l)a-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 215 / 5 202 / 2 Compost No. Nome Structure Pf LC / MS (°C) N-(3cyanothiethane3-yl)-6(3,5Pdifluoroanil 121 ino)-3methoxypyridine-2carboxamide 6- (3,5difluoroanil ino)-3methoxy-N-(3Pmethyltetrahy 122 drofuran-3yl)pyridin- Rt = 0.93 133 - min (A); 134 MS: m / z = 364 (M+l) 2carboxamide N- (1cyanocyclope ntil)-6(3,5Pdifluoroanil 123 ino)-3methoxy- Rt = 1.00 - min (A); MS : m / z = 373 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 216 / 501 203 / 236 Compound No. Name 6-[(2,6difluoro-4Structure Pf LC / MS (°C) pyridyl)amine o]-3-methoxyP- N-(3124 methyltetrahi drofuran-3yl)pyridine- 160 161 Rt = 0.83 min (A); MS: m / z = 365 (M+l) 2carboxamide N- (1cyanocyclope ntil)-6[(2,6Pdifluoro-4125 pyridyl)amine o]-3-methoxy- Rt = 0.91 min (A); MS: m / z = 374 (M+l) pyridine-2carboxamide N- (1cyanocyclobe til)-6[(2,6Pdifluoro-4126 pyridyl)amine o]-3-methoxy- 197 198 Rt = 0.87 min (A); MS: m / z = 360 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 217 / 501 204 / 236 No. Compound Name 6-[(2,6difluoro-4Structure Pf LC / MS (°C) P127 pyridyl)amino]-3-methoxyN-(1methylcyclobutyl)pyridine Rt = 0.96 - min (A); 102 MS: m / z = 349 (M+l) -2-carboxamide 6- (3,5-difluoroanil P128 ino)-3methoxy-N-(3methyloxethan3yl)pyridine- Rt = 0.88 min (A); MS: m / z = 350 (M+l) 2-carboxamide N- (1P129 cyanocyclobutyl)-6- (3,5difluoroaniline)-3methoxy- Rt = 0.96 min (A); MS: m / z = 359 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 218 / 501 205 / 236 No. Compound Name Structure Pf (°C) 6- (3,5P130 dichloroanyl no)-N-(2,2dimethylpropyl 1)-3-methoxypyridine-2- LC / MS Rt = 1.86 min (C); MS : m / z = 382 (M+l) carboxamida 6- (3,4P131 dichloroanyl no)-N-(2,2dimethylpropyl 1)-3-methoxypyridine-2- Rt = 1.7 9 min (C); MS : m / z = 382 (M+l) carboxamida 6- (3-chloroP132 4-methylanilino)-N(2,2dimethylpropy 1)-3-methoxy- Rt = 1.7 8 min (C); MS : m / z = 362 (M+l) P133 pyridine-2carboxamide N-(2,2dimethylpropi 1)-6- (4fluoroaniline o)-3-methoxy- Rt = 1.51 min (C); MS : m / z = 332 (M+l) Petition 870250055585, 01 / 07 / 2025, pág. 219 / 501 206 / 236 No. Compound Structure Pf P134 P135 P136 Name (°C) LC / MS pyridine-2carboxamide 6- (3-chloro5-fluoro(2,21)-3-methoxypyridine-2carboxamide 6-(4-chloro3,5difluoroanilino)-N(2,21)-3-methoxypyridine-2carboxamide N-(2,2dimethylpropy 1)-6-[(2fluoro-4pyridine-2carboxamide aniline) -Nonmethylpropy F dimethylpropy pyridyl)amine o]-3-methoxy- Rt = 1.75 min MS : 366 m / z (M+l) Rt = 1.77 min MS : 384 m / z (M+l) Rt = 1.23 min MS : 333 m / z (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 220 / 5 207 / 2 Compost No. Nome Structure Pf LC / MS (°C) N-(2,2dimethylpropy 1)-6- (3Petylaniline) 137 -3-methoxypyridine-2carboxamide Rt = 1.69 min (C); MS: m / z = 342 (M+l) 6-(4-chloro3-methylanilino)-NP-(2,2138 dimethylpropylene 1)-3-methoxy- Rt = 1.77 min (C); MS: m / z = 362 (M+l) pyridine-2carboxamida N-(2,2dimethylpropi 1)-6- (3Pfluoroanilin 139 o)-3-methoxypyridine-2carboxamida N-(2,2dimethylpropi P1)-3-methoxy140 6- (3methylanilino Rt = 1.5 6 min (C); MS: m / z = 332 (M+l) Rt = 1.58 min (C); MS: m / z = 328 (M+l) Petition 870250055585, 01 / 07 / 2025, pág. 221 / 501 208 / 236 Compound No. Name Structure Pf LC / MS (°C) )pyridine-2carboxamida N-(2,2dimethylpropi 1)-3-methoxyP6- (4141 methylanilino)pyridine-2- Rt = 1.56 min (C); MS: m / z = 328 (M+l) carboxamida N-(2,2dimethylpropi 1)-6- (3fluoro-4Pmethyl142 anilino)-3methoxy- Rt = 1.66 min (C); MS: m / z = 346 (M+l) pyridine-2carboxamide 6- (3-cyano-5-methyl- Rt = 1.53 min (C) ; MS : m / z = 353 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 222 / 501 209 / 236 Compound No. Name Structure Pf LC / MS (°C) 6- (4-chloro3-fluoroanilino) -NP- (2.2144 dimethylpropyl 1)-3-methoxy- Rt = 1.71 min (C); MS: m / z = 366 (M+1) pyridine-2carboxamide N- (2,2-dimethylpropyl 1)-3-methoxyP- 6-(3,4,5145 trifluoroanilino)pyridine Rt = 1.69 min (C); MS: m / z = 368 (M+l) a-2carboxamide N-tertbutyl-6-(3P- cyanoanilino 146 )-3-methoxypyridine-2carboxamide Rt = 1.3 9 min (C); MS : m / z = 325 (M+l) N-tertbutyl-6-(3P-cyano-5147 fluoroanilino)-3methoxy- Rt = 1.51 min (C); MS: m / z = 343 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 223 / 501 210 / 236 Compound No. Name: pyridine-2-carboxamide Structure Pf (°C) LC / MS N-tertbutyl-6(3,5P-dichloroanil 148 no)-3-methoxypyridine-2-carboxamide N-tertbutyl-6(3,4P-dichloroanil 149 no)-3-methoxypyridine-2-carboxamide N-tertbutyl-3methoxy-6-[4P(trifluorome 150 til)anilino] pyridine-2carboxamide Rt = 1.85 min (C); MS: m / z = 368 (M+l) Rt = 1.77 min (C); MS: m / z = 368 (M+l) Rt = 1.69 min (C) ; MS : m / z = 368 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 224 / 501 211 / 236 Compound No. Name N-tertbutyl-6-(3chloro-4P- methyl151 anilino)-3methoxypyridine-2carboxamide N-tertbutyl-6-(3chloro-5P- fluoro152 anilino)-3methoxypyridine-2carboxamide N-tertbutyl-6-(4chloro-3,5P- difluoro153 anilino)-3methoxypyridine-2carboxamide Structure Pf (°C) LC / MS Rt = 1.74 min (C); MS: m / z = 348 (M+l) Rt = 1.73 min (C); MS: m / z = 352 (M+l) Rt = 1.7 6 min (C); MS : m / z = 370 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 225 / 5 212 / 2 Compost No. Nome Structure Pf LC / MS (°C) N-tertbutyl-6-[3fluoro-4P-(trifluorom 154 til)anilino] -3-methoxypyridine-2- Rt = 1.74 min (C); MS: m / z = 386 (M+l) carboxamide N-tertbutyl-6-(3P-chloroanilino 155 )-3-methoxypyridin-2- Rt = 1.64 min (C); MS: m / z = 334 (M+l) carboxamide N-tertbutyl-6-[(2fluoro-4Ppyridyl)amin 156 o]-3-methoxypyridine-2carboxamide 6(benzofuranP- 5-ylamino)157 N-tertbutyl-3methoxy- Rt = 1.17 min (C); MS: m / z = 319 (M+l) Rt = 1.38 min (C); MS: m / z = 340 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 226 / 501 213 / 236 No. Compound Name pyridine-2carboxamide Structure Pf LC / MS (°C) N-tercP158 P159 P160 butyl-6-(4chloro-3methylanilino)-3methoxypyridine-2carboxamide 6- (1,3benzodioxol5-ylamino)N-tertbutyl-3methoxypyridine-2carboxamide N-tertbutyl-6-(3fluoroanilino)-3-methoxypyridine-2- carboxamide Rt = 1.72 min (C); MS: m / z = 348 (M+l) Rt = 1.2 9 min (C); MS: m / z = 344 (M+l) Rt = 1.52 min (C) ; MS : m / z = 318 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 227 / 501 214 / 236 No. Compound Name Structure Pf (°C) P161 P162 P163 N-tertbutyl-3methoxy-6-(4methylanilino)pyridine-2carboxamide N-tertbutyl-3methoxy-6(3,4,5trifluoroanilino)pyridin-2carboxamide 2-carboxamide LC / MS Rt = 1.48 min (C); MS: m / z = 314 (M+l) Rt = 1.66 min (C); MS: m / z = 354 (M+l) Rt = 1.40 min (C); MS : m / z = 369 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 228 / 501 215 / 236 Compound No. Name Structure Pf LC / MS (°C) N-tertbutyl-6-(4cyano-3P- fluoro164 anilino)-3methoxypyridine-2carboxamide Rt = 1.44 min (C); MS: m / z = 343 (M+l) benzylindazo 1-6P- yl)amino]-N165 tert-butyl3-methoxypyridine-2carboxamide N-tert- Rt = 1.47 min (C); MS: m / z = 430 (M+l) butyl-3methoxy-6P- (pyrimidine166 5ylamino)pyridyne-2- . Rt = 0.95 min (C); MS : m / z = 302 (M+l) carboxamide 6-[(2,6p- difluoro-4167 pyridyl)amine o]-N-(1,2- Rt = 0.97 min (A); MS: m / z = 351 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 229 / 5 216 / 2 When. Compound Name dimethylpropy 1)-3-methoxypyridine-2carboxamide Structure Pf LC / MS (°C) 6-(3,5P168 difluoroanil ino)-N-(1,2dimethylpropy 1)-3-methoxypyridine-2carboxamide Rt = 1.06 min (A); MS: m / z = 350 (M+1) 6-[(2,6difluoro-4P169 pyridyl)amine o]-3-methoxyN-(1,2,2trimethylpropyl)pyridine- Rt = 1,01 min (A); MS: m / z = 365 (M+1) 2carboxamide 6-(3,5P170 difluoroanyl ino)-3methoxy-N(1,2,2trimethylprop Rt = 1.10 min (A); MS: m / z = 364 (M+l) pyridinePetição 870250055585, de 01 / 07 / 2025, pág. 230 / 501 217 / 236 Compound No. Name 2carboxamide Structure Pf (°C) LC / MS 6-(3,5difluoroanil ino)-3methoxy-NP(1,1,2,2171 tetramethylpropyl)pyridine a-2carboxamide Rt = 1.14 min (A); MS: m / z = 378 (M+1) 6-(3,5difluoroanilino)-3methoxy-NP(1,1,2172trimethylpropyl)pyridine2carboxamide 6-[(2,6difluoro-4pyridyl)amine Po]-3-methoxy173 N-(1,1,2-trimethylpropyl)pyridine- Rt = 1.11 min (A); MS: m / z = 364 (M+l) Rt = 1.01 min (A); MS: m / z = 365 (M+l) Petition 870250055585, dated 01 / 07 / 2025, p. 231 / 501 218 / 236 Compound No. Name 2-carboxamide Structure Pf LC / MS (°C) 6-[(2,6-difluoro-4-pyridyl)amine o]-3-methoxyPN- (1,1,2,2174 tetramethylpropyl)pyridin Rt = 1.05 min (A); MS : m / z = 379 (M+l) α-2-carboxamide 6-(3,5difluoroaniline)-N-(2,2P-dimethylcyclo 175 butyl)-3-methyl- Rt = 1.21 min (A); MS: m / z = 346 (M+l) pyridine-2carboxamide N-(1cyclobutylcyclobutyl)-6(3,5Pdifluoroanyl 176 yne)-3methoxy- Rt = 1.17 min (A); MS: m / z = 388 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 232 / 501 219 / 236 No. Compound Name N-[1-(6chloro-2Structure Pf (°C) LC / MS piridyl)cicl P177 obutyl]-6(3,5difluoroaniline)-3- 81 Rt = 1.10 min (A); MS: m / z = 445 (M+l) methoxypyridine-2carboxamide 6- (3.5P178 P179 difluoroanil Rt = 1.07 min (A); MS: m / z = 362 (M+l) Rt = 1.12 min (A); MS: m / z = 376 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 233 / 501 220 / 236 Compound No. Name Structure Pf LC / MS (°C) N- (1-tertbutylcyclobutyl)-6- (3.5 — P-difluoroanyl 180 ino)-3methoxy- 209 210 Rt = 1.16 min (A); MS: m / z = 390 (M+l) pyridine-2carboxamide 6-[(2,6-difluoro-4-pyridyl)amine o]-N-(1Pisopropylcic 181 lobutil)-3methoxypyridine-2carboxamide Rt = 1.03 - min (A); MS : m / z = 377 (M+l) N-(1cyclobutylcyclobutyl)-6[(2,6Pdifluoro-4182 pyridyl)amine o]-3-methoxy- Rt = 1.05 - min (?) ; 6 MS : m / z = 389 (M+l) pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 234 / 501 221 / 236 Compound No. Name 6-[(2,6difluoro-4Structure Pf LC / MS (°C) pyridyl)amine o]-N-(1Petilciclobut 183 il)-3methoxy- Rt = 0.98 - min (A); MS : m / z = 363 (M+l) pyridine-2carboxamide N- [1-(6-chloro-2-pyridyl)cyclo o]-3-methoxyRt = 1.02 min (A); MS: m / z = 446 (M+l) pyridine-2carboxamide N-(1-tertbutylcyclobutyl)-6[(2,6Pdifluoro-4185 pyridyl)amine o]-3-methoxyRt = 1.07 min (A); MS: m / z = 391 (M+l)pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 235 / 5 222. / 236 Compost No. Nome N-[1-(6chloro-3Structure Pf (°C) LC / MS pyridyl)cyclolbutyl]-6P- [(2,6186 difluoro-4pyridyl)amine 120 121 Rt = 0.95 min (A); MS: m / z = 446 (M+l) o]-3-methoxypyridine-2carboxamide N-[3-(4chlorophenyl)c iclobutyl]6-(3,5Pdifluoroanil 187 ino)-3methoxy- ch3 Rt = 1.15 min (A); MS: m / z = 444 (M+l)pyridine-2carboxamide N-[3-(4chlorophenyl)c iclobutyl]6-[(2,6Pdifluoro-4188 pyridyl)amine o]-3-methoxy- ch3 Rt = 1.07 min (A); MS: m / z = 445 (M+l)pyridine-2carboxamide Petition 870250055585, dated 01 / 07 / 2025, p. 236 / 501 223 / 236 Compound No. Name Structure Pf LC / MS (°C) 6-(N-acetyl-3,5-difluoroanilino)-NP-(2,2189-dimethylcyclobutyl)-3-methoxypyridine-2-carboxamide N-terc- 52 butyl-6-(2chloro-3,5P-difluoro190 aniline)-3methoxypyridine-2carboxamide methyl N(3,5difluorophenyl)-N-[6P[(2.2191 dimethylcyclobutyl) carbarn 100 Rt = 1.09 min (A); MS: m / z = 370 (M+l) oil]-5methoxy-2 Petition 870250055585, dated 01 / 07 / 2025, page 237 / 501 224 / 236 No. Compound Name pyridyl]carb amate Structure Pf LC / MS (°C) 6-[acetyl(2,6P192 difluoro-4pyridyl)amino]-N-(2,2dimethylcyclobutyl)-3methoxy- 59 P193 DMSO 4.08 1.96 (d, pyridine-2carboxamide N-[1-(6chloro-3pyridyl)cyclomethoxypyridine-2carboxamide obutyl]-6(3,5difluoroaniline)-3- Note: 1H NMR data for compound P-11 Rt = 1.04 min (A); MS : m / z = 445 (M+l) (400 MHz, d6) δ 10.74 (s, 1H), 8.63 - 8.56 (m, 2H), 7.35 (s, 2H), (d, J = 8.5 Hz, 1H), 3.87 (s, 3H), 2.08 - 2.05 (m, 1H), - 1.88 (m, 1H), 1.50 (dd, J = 16.3, 8.0 Hz, 2H), 1.07 = 29.6 Hz, 6H). Petition 870250055585, dated 01 / 07 / 2025, p. 238 / 501 225 / 236 Biological Examples: Example B1: Alternaria solani / tomato / leaf disc (alternaria leaf spot)
[00397] Tomato cv. Baby leaf discs are placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. The leaf discs are inoculated with a fungal spore suspension 2 days after application. The inoculated leaf discs are incubated at 23°C / 21°C (day / night) and 80% RH under a 12 / 12 h light / dark regime in a climate-controlled chamber, and the activity of a compound is evaluated as a percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated control leaf discs (5-7 days after application). The following compounds resulted in at least 80% control of Alternaria solani at 200 ppm when compared to untreated controls under the same conditions, which showed extensive disease development: P-4, P-6, P-7, P-10, P-22, P-44, P-45, P-55, P-56, P-60, P-62, P-65, P-66, P-67, P-68, P-70, P-74, P-76, P-78, P-83, P-86, P-87, P-91, P-93, P-94, P-107, P109, P-110, P-112, P-118, P-125, P-127, P-139, P-145, P-146, P-147, P-148, P-152, P-160, P-162, P-170, P-171, P-172, P173, P-176, P-178, P-179, P-180, P-185. Exempio__B2^_B°tryotinia_^fuçkeliana fBotrytis cinerea) / liquid culture (Gray mold)
[00398] Conidia of the cryogenically stored fungus are directly mixed into nutrient broth (Vogels broth). After placing a solution (DMSO) of the test compound in a microtiter plate (format of Petition 870250055585, dated 01 / 07 / 2025, page 239 / 501 226 / 236 wells), the nutrient broth containing the fungal spores is added. Test plates are incubated at 24 °C and growth inhibition is determined photometrically 3-4 days after application. The following compounds resulted in at least 80% control of Botryotinia fuckeliana at 20 ppm compared to untreated controls under the same conditions, which exhibit extensive disease development: P-7, P-42, P-93, P-112, P-116, P-118, P-119, P-120, P-132, P-134, P139, P-142, P-145, P-151, P-152, P-155, P-160, P-162, P-168, P-170, P-171, P-172, P-173, P-175, P-176, P-178, P-179, P189, P-190. Example B3: Glomerella lagenarium (Colletotrichum lagenarium) / liquid culture (Anthracnose)
[00399] Cryogenically stored fungal conidia are directly mixed into nutrient broth (potato broth and dextrose PDB). After placing a solution (DMSO) of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and growth inhibition is determined photometrically 3-4 days after application.The following compounds provided at least 80% control of Glomerella lagenarium at 20 ppm compared to the untreated control under the same conditions, which showed extensive disease development: P-1, P-2, P-3, P-4, P-6, P-7, P8, P-10, P-13, P-14, P-16, P-18, P-19, P-20, P-22, P-23, P-24, P-25, P-26, P-27, P-29, P-30, P-33, P-36, P-37, P-39, P-42, P-44, P-45, P-46, P-47, P-52, P-55, P-56, P-57, P-58, P-59, P-60, P-61, P-62, P-65, P-66, P-67, P-68, P-70, P-71, P-72, P-73, P-74, P-75, P-76, P-77, P-79, P-81, P-82, P-83, P-petition 870250055585, dated 01 / 07 / 2025, page 240 / 501. 227 / 236 84, P-85, P-86, P-87, P-88, P-90, P-91, P-93, P-94, P-95, P100, P-101, P-102, P-104, P-107, P-108, P-109, P-110, P-111, P-112, P-113, P-114, P-116, P-117, P-118, P-119, P-120, P121, P-122, P-123, P-127, P-128, P-129, P-130, P-131, P-132, P-133, P-134, P-136, P-137, P-138, P-139, P-140, P-141, P142, P-144, P-145, P-146, P-147, P-148, P-149, P-150, P-151, P-152, P-153, P-154, P-155, P-156, P-157, P-158, P-160, P161, P-162, P-163, P-165, P-168, P-170, P-171, P-172, P-173, P-175, P-176, P-177, P-178, P-179, P-180, P-187, P-189, P190, P-191. Example B4: Blumeria graminis f. sp. tritici (Erysiphe graminis f. sp. tritici) / wheat / preventive in leaf discs (powdery mildew in wheat)
[00400] Wheat cv. Kanzler leaf segments are placed on agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. Leaf discs are inoculated by shaking powdery mildew-infected plants over the test plates 1 day after application. The inoculated leaf discs are incubated at 20 °C and 60% RH under a 24 h light / dark regime followed by 12 h light / 12 h dark in a climate-controlled chamber, and the activity of a compound is evaluated as a percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated control leaf segments (6-8 days after application). The following compounds gave at least 80% control of Blumeria graminis f. sp.tritici at 200 ppm compared to an untreated control under the same conditions, which showed extensive disease development: PPetição 870250055585, dated 01 / 07 / 2025, p. 241 / 501. 228 / 236 4, P-6, P-7, P-9, P-10, P-11, P-20, P-21, P-22, P-25, P-26, P-29, P-30, P-44, P-45, P-48, P-50, P-51, P-52, P-53, P-54, P-57, P-59, P-61, P-62, P-64, P-65, P-67, P-68, P-70, P-74, P-76, P-83, P-91, P-92, P-93, P-94, P-95, P-103, P-104, P105, P-107, P-108, P-109, P-110, P-112, P-113, P-114, P-117, P-118, P-121, P-122, P-123, P-124, P-125, P-127, P-128, P134, P-139, P-145, P-147, P-152, P-153, P-156, P-160, P-162, P-164, P-166, P-167, P-168, P-169, P-170, P-171, P-172, P173, P-176, P-177, P-178, P-179, P-180, P-181, P-182, P-183, P-185, P-189, P-192. Example B5: Fusarium culmorum / liquid culture (fusariosis)
[00401] Conidia of the cryogenically stored fungus are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a solution (DMSO) of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and growth inhibition is determined photometrically 3-4 days after application. The following compounds yielded at least 80% control of Fusarium culmorum at 20 ppm compared with untreated controls under the same conditions, which exhibited extensive disease development: P-7, P-107, P-108, P-168, P-176, P-178, P-179. Example B6: Phaeosphaeria nodorum (Septoria nodorum) / wheat / leaf disc preventative (Glume blight)
[00402] Wheat leaf segments cv. Kanzler are placed on agar in a multi-well plate. Petition 870250055585, dated 01 / 07 / 2025, p. 242 / 501 229 / 236 (24-well format) and sprayed with the formulated test compound diluted in water. Leaf discs are inoculated with a fungal spore suspension 2 days after application. The inoculated test leaf discs are incubated at 20 °C and 75% RH under a 12 h light / 12 h dark regime in a climate-controlled chamber, and the activity of a compound is evaluated as a percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated control leaf segments (5-7 days after application). The following compounds provided at least 80% control of Phaeosphaeria nodorum at 200 ppm compared to an untreated control under the same conditions, which showed extensive disease development: P-4, P-7, P-22, P-25, P-26, P-27, P-44, P-45, P-46, P-55, P-56, P-57, P-62, P-93, P-94, P-107, P-112, P-116, P-118, P-139, P-145, P-146, P-152, P-160, P-171, P-172, P-176, P-178, P-179, P-180, P-189, P190. Example B7: Monographella nivalis (Microdochium nivale) / liquid culture (cereal foot rot)
[00403] Cryogenically stored fungal conidia are directly mixed into nutrient broth (potato broth and dextrose PDB). After placing a solution (DMSO) of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and growth inhibition is determined photometrically 4-5 days after application. The following compounds gave control of at least 80% of Monographella nivalis at 20 ppm compared to the control. Petition 870250055585, dated 01 / 07 / 2025, page 243 / 501 230 / 236 not treated under the same conditions, which showed extensive disease development: P-1, P-2, P-3, P-4, P-5, P-6, P7, P-8, P-10, P-12, P-13, P-14, P-15, P-16, P-17, P-18, P19, P-22, P-23, P-25, P-26, P-27, P-29, P-33, P-36, P-37, P38, P-39, P-40, P-43, P-44, P-45, P-46, P-47, P-55, P-56, P57, P-60, P-62, P-65, P-66, P-67, P-68, P-70, P-73, P-74, P75, P-76, P-79, P-81, P-82, P-83, P-86, P-87, P-91, P-93, P94, P-95, P-96, P-102, P-104, P-106, P-107, P-108, P-109, P110, P-111, P-112, P-113, P-114, P-117, P-118, P-119, P-120, P-121, P-122, P-123, P-127, P-131, P-132, P-133, P-134, P138, P-139, P-140, P-144, P-145, P-146, P-147, P-148, P-150, P-151, P-152, P-153, P-155, P-157, P-160, P-162, P-168, P170, P-171, P-172, P-173, P-175, P-176, P-177, P-178, P-179, P-180, P-181, P-183, P-185, P-187, P-189, P-190. Example B8: Mycosphaerella arachidis (Cercospora arachidicola) / liquid culture (early leaf necrosis)
[00404] Cryogenically stored fungal conidia are directly mixed into nutrient broth (potato broth and dextrose PDB). After placing a solution (DMSO) of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and growth inhibition is determined photometrically 4-5 days after application. The following compounds resulted in at least 80% control of Mycosphaerella arachidis at 20 ppm when compared to untreated controls under the same conditions, which showed extensive disease development: P-7, P-19, P-22, P-23, P-26, P-27, P-36, P-44, P-45, P-46, P-55, P-56, P-57, P-62, P-67, P-74, P-79, P-93, P-94, P-102, P-107, P-108, P-118, P-petition 870250055585, dated 01 / 07 / 2025, page 244 / 501 231 / 236 139, P-145, P-152, P-160, P-162, P-168, P-171, P-172, P-176, P-178, P-179, P-180. Example B9: Phakopsora pachyrhizi / soybean / preventative (soybean rust)
[00405] Soybean leaf discs are placed in water-agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. One day after application, the leaf discs are inoculated by spraying a spore suspension onto the lower leaf surface. After an incubation period in a climate-controlled chamber of 24-36 hours in the dark at 20°C and 75% RH, the leaf discs are kept at 20°C with 12 h of light / day and 75% RH. The activity of a compound is evaluated as the percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated control leaf discs (12-14 days after application). The following compounds resulted in at least 80% control of Phakopsora pachyrhizi at 200 ppm when compared with untreated controls under the same conditions, which showed extensive disease development: P-4, P-7, P-107, P-109, P-118, P-178, P-179. Example B10: Puccinia recondita f. sp. tritici / wheat / leaf disc dressing (Brown rust)
[00406] Wheat cv. Kanzler leaf segments are placed on agar in multi-well plates (24-well format). The leaf segments are inoculated with a spore suspension of the fungus. The plates are stored in the dark at 19 °C and 75% RH. The formulated test compound diluted in water is applied 1 day after inoculation. The Petition 870250055585, dated 01 / 07 / 2025, pages 245 / 501 232 / 236 leaf segments are incubated at 19 °C and 75% RH under a 12 h light / 12 h dark regime in a climate-controlled chamber, and the activity of a compound is evaluated as the percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated control leaf segments (6-8 days after application). The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm compared to the untreated control under the same conditions, which showed extensive disease development: P-4, P-91, P-93, P-107, P-109, P-118, P-127, P-156, P-160, P-162, P-178, P185. Example B11: Puccinia recondita f. sp. tritici / wheat / leaf disc preventative (Brown rust)
[00407] Wheat leaf segments cv. Kanzler are placed on agar in multi-well plates (24-well format) and sprayed with the formulated test compound diluted in water. Leaf discs are inoculated with a spore suspension of the fungus 1 day after application. The inoculated leaf segments are incubated at 19 °C and 75% RH under a 12 h light / 12 h dark regime in a climate-controlled chamber, and the activity of a compound is evaluated as a percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated control leaf segments (7-9 days after application). The following compounds gave at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm when compared to the untreated control under the same conditions, which showed Petition 870250055585, dated 01 / 07 / 2025, pages 246 / 501 233 / 236 extensive development of disease: P-1, P-4, P-6, P-7, P-21, P-22, P-23, P-25, P-26, P-27, P-29, P-30, P-31, P-45, P-47, P-55, P-56, P-57, P-62, P-70, P-76, P-79, P-80, P-88, P-91, P-92, P-93, P-102, P-105, P-107, P-108, P-109, P-110, P-112, P-114, P-117, P-118, P-119, P-120, P-123, P-125, P-127, P136, P-137, P-139, P-143, P-145, P-146, P-147, P-148, P-152, P-155, P-156, P-160, P-162, P-167, P-168, P-169, P-171, P172, P-173, P-174, P-176, P-177, P-178, P-179, P-180, P-181, P-182, P-183, P-184, P-185, P-187, P-188, P-190. Example B12: Magnaporthe grisea (Pyricularia oryzae) / rice / preventive in foliar discs (rice brushone)
[00408] Rice leaf segments cv. Ballila are placed on agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments are inoculated with a fungal spore suspension 2 days after application. The inoculated leaf segments are incubated at 22 °C and 80% RH under a 24 h light / dark regime followed by 12 h light / 12 h dark in a climate-controlled chamber, and the activity of a compound is evaluated as a percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated control leaf segments (5–7 days after application).The following compounds provided at least 80% control of Magnaporthe grisea at 200 ppm compared to an untreated control under the same conditions, which showed extensive disease development: P-4, P-6, P-7, P-10, P-20, P-21, P-22, P-23, P-25, P-26, P-27, P-29, P-30, P-32, P-33, P-35, P-44, P-45, P-46, P-47, P-49, P-52. Petition 870250055585, dated 01 / 07 / 2025, pages 247 / 501 234 / 236 P-55, P-57, P-60, P-61, P-62, P-65, P-66, P-67, P-68, P-69, P-70, P-71, P-74, P-76, P-87, P-88, P-89, P-90, P-91, P-93, P-94, P-95, P-102, P-103, P-104, P-105, P-107, P-108, P-109, P-110, P-111, P-112, P-113, P-117, P-118, P-119, P-120, P122, P-123, P-125, P-126, P-127, P-128, P-129, P-139, P-144, P-145, P-146, P-147, P-148, P-151, P-152, P-153, P-155, P156, P-159, P-160, P-162, P-164, P-177, P-180, P-185, P-189, P-192. Example B13 Pyrenophora teres / barley / leaf disc preventative (Net spot)
[00409] Leaf segments of barley cv. Hasso are placed on agar in a multi-well plate (24-well format) and sprayed with the formulated test compound diluted in water. The leaf segments are inoculated with a spore suspension of the fungus 2 days after application. The inoculated leaf segments are incubated at 20 °C and ur a 65% under a 12 h light / 12 h dark regime in a climate-controlled chamber, and the activity of a compound is evaluated as a percentage of disease control compared to no treatment when an appropriate level of disease damage appears on untreated control leaf segments (5-7 days after application). The following compounds provided at least 80% control of Pyrenophora teres at 200 ppm compared to the untreated control under the same conditions, which showed extensive disease development: P-4, P-6, P-7, P-10, P-22, P-26, P-29, P-44, P-45, P-57, P-62, P-76, P-93, P-94, P-102, P107, P-108, P-109, P-116, P-118, P-127, P-134, P-139, P-145, P-147, P-152, P-155, P-160, P-162, P-168, P-171, P-176, P178, P-179, P-180, P-185. Petition 870250055585, dated 01 / 07 / 2025, pages 248 / 501 235 / 236 Example B14: Sclerotinia sclerotiorum / liquid culture (white rot)
[00410] Mycelial fragments from a freshly cultivated liquid culture of the fungus are directly mixed into nutrient broth (potato broth and dextrose PDB). After placing a solution (DMSO) of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal material is added. The test plates are incubated at 24 °C and growth inhibition is determined photometrically 3-4 days after application. The following compounds resulted in at least 80% control of Sclerotinia sclerotiorum at 20 ppm when compared with untreated controls under the same conditions, which showed extensive disease development: P-4, P-10, P-19, P-44, P-67, P-74, P-107, P-108, P-109, P-122, P-123, P-139, P-145, P-147, P-152, P-157, P-160, P-162, P-180. Example B15: Mycosphaerella graminicola (Septoria tritici) / liquid culture (Septoria stain)
[00411] Cryogenically stored fungal conidia are directly mixed into nutrient broth (PDB potato dextrose broth). After placing a solution (DMSO) of the test compound in a microtiter plate (96-well format), the nutrient broth containing the fungal spores is added. The test plates are incubated at 24 °C and growth inhibition is determined photometrically 4-5 days after application. The following compounds gave control of at least 80% of Mycosphaerella graminicola at 20 ppm compared to the untreated control under the same conditions, which showed extensive growth. Petition 870250055585, dated 01 / 07 / 2025, pages 249 / 501 236 / 236 da doença: P-1, P-2, P-3, P-4, P-6, P-7, P-8, P-10, P-16, P18, P-19, P-20, P-22, P-23, P-25, P-26, P-27, P-28, P-29, P30, P-32, P-33, P-34, P-35, P-36, P-37, P-38, P-39, P-40, P41, P-43, P-44, P-45, P-46, P-47, P-55, P-56, P-57, P-58, P59, P-60, P-62, P-65, P-66, P-67, P-68, P-70, P-71, P-73, P74, P-75, P-76, P-79, P-83, P-91, P-93, P-94, P-96, P-102, P-104, P-107, P-108, P-109, P-110, P-111, P-112, P-113, P114, P-115, P-117, P-118, P-119, P-120, P-121, P-122, P-123, P-127, P-128, P-129, P-130, P-132, P-133, P-134, P-135, P139, P-140, P-144, P-145, P-146, P-147, P-148, P-151, P-152, P-153, P-155, P-157, P-160, P-162, P-168, P-170, P-171, P172, P-173, P-174, P-175, P-176, P-177, P-178, P-179, P-180, P-181, P-183, P-185, P-187, P-189, P-190, P-191.
Claims
1. Compound of formula (I): 1 5 R(I) characterized in that A is N or CH; R1 is hydrogen, cyano, formyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 haloalkylcarbonyl, C1-C6 alkoxyC1-C6 alkylcarbonyl, C3C6 cycloalkylcarbonyl, C1-C6 alkoxyC1-C3 alkoxycarbonyl, C1-C6 alkoxyoxallyl, C1-C6 alkoxycarbonylC1-C4 alkylC1-C6 alkoxycarbonyl, C2-C6 alkenyloxycarbonyl, or C2C6 alkynyloxycarbonyl; R2 is hydrogen; R3 is hydroxy, methoxy, ethoxy, isopropoxy, allyloxy, or methoxymethylcarbonyloxy; R4 is t-butyl, isopentyl, 2,2-dimethylpropyl, 1,1,2-trimethylpropyl, 1-methylcyclopropyl, 1methylcyclobutyl, 1-ethylcyclobutyl, 1isopropylcyclobutyl, 1-tertbutylcyclobutyl, 1cyclobutylcyclobutyl, 2,2-dimethylcyclobutyl, 1methylcyclopentyl, or spiro[3.4]octan-3-yl; R5 is C1-C8 hydroxyC1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C2 alkyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1, 2 or 3 heteroatoms individually selected from N, O Petition 870260058386, dated 16 / 06 / 2026, p. 11 / 18 2 / 4 and S, heterocyclyl, wherein the heterocyclyl is a non-aromatic monocyclic ring of 4, 5 or 6 members comprising 1, 2 or 3 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R9; R9 is halogen, cyano, C1-C4alkyl, C1-C4alkoxy, or C1-C4haloalkyl; or a salt thereof or an N-oxide.
2. Compound according to claim 1, characterized in that R1 is hydrogen, cyano, C1-C6 alkylcarbonyl, C1-C4 alkoxycarbonyl, C1-C4 haloalkylcarbonyl, C1-C4 alkoxyC1-C3 alkylcarbonyl, C3C6 cycloalkylcarbonyl, C1-C4 alkoxyC1-C2 alkoxycarbonyl, C2C4 alkenyloxycarbonyl, or C2-C4 alkenyloxycarbonyl.
3. Compound according to claim 1 or 2, characterized in that R5 is C1-C3 alkyl, hydroxyC1-C6 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1C2 alkyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, heterocyclyl, wherein heterocyclyl is a 5- or 6-membered non-aromatic monocyclic ring or a 9- to 10-membered non-aromatic bicyclic ring comprising 1 or 2 heteroatoms individually selected from N, O and S, and wherein the cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R9. Petition 870260058386, dated 06 / 16 / 2026, p. 12 / 18 3 / 4 4. Compound according to any one of claims 1 to 3, characterized in that R5 is C1-C4 alkyl, 2,3-dihydroxypropyl, C3-C4 cycloalkyl, cyclopropylmethyl, cyclobutylmethyl, phenyl, heteroaryl, wherein heteroaryl is a 5- or 6-membered aromatic monocyclic ring comprising 1 or 2 heteroatoms individually selected from N and S, heterocyclyl, wherein heterocyclyl is a 9- to 10-membered non-aromatic bicyclic ring comprising 1 or 2 oxygen atoms, and wherein the phenyl and heteroaryl moieties are each optionally substituted by 1, 2 or 3 substituents, which may be the same or different, selected from R9.
5. Compound according to any one of claims 1 to 4, characterized in that R5 is 2,3-dihydroxypropyl, cyclobutyl, cyclopropylmethyl, phenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 3-methylphenyl, 4-methylphenyl, 3-ethylphenyl, 3-methoxyphenyl, 3-cyanophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dimethylphenyl, 3,5-dimethoxyphenyl, 3fluoro-4-methylphenyl, 3-chloro-4-methylphenyl, 3-chloro-5-fluorophenyl, 4-chloro-3,5-difluorophenyl, 4-chloro-3-fluorophenyl, 4-chloro-3-methylphenyl, 3-cyano-5-methylphenyl, 3-cyano-5-fluorophenyl, 4-cyano-3-fluorophenyl, 3,4,5trifluorophenyl, 4-trifluoromethylphenyl, 3-fluoro-4(trifluoromethyl)phenyl, pyridin-4-yl, 2-fluoropyridin-4yl, 2-chloropyridin-4-yl, 2,6-difluoropyridin-4-yl, 2,6dichloropyridin-4-yl, pyridin-3-yl, 6-fluoropyridin-3-yl, 5-fluoropyridin-3-yl, 6-chloropyridin-3-yl, 5chloropyridin-3-yl, 5-(trifluoromethyl)-pyridin-3-yl, 2,6difluoro-3-iodopyridin-4-yl, isothiazol-4-yl,thiazol-2 Petition 870260058386, dated 06 / 16 / 2026, page 13 / 18 4 / 4 ila, pirimidin-5-ila, benzofuran-5-ila, 1-benzylindazole-6-ila, or 1,3-benzodioxol-5-ila., 6. Agrochemical composition, characterized in that it comprises an effective amount in terms of fungicides of a compound of formula (I), as defined in any one of claims 1 to 5.
7. Agrochemical composition, according to claim 6, characterized in that it further comprises at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.
8. Method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, characterized in that an effective amount in fungicidal terms of a compound of formula (I), as defined in any one of claims 1 to 5, or of a composition, as defined in claim 6 or 7, is applied to the plants, their parts or their locus.
9. Use of a compound of formula (I), as defined in any one of claims 1 to 5, characterized in that it is a fungicide, wherein said use excludes methods for treating the human or animal body by surgery or therapy.