Hydroxyisoxazolines and derivatives thereof, composition, use and method for controlling phytopathogenic fungi.

Abstract

Hydroxy-isoxazolines and derivatives thereof. This disclosure relates to the use of hydroxy-isoxazolines and derivatives thereof as fungicides. It also relates to new derivatives of hydroxy-isoxazolines, their use as fungicides, and compositions comprising them. Formula i

Description

"Hydroxyisoxazolines and derivatives thereof, composition, use and method for controlling phytopathogenic fungi" TECHNICAL FIELD

[001] The present invention relates to the use of hydroxy-isoxazolines and derivatives thereof as fungicides. It also relates to new derivatives of hydroxy-isoxazolines, their use as fungicides and compositions comprising them. BACKGROUND

[002] 3-Phenyl isoxazolines and their use as herbicides or insecticides are known from documents WO99 / 05130, WO2019 / 034602 and WO2009 / 051956. Isoxazole derivatives are known to be useful as crop protection agents to combat or prevent infestations of microorganisms. For example, document WO2015 / 129773 discloses isoxazole derivatives that can be used as fungicides. Document WO2006 / 031631 discloses substituted isoxazoles that can be used for the control of microbial pests, particularly fungal pests, in plants. More recently, hydroxy-isoxazoles have been disclosed as useful for controlling phytopathogenic fungi (WO2018 / 202487).

[003] Several fungicidal agents have been developed so far. However, the need remains for the development of new fungicidal compounds in order to meet the increasing environmental and economic demands placed on modern crop protection agents and compositions. This includes, for example, improvements in spectrum of action, safety profile, selectivity, application rate, residue formation, and favorable preparation capacity. It may also be desirable to have new compounds to prevent the emergence of fungicide resistance.

[004] The present invention provides novel fungicidal compounds that have advantages over known compounds and compositions in at least some of these respects. Petition 870250043647, dated 05 / 27 / 2025, page 5 / 149 2 / 125 SUMMARY

[005] The present invention relates to compounds of formula (I): (I) where R1, R2, X, m, ne Het are as recited in the present document, as well as their salts, N-oxides and solvates.

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

[007] The present invention relates to a method for controlling phytopathogenic fungi comprising the step of applying at least one compound of formula (I), as defined herein, or a composition as defined herein, to plants, plant parts, seeds, fruits or the soil in which the plants grow. DEFINITIONS

[008] The term “alkyl” as used in this document in the context of alkyl or alkylsulfonyl, alkylsulfinyl, alkylthio, alkylamino, for example, should preferably be understood as meaning alkylramified and not branched, meaning, for example, methyl, ethyl, n-propyl, / so-propyl, n-butyl, / so-butyl, tert-butyl, sec-butyl, pentyl, / so-pentyl, hexyl, heptyl, octyl, nonyl and decyl and isomers thereof. Petition 870250043647, dated 05 / 27 / 2025, p. 6 / 149 3 / 125

[009] The term “haloalkyl” as used in this document should preferably be understood to mean branched and unbranched alkyl, as defined above, in which one or more of the substituent hydrogens is substituted in the same or different ways with halogen. Particularly preferably, said haloalkyl is, for example, chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromobutyl, trifluoromethyl, iodoethyl, and isomers thereof.

[010] The term “alkoxy” as used in this document should preferably be understood as meaning branched and unbranched alkoxy, meaning, for example, methoxy, ethoxy, propyloxy, / so-propyloxy, butyloxy, / so-butyloxy, tert-butyloxy, sec-butyloxy, pentyloxy, / so-pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy and dodecyloxy and the isomers thereof.

[011] The term “haloalkoxy” as used in this document should preferably be understood as meaning branched and unbranched alkoxy, as defined above, in which one or more of the hydrogen substituents are substituted in the same or different ways with halogen, for example, chloromethoxy, fluoromethoxy, pentafluoroethoxy, fluoropropyloxy, difluoromethyloxy, trichloromethoxy, 2,2,2-trifluoroethoxy, bromobutyloxy, trifluoromethoxy, iodoethoxy, and isomers thereof.

[012] The term carbocyclyl, as used in this document, refers to a ring containing mono- or polycyclic carbon (fused, spiro or bridging), which may be saturated or partially unsaturated, having 3 to 10 carbon atoms in the ring or 3 to 7 carbon atoms. Examples of carbocyclyl include cycloalkyl and cycloalkenyl groups. Examples of saturated carbocyclyl, also referred to herein as “cycloalkyl”, include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl groups. Examples of partially unsaturated carbocyclyl groups include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl groups. Petition 870250043647, dated 05 / 27 / 2025, p. 7 / 149 4 / 125 cyclooctenyl, cyclononenyl, or cyclodecenyl, wherein the linkage of said cycloalkyl group to the rest of the molecule may be provided by a double or single bond.

[013] The term heterocycline, as used in this document, refers to three- to ten-membered, preferably three- to nine-membered, saturated or partially unsaturated heterocycles (including mono-, bi- or tricyclic heterocycles) containing one to four heteroatoms independently selected from the oxygen, nitrogen and sulfur groups. If the ring contains more than one oxygen atom, they are not directly adjacent. A polycyclic heterocycline may contain fused, spiro or bridging ring junctions. Examples of heterocyclyl group include, but are not limited to, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,5-thiazolidinediol, 2-imidazolidinediol, 4-imidazolidinediol, 1,2,4-oxadiazolidinediol-3-yl, 1,2,4-oxadiazolidinediol-5-yl, 1,2,4-thiadiazolidinediol3-yl, 1,2,4-thiadiazolidinediol-5-yl, 1,2,4-triazolidinediol-3-yl, 1,3,4-oxadiazolidinediol-2-yl, 1,3,4thiadiazolidinediol-2-yl, 1,3,4-triazolidinediol-2-yl, 2,3-di-hydrofur-2-yl, 2,3-di-hydrofur-3-yl, 2,4-di-hydrofur-2-yl, 2,4-di-hydrofur-3-yl, 2,3-di-hydrothien-2-yl, 2,3-di-hydrothyne-3-ila, 2,4-dihydrothyen-2-ila, 2,4-di-hydrothyne-3-ila, 2-pyrroline-2-ila, 2-pyrroline-3-ila, 3-pyrroline-2-ila, 3pyrroline-3-ila, 2-isoxazolin-3-ila, 3-isoxazolin-3-ila, 4-isoxazolin-3-ila, 2-isoxazolin-4-ila, 3-isoxazolin-4-ila, 4-isoxazolin-4-ila, 2-isoxazolin-5-ila, 3-isoxazolin-5-ila, 4-isoxazolin5-ila, 2-isothiazolin-3-ila, 3-isothiazolin-3-ila, 4-isothiazoline-3-ila, 2-isothiazoline-4-ila, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5yl, 2,3-di-hydropyrazole-1-yl, 2,3-di-hydropyrazole-2-yl, 2,3-di-hydropyrazole-3-yl, 2,3-dihydropyrazole-4-yl, 2,3-di-hydropyrazol-5-yl, 3,4-di-hydropyrazol-1-yl, 3,4-di-hydropyrazol-3-yl, 3,4-di-hydropyrazol-4-yl, 3,4-di-hydropyrazol-5-yl, 4,5-di-hydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-di-hydropyrazol-4-yl, 4,5-di-hydropyrazol-5-yl, 2,3-di-hydro, Petição 870250043647, de 05 / 27 / 2025, pág. 8 / 149 5 / 125 oxazol-2-ila, 2,3-di-hidro-oxazol-3-ila, 2,3-di-hidro-oxazol-4-ila, 2,3-di-hidro-oxazol-5ila, 3,4-di-hidro-oxazol-2-ila, 3,4-di-hidro-oxazol-3-ila, 3,4-di-hidro-oxazol-4-ila, 3,4-dihidro-oxazol-5-ila, 3,4-di-hidro-oxazol-2-ila, 3,4-di-hidro-oxazol-3-ila, 3,4-di-hidrooxazol-4-ila, 2-piperidinila, 3-piperidinila, 4-piperidinila, 1,3-dioxan-5-ila, 2-tetrahidropiranila, 4-Tetra-Hidropiranila, 2-Tetra-Hidrotienila, 3-Hexahidropiridazinila, 4hexahidopiridazinila, 2-Hexahidropirimidinila, 4-Hexahidropirimidinila, 5Hexahidropirimidinila, 2-piperazinila, 1,3,5-Hexahidrotriazin-2-ila, 1,2,4hexahidoratriazin-3-ila, indol-1-ila, indol-2-ila, indol-3-ila, indol-4-ila, indol-5-ila, indol-6ila, indol-7-ila, benzimidazol-1-ila, benzimidazol-2-ila, benzimidazol-4-ila, benzimidazol-5-ila, indazol-1-ila, indazol-3-ila, indazol-4-ila, indazol-5-ila, indazol-6-ila, indazol-7-ila, indazol-2-ila, 1-benzofuran-2-ila, 1-benzofuran-3-ila, 1-benzofuran-4-ila, 1-benzofuran-5-ila, 1-benzofuran-6-ila,1-benzothiophen-7-yl, 1-benzothiophen-2-yl, 1benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-benzothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl e 1,3-benzoxazol-7-yl, quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl. This definition also applies to heterocyclyl as part of a composite substituent, for example, heterocyclylalquila etc., unless defined elsewhere,

[014] The thermo halogênio or Hal, as used in this document, must be understood as meaning flavour, chlorine, bromine or iodine.

[015] The term halo in square brackets (e.g., C1-C6-(halo)alkyl”) designates the optional presence of one or more halogen substituents which may be the same or different. Petition 870250043647, dated 05 / 27 / 2025, p. 9 / 149 6 / 125

[016] The term alkenyl, as used in this document, should preferably be understood as meaning branched and unbranched alkenyl, for example, a vinyl group, propen-1-yl, propen-2-yl, but-1-en-1-yl, but-1-en-2-yl, but-2-en-1-yl, but-2-en-2-yl, but-1-en-3-yl, 2-methyl-prop-2-en-1-yl, or 2-methyl-prop-1en-1-yl.

[017] The term alkynyl, as used in this document, should preferably be understood as meaning branched and unbranched alkynyl, for example an ethynyl group, prop-1-yn-1-yl, but-1-yn-1-yl, but-2-yn-1-yl, or but-3-yn-1-yl.

[018] The term aryl as used herein refers to an aromatic hydrocarbon ring system comprising from 6 to 15 carbon atoms, or preferably from 6 to 12 carbon atoms. The ring system may be a monocyclic or polycyclic fused aromatic ring system (e.g., bicyclic or tricyclic). Examples of aryl include, but are not limited to, phenyl, azulenyl, naphthyl, and fluorenyl. It is further understood that when said aryl group is substituted with one or more substituents, said substituent(s) may be in any positions on said aryl ring(s). Specifically, if aryl is a phenyl group, the substituent(s) in question may occupy one or both ortho positions, one or both meta positions, or the para position, or any combination of these positions. This definition also applies to aryl as part of a compound substituent (e.g., aryloxy).

[019] The term “heteroaryl” as used in this document refers to an aromatic ring system containing 5 to 15 member atoms, or 5 to 12 member atoms, of which carbons and one or more heteroatoms, which may be identical or different, selected from O, N, and S. If the ring contains more than one oxygen atom, they are not directly adjacent. Heteroaryl can be monocyclic or polycyclic (e.g., bicyclic or tricyclic). A monocyclic heteroaryl can Petition 870250043647, dated 05 / 27 / 2025, p. 10 / 149 7 / 125 having 1 to 4 heteroatoms in the ring, while a polycyclic heteroaryl ring can have 1 to 10 heteroatoms. Bicyclic heteroaryl rings can contain 8 to 15, or 8 to 12 member atoms (carbon and heteroatoms). Monocyclic heteroaryl can contain 5 to 8 member atoms. Examples of heteroaryl include, but are not limited to, thienyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia-4H-pyrazolyl, etc., and benzo derivatives thereof, such as, for example, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzotriazolyl, indazolyl, indolyl, isoindolyl, etc.; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, etc., and benzo derivatives thereof, such as, for example, quinolinyl, isoquinolinyl, etc.; or azocinyl, indolizinyl, purinyl, etc., and benzo derivatives thereof; or cinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthpyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, or oxepinyl, etc. It is further understood that in the case where the said heteroaryl group is substituted by one or more substituents, the said substituent(s) may occupy any one or more positions in the said heteroaryl ring(s). In particular, if the heteroaryl is a pyridyl group, for example, the said substituent(s) may occupy any one or more of the positions 2, 3, 4, 5, and / or 6 relative to the nitrogen atom in the pyridine ring. This definition also applies to heteroaryl as part of a compound substituent (e.g., heteroaryloxy).

[020] As used in this document, the term “Ci-Cg”, for example, in the context of the definition of “C1-C6-alkyl”, or “C1-C6-alkoxy”, should be understood as meaning a group with a finite number of carbon atoms from 1 to 6, that is, 1, 2, 3, 4, 5 or 6 carbon atoms.

[021] The radical terms “acyclic” as used in the present document in expressions where acyclic radicals may be substituted” designates any of the acyclic groups recited in the paragraph preceding said expressions, or any Petition 870250043647, dated 05 / 27 / 2025, p. 11 / 149 8 / 125 acyclic portion of a composite group (e.g., the C1-C8-alkyl portion of a C1-C8-alkyl aryl group).

[022] The term “cyclic radicals”, as used in this document in the expressions “in which cyclic radicals can be substituted”, designates any of the cyclic groups, whether alicyclic or aromatic, mentioned in the paragraph preceding said expressions, or any cyclic portion of a composite group (for example, the aryl portion of aryl-C1-C6-alkyl).

[023] In a group containing an acyclic moiety and a cyclic moiety (for example, aryl-C1-C6-alkyl), each of these moieties can be substituted independently of the other.

[024] The term “labile group”, as used in this document, should be understood to mean a group that is displaced from a compound in a substitution or elimination reaction, for example a halogen atom, a trifluoromethanesulfonate (triflate) group, alkoxy, methanesulfonate, ptoluenesulfonate, etc. DETAILED DESCRIPTION ACTIVE INGREDIENTS

[025] The present invention relates to compounds of formula (I): (I) in which R1 is selected from the group consisting of hydrogen, C1-C8-alkyl, C3C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, -C1-C8-alkyl-aryl, -C1-C8-alkyl-C1 Petition 870250043647, dated 05 / 27 / 2025, p. 12 / 149 9 / 125 C8-alkoxy, -Si(Ci-C8-alkyl)3, -SiAryl(Ci-C8-alkyl)2, -Ci-C8-alkyl-C3-C8-cycloalkyl, aryl, heteroaryl, -Ci-C8-alkyl-heteroaryl, di-Ci-C8-alkylphosphate, -C(=O)Ra, C(=O)N(Ra)2, -Ci-C6-alkyl-OC(=O)Rae -Ci-C6-alkyl-C(=O)Ra, with Rasendo selected from the group consisting of hydrogen, amino, C1-Cio-alkyl, C1-C6haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, Ci-C8-alkoxy, Ci-C8-haloalkoxy, C1-C8-alkylsulfonyl, C1-C8-alkylamino, di-C1-C8-alkylamino, -C1-C6-alkyl-C1-C6-alkoxy, C3-C10-carbocyclyl, C3-C10-halocarbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, heterocycloxy, aryloxy and heteroaryloxy, wherein the R1 or R2 acyclic radicals may be substituted by one or more R1 substituents and wherein the R1 or R2 acyclic radicals may be substituted by one or more R1 substituents; X is an atom of hydrogen, fluorine, or chlorine; m is 0, i or 2; Het is a heteroarila of 5 members; n is 0, i, 2, 3 or 4; R2 is a substituent independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, sulfinyl, sulfonyl, amino, nitro, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-hydroxyalkenyl, C2-C6-cyanoalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C2-C6-hydroxyalkynyl, C2-C6-cyanoalkynyl, C1-C6-alkylsulfonyl, pentafluoro-X6-sulfaniyl, arylsulfaniyl, C1-C6-alkylsulfinyl, arylsulfinyl, C1-C6alkylsulfonyl, arylsulfonyl, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, C3-Cio-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, -Si(Ci-Ce-alkyl)3, -C(=O)R2i, -C(=O)OR2i, -C(=O)N(R2i)2, C(=O)N(OR2i)R2i, -C(=O)NR2iN(R2i)2, -C(=S)N(R2i)2, -C(=NR2i)R2i, Petition 870250043647, from 05 / 27 / 2025, p. 13 / 149 10 / 125 C(=NR21)N(R21)2, -C(=NOR21)R21, -N(R21)2, -NR21C(=O)OR21, -N(OR21)C(=O)OR21, NR21C(=O)N(R21)2, -NR21C(=O)R21, -N(OR21)R21, -N(OR21) -NR21C(=S)R21, NR21C(=S)N(R21)2, -NR21C(=NR21)R21, -OC(=O)R21, -OC(=O)N(R21)2, NR21S(=O)2R21, -N=CR21-N(R21)2, -N=CR21-N(R21)2, -R21, -R21, -S(=O)2N(R21)2, -P(=O)(OR21)2, -O-C1C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl, -C1-C6-(halo)alkyl-OC3-C10-carbocyl-Chalo-C 3- to 10-membered heterocycle, -C1-C6(halo)alkyl-O-, 3- to 10-membered heterocycle, -C1-C6-(halo)alkyl-aryl, -C1-C6(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl,-aryl -C1-C6-(halo)alkyl-OR21, -C1-C6-(halo)alkyl-C(=O)R21, -C1-C6-(halo)alkyl-C(=O)OR21, -C1-C6-(halo)alkylC(=O)N(R21)2, -C1-C6-(halo)alkyl-C(=O)R21,1 C(=O)NR21N(R21)2, -C1-C6-(halo)alkyl-C(=S)N(R21)2, C(=NR21)R21, -C1-C6-(halo)alkyl-C(=NR21)N(R21)2, -C1-C6-(halo)alquila-C1-C6-(halo)alquila-C1-C6-(halo)alquilaC(=NOH)R21, -C1-C6-(halo)alquila-N(R21)2, -C1-C6-(halo)alquila-NR21C(=O)OR21, -C1C6-(halo)alquila-N(OR21)C(=O)OR21, -C1-C6-(halo)alquila-NR21C(=O)N(R21)2, -C1-C6(halo)alquila-NR21C(=O)R21, -C1-C6-(halo)alquila-N(OR21)C(=O)R21, -C1-C6(halo)alquila-NR21C(=S)R21, -C1-C6-(halo)alquila-NR21C(=S)N(R21)2, -C1-C6(halo)alquila-NR21C(=NR21)R21, -C1-C6-(halo)alquila-OC(=O)R21, -C1-C6-(halo)alquilaOC(=O)N(R21)2, -C1-C6-(halo)alquila-NR21S(=O)2R21, -C1-C6-(halo)alquila-N=CR21N(R21)2, -C1-C6-(halo)alquila-SR21, -C1-C6-(halo)alquila-S(=O)R21, -C1-C6(halo)alquila-S(=O)OR21, -C1-C6-(halo)alquila-S(=O)2R21, -C1-C6-(halo)alquilaS(=O)2OR21, -C1-C6-(halo)alquila-S(=O)2N(R21)2 and -C1-C6-(halo)alquila-P(=O)(OR21)2, where R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl and -C1-C6-(halo)alkyl-aryl, wherein the acyclic radicals R2 and R21 may be substituted by one or more R22a substituents and the cyclic radicals R2 and R21 may be substituted by one or more R22c substituents. Petition 870250043647, dated 05 / 27 / 2025, p. 14 / 149 11 / 125 R1a, R22a, R1c and R22c are independently selected from the group consisting of halogen atom, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-X6-sulfanyl, formyl, carbamoyl, carbamate, C1-C6-alkyl, C3-C7cycloalkyl, C1-C6-haloalkyl, C3-C8-halocycloalkyl, C2-C6-(halo)alkenyl, C2-C6(halo)alkynyl, C1-C6-alkylamino, di-C1-C6-alkylamino, -Si(C1-C6-alkyl)3, C1-C6(halo)alkoxyC1-C6-(halo)alkylsulfonyl, C1-C6-(halo)alkylcarbonyl, C1-C6alkylcarbamoyl, di-C1-C6-alkylcarbamoyl, C1-C6-(halo)alkoxycarbonyl, aryloxy, C1-C6-(halo)alkylcarbonyloxy, C1-C6-(halo)alkylcarbonylamino, C1-C8(halo)alkylsulfonyl, C1-C8-(halo)alkylsulfinyl, C1-C8-(halo)alkylsulfonyl, C1-C8alkylsulfonylamino, C1-C8-haloalkylsulfonylamino, sulfamoyl, C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl; provided that Het is not 3-ethyl-1,2,4-oxadiazol-5-yl; and provided that the compound of formula (I) is not: 3-[4-(1 -methyl-1 H-pyrazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(1H-pyrazol-3-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(1 H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-oxa,5-di-2-5 3-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(1,2-oxazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(1 -ethyl-1 H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(1 -methyl-1 H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-3-di-4-hydroxa- -ethyl-1 H-pyrazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(2-chloro-1-methyl-1 H-imidazol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[3-fluoro-4-(1H-imidazol-1-yl)phenyl]-5-(trifluoromethyl)-4,5-e-di-2-hydroxa- 3-[4-(2,5-dimethyl-1 H-pyrrol-1 -yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol. The excluded compounds are disclosed in document WO2019 / 122393.

[026] The invention encompasses pure stereoisomers of the compound of formula (I) and any mixture of these isomers.

[027] Compounds resulting from combinations that go against natural laws and that a person skilled in the art would exclude are not included in this document. Petition 870250043647, dated 05 / 27 / 2025, p. 15 / 149 12 / 125 therefore, based on their specialized knowledge. For example, ring structures with three or more adjacent oxygen atoms are excluded.

[028] Depending on the nature of the substituents, the compound of formula (I) may be present in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Consequently, the invention covers both pure stereoisomers and any mixture of these isomers. When a compound may be present in two or more tautomer forms in equilibrium, reference to the compound by means of a tautomer description should be considered as including all tautomer forms.

[029] Any of the compounds of the present invention may also exist in one or more geometric isomeric forms depending on the number of double bonds in the compound. Geometric isomers by nature of the substituents on a double bond or a ring may be present in cis (= Z-) or trans (= E-) form. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions.

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

[031] Depending on the nature of the substituents, the compound of formula (I) may be present in the form of the free compound and / or a salt thereof, such as an agrochemically active salt.

[032] Agrochemically active salts include acid addition salts of inorganic and organic acids, as well as salts of common bases. Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acid salts, such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, carbonic acid. Petition 870250043647, dated 05 / 27 / 2025, page 16 / 149 13 / 125 and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or di-unsaturated fatty acids with 6 to 20 carbon atoms, alkyl sulfuric monoesters, alkyl sulfonic acids (sulfonic acids with linear or branched alkyl radicals with 1 to 20 carbon atoms), aryl sulfonic acids or aryl disulfonic acids (aromatic radicals, such as phenyl and naphthalyl, carrying one or two sulfonic acid groups), alkyl phosphonic acids (phosphonic acids with linear or branched alkyl radicals with 1 to 20 carbon atoms), acids arylphosphonic acids or aryl diphosphonic acids (aromatic radicals, such as phenyl and naphthalyl, which carry one or two phosphonic acid radicals), where the alkyl and aryl radicals may contain other substituents, for example,p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxy benzoic acid, etc.,

[033] The solvates of compounds of formula (I) or their salts are stoichiometric compositions of the compounds with solvents.

[034] Compounds of formula (I) can exist in multiple crystalline and / or amorphous forms. Crystalline forms include non-solvated crystalline forms, solvates and hydrates.

[035] The compounds of formula (I) are referred to here as active ingredients.

[036] In some embodiments, in formula (I) above, (I), R1 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, -C1-Ce-alkyl-aryl, -C1-Ce-alkyl-C1-Ce-alkoxy, -Si(C1-Ce-alkyl)3, SiAryl(C1-C6-alkyl)2, -C(=O)Ra, -C(=O)N(Ra)2, -C1-C6-alkyl-OC(=O)Ra and -C1-C6alkyl-C(=O)Ra, with Ra being selected from the group consisting of C1-Cw-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, -C1-C6-alkyl-C1-C6 Petition 870250043647, dated 05 / 27 / 2025, p. 17 / 149 14 / 125 alkoxy, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl and heteroaryl, wherein the R1 or Raacyclic or cyclic radicals may be substituted as described in this document.

[037] In some embodiments, in formula (I) above, (I), R1 is selected from the group consisting of hydrogen, C1-Cw-alkyl, -Si(C1-C6-alkyl)3, -C(=O)Rae - C1C6-alkyl-C(=O)Ra, with Ra being selected from the group consisting of C1-C6 alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-alkoxy, C3-C10 carbocyclyl, aryl and heteroaryl. The acyclic or cyclic R1 or Ra radicals may be substituted as described in this document.

[038] In some embodiments, in formula (I) above, R1 is selected from the group consisting of hydrogen, C1-C6-alkyl and -C(=O)Raem where Ra is a C1-C6-alkyl (e.g., methyl). The acyclic or cyclic R1 or Ra radicals may be substituted as described in this document.

[039] In some embodiments, in formula (I) above, R1 is a hydrogen atom.

[040] In some forms, in formula (I) above, m represents 0 or 1.

[041] In some modalities, in formula (I) above, m represents 1.

[042] In some modalities, in formula (I) above, m represents 0.

[043] In some embodiments, in formula (I) above, Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl. Het may be attached to the phenyl group via one of the carbon ring atoms or via a member of the Het nitrogen ring (if present). Examples of 5-membered heteroaryl groups that are attached to the phenyl ring through one of the carbon ring members are fur-2-yl, fur-3-yl, thien-2-yl, thien-3-yl, pyrrole-2-yl, pyrrole-3-yl, isoxazol3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, pyrazol3-yl, pyrazol-4-yl, pyrazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, Petition 870250043647, dated 05 / 27 / 2025, p. 18 / 149 15 / 125 tiazol-4-ila, tiazol-5-ila, imidazol-2-ila, imidazol-4-ila, 1,2,4-oxadiazol-3-ila, 1,2,4oxadiazol-5-ila, 1,2,4-tiadiazol-3-ila, 1,2,4-tiadiazol-5-ila, 1,2,4-triazol-3-ila, 1,3,4oxadiazol-2-ila, 1,3,4-tiadiazol-2-ila, 1,3,4-triazol-2-il e tetrazol-5-il. Examples of 5-membered heteroaryl groups that are fixed to the phenyl ring through a member of the nitrogen ring are pyrrol-1-ila, pyrazol-1-ila, 1,2,4-triazol-1-ila, imidazol-1-ila, 1,2,3-triazol-1-ila and 1,3,4-triazol-1-ila.

[044] In some embodiments, in formula (I) above, it is selected from the group consisting of furila, thienila, isoxazolila, pyrazolila, thiazolila, imidazolila, oxadiazolila, triazolila and tetrazoila.

[045] In some embodiments, in formula (I) above, it is selected from the group consisting of furila, thienila, pyrrolila, isoxazolila, isotiazolila, pyrazolila, oxazolila, tiazolila, oxadiazolila, tiadiazolila, triazolila and tetrazolila.

[046] In some embodiments, in formula (I) above, Het is selected from the group consisting of pyrazolyl, isothiazolyl and oxadiazolyl.

[047] In some embodiments, in formula (I) above, X is a fluorine or chlorine atom.

[048] In some embodiments, in formula (I) above, X is a fluorine atom.

[049] In some embodiments, in formula (I) above, X is a hydrogen atom.

[050] In some embodiments, in formula (I) above, X is a chlorine atom.

[051] In some embodiments, in formula (I) above, R1 is a hydrogen atom and X is a fluorine atom or a chlorine atom.

[052] In some forms, in formula (I) above, n represents 0, 1 or 2.

[053] In some forms, in formula (I) above, n represents 0 or 1.

[054] In some embodiments, in the above formula, (I), R2 is independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-Petição 870250043647, dated 27 / 05 / 2025, page 19 / 149 16 / 125 cyanoalkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylamino, di-Ci-C6-alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-Calkyl-C6 arylsulfanyl, Ci-C6-alkylsulfinyl, arylsulfinyl, Ci-Ce-alkylsulfonyl, arylsulfonyl, C3-Cio-carbocyclyl, 3- to i0-membered heterocycl, aryl, heteroaryl, C3-Cio-carbocycloxy, membros aryloxy heterocyloxy C(=O)R21, -C(=O)OR21, -C(=O)N(R21)2, -C(=O)N(OR21)R21, -C(=O)NR21N(R21)2, C(=S)N(R21)2, -C(=NOR21)2,R21 -NR21C(=O)OR21, -NR21C(=O)N(R21)2, NR21C(=O)R21, -NR21C(=S)R21, -NR21C(=S)N(R21)2, -NR21C(=NR21)R21,=R -OC -OC(=O)N(R21)2, -NR21S(=O)2R21, -S(=O)2R21, -S(=O)2N(R21)2, -O-Ci-Ce-(halo)alkylaryl, -Ci-C6-(halo)cyclyl,-C3-carbo -Ci-Ce-(halo)alkyl-O-C3-Cy0carbocyclyl -Ci-C6-(halo)alkyl- 3- to 10-membered heterocycle, -Ci-Ce-(halo)alkylO-, 3- to 10-membered heterocycle,6--Cal-cyharyl-Ci-Ce-(halo)alkylheteroaryl, -Ci-C6-(halo)alkyl-heteroaryloxy, -Ci-C6-(halo)alkyl-OR21, -Ci-Ce(halo)alkyl-C(=O)R21, -Ci-Ce-(halo)alkyl-C(=O)R21, -Ci-Ce-(halo)alkyl-ORC(=O)21 -Ci-Ce-(halo)alkylC(=O)N(R21)2, -Ci-Ce-(halo)alkyla-C(=O)N(OR21)R21, -Ci-Ce-(halo)alkylaC(=O)NR21N(R21)2, -C1-Ce-(halo)alkylaC(=O)N(R21)2, -C1-Ce-(halo)alkyl-N(R21)2, Ci-Ce-(halo)alkyl-NR21C(=O)OR21, -Ci-Ce-(halo)alkyl-NR21C(=O)N(R21)2, -Ci-Ce(halo)alkyl-NR21C(,=O) -C1-Ce-(halo)alkyl-NR21C(=S)R21, -C1-Ce-(halo)alkylNR21C(=S)N(R21)2, -Ci-Ce-(halo)alkyla-OC(=O)R21, -Ci-Ce-(halo)alkyl-OC(=O)R2 -C1-Ce-(halo)alkyl-NR21S(=O)2R21, -C1-Ce-(halo)alkyl-SR21, -C1Ce-(halo)alkyl-S(=O)R21, -C1-Ce-(halo)alkyla-S(=O)OR21, -C1-Ce-(Halo)alkyl-S(=O)OR21, -C1-Ce-(O)2(S2) -Ci-Ce-(halo)alkyla-S(=O)2OR21e -Ci-Ce-(halo)alkyla-S(=O)2N(R21)2 in which R21é described in this paper, preferably R21é independently selected from the group consisting of hydrogen, Cy-Ce-Calquila,Aryl and -Ci-Ce(halo)alkyl-aryl. The acyclic R2 or R21 and cyclic R2 and R21 radicals may be substituted as described in this document. Petition 870250043647, dated 05 / 27 / 2025, p. 20 / 149 17 / 125

[055] In some embodiments, in the above formula, (I), R2 is independently selected from the group consisting of halogen, cyano, C1-C6 alkyl (e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl), C1-C6 haloalkyl (e.g. trifluoromethyl, difluoromethyl), C1-C6 alkoxy (e.g. methoxy), C1-C6 alkylamino (e.g. methylamino), di-C1-C6 alkylamino (e.g. dimethylamino), C1-C6 alkenyl (e.g. allyl), C2-C6 alkynyl, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C1-C6 alkylsulfanyl (e.g. methylsulfanyl), C3-C10 carbocyclyl (preferably C3-C6 carbocyclyl, e.g. cyclopropyl, cyclopentyl), aryl (e.g., phenyl), heteroaryl (preferably 5- or 6-membered heteroaryl comprising one or two heteroatoms, e.g., thienyl, pyridinyl), -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-C1-Ce-(halo)alkyl-aryl, -C1-C6(halo)alkyl-C3-C10-carbocyclyl, -C1-C6-(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-aryl,-C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21 and -C1-C6-(halo)alkyl-C(=O)OR21 with R21 being as described herein, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl. The acyclic or cyclic radicals R2 and R21 may be substituted as described herein, preferably substituted with halogen or C1-C6-(halo)alkyl.

[056] Examples of suitable -C(=O)R21 radicals include -C(=O)-C1-C6(halo)alkyl (e.g., methyl carbonyl).

[057] Examples of suitable -C(=O)OR21 radicals include -C(=O)-O-C1-C6(halo)alkyl (e.g., tert-butyl oxycarbonyl).

[058] Examples of suitable -N(R21)2 radicals include -NH-C1-C6(halo)alkyl-aryl (preferably -NH-C1-C6-(halo)alkyl-phenyl, for example, -NHCH2-phenyl).

[059] Examples of suitable -O-C1-C6-(halo)alkyl-aryl include -O-C1-C6(halo)alkyl-phenyl (e.g., -O-CH2-phenyl). Petition 870250043647, dated 05 / 27 / 2025, page 21 / 149 18 / 125

[060] Examples of suitable -C1-C6-(halo)alkyl-aryl include -C1-C6(halo)alkyl-phenyl (e.g., -CH2-phenyl).

[061] Examples of suitable -C1-C6-(halo)alkyl-heteroaryl include C1-C6(halo)alkyl-heteroaryl wherein said heteroaryl is a 5- or 6-membered heteroaryl comprising one or two heteroatoms (e.g., thienyl, pyridinyl).

[062] Examples of suitable -C1-C6-(halo)alkyl-OR21 include -C1-C6(halo)alkyl-O-C1-C6-(halo)alkyl, for example, methoxyethyl).

[063] Examples of suitable -C1-C6-(halo)alkyl-C(=O)OR21 include C1C6-(halo)alkyl-C(=O)OH and C1-C6-(halo)alkyl-C(=O)-OC1-C6-(halo)alkyl.

[064] In some embodiments, in the above formula (I), R2 is independently selected from the group consisting of fluorine, chlorine, cyanomethyl, ethyl, propyl, isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridinyl, -C(=O)H, methylcarbonyl, tert-butyloxycarbonyl, -CH2-cyclopropyl, -CH2-(N-morpholinyl), -CH2-phenyl(benzyl), -CH2-thienyl, -CH2-pyridinyl, methoxyethyl, -CH2-C(=O)OH, -CH2-C(=O)O-methyl and -CH2C(=O)O-ethyl, wherein acyclic and cyclic R2 radicals may be substituted by halogen or C1-C6-(halo)alkyl. In particular, phenyl radicals can be replaced by halogens, for example, fluorine or chlorine.

[065] In some embodiments, in formula (I) above, (I), R2 is independently selected from the group consisting of C1-C6-haloalkyl, such as trifluoromethyl and difluoromethyl.

[066] In some embodiments, in formula (I) above, Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl.

[067] In some of the aforementioned embodiments, compounds are excluded in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present; i.e., if n = 1) is methyl or ethyl. Petition 870250043647, dated 05 / 27 / 2025, p. 22 / 149 19 / 125

[068] In some other of the aforementioned embodiments, compounds are excluded in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[069] In some other embodiments mentioned, compounds are excluded wherein Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[070] In some other embodiments mentioned, compounds are excluded in which Het is pyrazolyl or oxadiazolyl, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[071] In some forms, in formula (I) above, n is 1, 2, 3 or 4, preferably 1 or 2,

[072] Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl, and

[073] R2 is independently selected from the group consisting of halogen, cyano, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkylsulfonyl, Ca-Cw-carbocyclyl, aryl, heteroaryl, -C(=O)R21, C(=O)OR21, -N(R21)2, -O-C1-Ce-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl, -C1-C6-(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6(halo)alkyl-aryl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21 and -C1-C6(halo)alkyl-C(=O)OR21 with R21 being as described in the present document and wherein the acyclic or cyclic radicals R2 and R21 may be substituted as recited in claim 1. Preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, and the radicals R2 and R21 may be substituted by halogen or C1-C6-(halo)alkyl.

[074] In some forms, in formula (I) above, n is 1, 2, 3 or 4, preferably 1 or 2, Petition 870250043647, dated 05 / 27 / 2025, p. 23 / 149 20 / 125

[075] Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl, and

[076] R2 is independently selected from the group consisting of fluorine, chlorine, cyano, propyl, isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridinyl, -C(=O)H, methylcarbonyl, tert-butyloxycarbonyl, -CH2-cyclopropyl, -CH2-(N-morpholinyl), -CH2-phenyl (benzyl), -CH2-thienyl, -CH2-pyridinyl, methoxyethyl, -CH2-C(=O)OH, -CH2-C(=O)O-methyl and -CH2C(=O)O-ethyl, wherein the acyclic and cyclic R2 radicals may be substituted by halogen or C1-C6-(halo)alkyl. In particular, phenyl radicals can be replaced by halogens, for example, fluorine or chlorine.

[077] The definitions of R1, R2, X, m, ne Het specified above can be combined in various ways to provide subclasses of compounds according to the invention.

[078] Non-limiting examples of compound subclasses include the subclasses described in this document below.

[079] In some embodiments (referred to in this document as embodiment Ia), the compounds of the present invention are compounds of formula (I) in which R1 is selected from the group consisting of hydrogen, C1-C8-alkyl, C3C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, -C1-C8-alkyl-aryl, -C1-C8-alkyl-C1C8-alkoxy, -Si(C1-C8-alkyl)3, -SiAryl(C1-C8-alkyl)2, -C1-C8-alkyl-C3-C8-cycloalkyl, Petition 870250043647, dated 05 / 27 / 2025, p. 24 / 149 21 / 125 aryl, heteroaryl, -Ci-C8-alkyl- heteroaryl, di-Ci-C8-alkylphosphate, -C(=O)Ra, C(=O)N(Ra)2, -Ci-C6-alkyl-OC(=O)Rae -Ci-C6-alkyl-C(=O)Ra, with Rasendo selected from the group consisting of hydrogen, amino, C1-Cio-alkyl, C1-C6haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylsulfonyl, C1-C8-alkylamino, di-C1-C8alkylamino, -Ci-C6-alkyl-Ci-C6-alkoxy, C3-C10-carbocyclyl, C3-C10-halocarbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, heterocycloxy, aryloxy and heteroaryloxy, wherein the R1a or R1acyclic radicals may be substituted by one or more R1c substituents; m is 0 or 1;

[080] Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl; X is an atom of hydrogen, fluorine, or chlorine; n is 0, i or 2, preferably 0 or i; R2 é independently selecionado do grupo que consiste em halogênio, ciano, hidróxi, sulfanila, amino, Ci-C6-alquila, Ci-C6-haloalquila, Ci-C6-hidroxialquila, Ci-C6-cianoalquila, Ci-C6-alcóxi, Ci-C6-haloalcóxi, Ci-C6-alquilamino, di-Ci-C6alquilamino, C2-C6-alquenila, C2-C6-haloalquenila, C2-C6-alquinila, C2-C6haloalquinila, Ci-C6-alquilsulfonila, arilsulfanila, Ci-C6-alquilsulfinila, arilsulfinila, CiC6-alquilsulfonila, arilsulfonila, C3-Ci0-carbociclila, heterocyclyl of 3 to 10 members, aryla, heteroaryl, C3-Ci0-carbociclilóxi, heterociclilóxi of 3 to 10 members, arylóxi, heteroarylóxi, -C(=O)R2i, -C(=O)OR2i, -C(=O)N(R2i)2, -C(=O)N(OR2i)R2i, C(=O)NR21N(R21)2, -C(=S)N(R21)2, -C(=NOR21)R21, -N(R21)2, -NR21C(=O)OR21, NR2iC(=O)N(R2i)2, -NR2iC(=O)R2i, -NR2iC(=S)R2i, -NR2iC(=S)N(R2i)2, Petition 870250043647, 05 / 27 / 2025, pág. 25 / 149 22 / 125 NR21C(=NR21)R21, -OC(=O)R21, -OC(=O)N(R21)2, -NR21S(=O)2R21, -S(=O)2R21, S(=O)2N(R21)2, -O-C1-C6-(halo)alquila-aryl, -C1-C6-(halo)alquila-C3-C10-carbocyclyl, C1-C6-(halo)alquila-O-C3-C10-carbocyclyl -C1-C6-(halo)alquila- heterociclila de 3 a 10 membris, -C1-C6-(halo)alquila-O-, heterociclila de 3 a 10 membris, -C1-C6 (halo)alquila-aryl, -C1-C6-(halo)alquila-heteroaryla, -C1-C6-(halo)alquila-heteroarylóxi, C1-C6-(halo)alquila-OR21, -C1-C6-(halo)alquila-C(=O)R21, C(=O)OR21, -C1-C6-(halo)alquila-C(=O)N(R21)2, C(=O)N(OR21)R21, -C1-C6-(halo)alquila-C(=O)NR21N(R21)2, -C1-C6-(halo)alkyl-C1-C6-(halo)alkyl-C1-C6-(halo)alkylC(=S)N(R21)2, -C1-C6-(halo)alkyl-N(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)OR21, -C1C6-(halo)alkyl-NR21C(=O)N(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)R21, -C1-C6(halo)alkyl-NR21C(=S)R21, -C1-C6-(halo)alkyl-NR21C(=S)N(R21)2, -C1-C6(halo)alkyl-OC(=O)R21, -C1-C6-(halo)alkyl-OC(=O)N(R21)2, -C1-C6-(halo)alkylNR21S(=O)2R21, -C1-C6-(halo)alkyl-SR21, -C1-C6-(halo)alkyl-S(=O)R21, -C1-C6(halo)alkyl-S(=O)OR21, -C1-C6-(halo)alkyl-S(=O)2R21, -C1-C6-(halo)alkylS(=O)2OR21 and -C1-C6-(halo)alkyl-S(=O)2N(R21)2 wherein R21 is as described herein, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, wherein the acyclic radicals R2 and R21 can be substituted by one or more R22a substituents and the cyclic radicals R2 and R21 can be substituted by one or more R22c substituents,R22ae R22cs, as described in this document.

[081] In some embodiments, according to embodiment (Ia), R2 is independently selected from the group consisting of halogen, cyano, C1-C6 alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6 alkylsulfonyl, C3-C10-carbocyclyl, aryl, heteroaryl, -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl, -C1-C6(halo)alkyl- 3 to 10 membered heterocyclyl, -C1-C6-(halo)alkyl-aryl, -C1-C6 Petition 870250043647, dated 05 / 27 / 2025, page 26 / 149 23 / 125 (halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21 and -C1-C6-(halo)alkyl-C(=O)OR21 with R21 being as described in the present document and the acyclic or cyclic radicals R2 and R21 may be substituted as recited in claim 1. Preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, and the radicals R2 and R21 may be substituted by halogen or C1-C6-(halo)alkyl.

[082] In some embodiments, in the above formula (I), R2 is independently selected from the group consisting of fluorine, chlorine, cyanomethyl, ethyl, propyl, isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridinyl, -C(=O)H, methylcarbonyl, tert-butyloxycarbonyl, -CH2-cyclopropyl, -CH2-(N-morpholinyl), -CH2-phenyl(benzyl), -CH2-thienyl, -CH2-pyridinyl, methoxyethyl, -CH2-C(=O)OH, -CH2-C(=O)O-methyl and -CH2C(=O)O-ethyl, wherein acyclic and cyclic R2 radicals may be substituted by halogen or C1-C6-(halo)alkyl. In particular, phenyl radicals can be replaced by halogens, for example, fluorine or chlorine.

[083] In some embodiments, according to embodiment (Ia), Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl. In some of said embodiments, compounds are excluded in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is methyl or ethyl. In some other of said embodiments, compounds are excluded in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C1-C6-alkyl. In some other embodiments, compounds are excluded where Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C1-C6-alkyl. In some other embodiments, compounds are excluded where Het is pyrazolyl or oxadiazolyl, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[084] In some modalities, according to the modality (Ia), Petition 870250043647, 05 / 27 / 2025, p. 27 / 1 24 / 125 is not 1 or 2,

[085] It is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl, e R2 independently selected from the group consisting of halogen, cyano, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkylsulfonyl, C3-C10-carbocyclyl, aryl, heteroaryl, -C(=O)R21, C(=O)OR21, -N(R21)2, -O-C1-Ce-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10carbocyclyl, -C1-C6-(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6(halo)alkyl-aryl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21 and -C1-C6(halo)alkyl-C(=O)OR21 with R21 being as described herein and wherein the acyclic or cyclic radicals R2 and R21 may be substituted as described herein. Preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkylaryl, and the radicals R2 and R21 may be substituted by halogen or C1-C6(halo)alkyl.

[086] In some modalities, according to the modality (Ia), n is 1 or 2, Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl, and R2 is independently selected from the group consisting of fluorine, chlorine, cyano, propyl, isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridinyl, -C(=O)H, methylcarbonyl, tert-butyloxycarbonyl, -CH2-cyclopropyl, -CH2-(N-morpholinyl), -CH2-phenyl (benzyl), -CH2-thienyl, CH2-pyridinyl, methoxyethyl, -CH2-C(=O)OH, -CH2-C(=O)O-methyl and -CH2-C(=O)O-ethyl. Petition 870250043647, dated 05 / 27 / 2025, p. 28 / 149 25 / 125 wherein the acyclic and cyclic R2 radicals can be substituted by halogen or C1-C6-(halo)alkyl. In particular, the phenyl radicals can be substituted by halogen, for example, fluorine or chlorine.

[087] In some embodiments (referred to in this document as embodiment Ia), the compounds of the present invention are compounds of formula (I) in which R1 is selected from the group consisting of hydrogen, C1-C6-alkyl, Si(C1-C6-alkyl)3, -C(=O)Ra, and -C1-C6-alkyl-C(=O)Ra, with Ra being selected from the group consisting of C1-C10-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, -C1-C6-alkylC1-C6-alkoxy, C3-C10-carbocyclyl, aryl and heteroaryl, wherein the R1 or Ra acyclic radicals may be substituted by one or more substituents R1a and wherein the R1 or Ra cyclic radicals may be substituted by one or more substituents R1c; R1a and R1c being as disclosed in this document, m is 0 or 1; Het is selected from the group consisting of furyl, thienyl, isoxazolyl, pyrazolyl, thiazolyl, imidazolyl, oxadiazolyl, triazolyl, and tetrazolyl; X is an atom of hydrogen, fluorine, or chlorine; n is 0, 1 or 2, preferably 0 or 1; R2 is independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-Alkoxy, C1-C6-alkylamino ... 26 / 125 alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6 haloalkynyl, Ci-C6-alkylsulfonyl, arylsulfanyl, Ci-C6-alkylsulfinyl, arylsulfanyl, CiC6-alkylsulfonyl, arylsulfonyl, C3-Cio-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, C3-C10-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, -C(=O)R21, -C(=O)OR21, -C(=O)R21, -C(=O -C(=O)N(OR21)R21, C(=O)NR21N(R21)2, -C(=S)N(R21)2, -C(=NOR21)R21, -N(R21)2, -NR21C(=O)OR21, NR21C(=O)N(R21)2, -NR21C(=O -NR21C(=S)R21, -NR21C(=S)N(R21)2, NR21C(=NR21)R21, -OC(=O)R21, -OC(=O)N(R21)2, -NR21S(=O)2R21, -S(=O)2R21, S(=O)2N(R21)2 -O-C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl, C1-C6-(halo)alkyl-O-C3-C10-carbocyclyl -C1-C6-(halo)alkyl- 30-membered heterocycle, -C1-C6-(halo)alkyl-O-, 3- to 10-membered heterocycle, -C1-C6 (halo)alkyl-aryl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-heteroaryloxy, C1-C6-(halo)alkyl-OR-C1-C6-(halo)alkyl-C(=O)R21, C(=O)OR21, -C1-C6-(halo)alkyl-C(=O)N(R21)2, C(=O)N(OR21)R21, -C1-C6-(halo)alkyl-C(=O)NR21N(R21)2, -C1-C6-(halo)alkyl-C1-C6-(halo)alkyl-C1-C6-(halo)alkylC(=S)N(R21)2, -C1-C6-(halo)alkyl-N(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)OR21, -C1C6-(halo)alkyl-NR21C(=O)N(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)R21, -C1-C6(halo)alkyl-NR21C(=S)R21, -C1-C6-(halo)alkyl-NR21C(=S)N(R21)2, -C1-C6(halo)alkyl-OC(=O)R21, -C1-C6-(halo)alkyl-OC(=O)N(R21)2, -C1-Ce-(halo)alkylNR21S(=O)2R21, -C1-C6-(halo)alkyl-SR21, -C1-C6-(halo)alkyl-S(=O)R21, -C1-C6(halo)alkyl-S(=O)OR21, -C1-C6-(halo)alkyl-S(=O)2R21, -C1-C6-(halo)alkylS(=O)2OR21 and -C1-C6-(halo)alkyl-S(=O)2N(R21)2 wherein R21 is as described herein, wherein R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, wherein the acyclic radicals R2 and R21 may be substituted by one or more R22a substituents and the cyclic radicals R2 and R21 may be substituted by one or more R22c, R22a and R22c substituents as described in this document. Petition 870250043647, dated 05 / 27 / 2025, p. 30 / 149 27 / 125

[088] In some embodiments (referred to in this document as embodiment Ia), the compounds of the present invention are compounds of formula (I) in which R1 is selected from the group consisting of hydrogen, C1-C6-alkyl and C(=O)Ra, where Ra is a C1-C6-alkyl (e.g., methyl); m is 0 or 1; Het is selected from the group consisting of furyl, thienyl, isoxazolyl, pyrazolyl, thiazolyl, imidazolyl, oxadiazolyl, triazolyl, and tetrazolyl; X is an atom of hydrogen, fluorine, or chlorine; n is 0, 1 or 2, preferably 0 or 1; R2é independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy, C1-Cloxy, C1-C6-alkylamino, di-C1-C6alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyla, C2-C6haloalkynyla, C1-C6-alkylsulfonyl, arylsulfanyl, C1-C6-alkylsulfonyl, alkylsulfonyl, Cl arylsulfonyl, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, C3-C10-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, -C(=O)R21, -C(O)2, -C(O)(O) -C(=O)N(OR21)R21, C(=O)NR21N(R21)2, -C(=S)N(R21)2, -C(=NOR21)R21, -N(R21)2, -NR21C(=O)OR21, NR21C(=O)N(R21)2, -NR21C(=O -NR21C(=S)R21, -NR21C(=S)N(R21)2, NR21C(=NR21)R21, -OC(=O)R21, -OC(=O)N(R21)2, -NR21S(=O)2R21, -S(=O)2R21, S(=O)2N(R21)2 -O-C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl, Petition 870250043647, of 27 / 05 / 2025, p.31 / 149. 28 / 125 Ci-C6-(halo)alkyl-O-C3-Cio-carbocyclyl, -Ci-C6-(halo)alkyl- 3- to 10-membered heterocyclyl, -Ci-C6-(halo)alkyl-O-, 3- to 10-membered heterocyclyl, -C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-heteroaryloxy, C1-C6-(halo)alkyl-OR21, -C1-C6-(halo)alkyl-C(=O)R21, -C1-Ce-(halo)alkyl-C(=O)OR21, -C1-C6-(halo)alkyl-C(=O)N(R21)2, -C1-Ce-(halo)alkylaC(=O)N(OR21)R21, -C1-C6-(halo)alkyla-C(=O)NR21N(R21)2, -C1-Ce-(halo)alkylaC(=S)N(R21)2, -C1-C6-(halo)alkylaa-N(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)OR21, C1-C6-(halo)alkyl-NR21C(=O)N(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)R21, -C1-C6(halo)alkyl-NR21C(=S)R21, -C1-C6-(halo)alkyla-NR21C(=S)N(R21)2, -C1-C6(halo)alkyl-OC(=O)R21, -C1-C6-(halo)alkyl-OC(=O)N(R21)2, -C1-C6-(halo)alkylNR21S(=O)2R21, -C1-C6-(halo)alkyl-SR21, -C1-C6-(halo)alkyla-S(=O)R21, -C1-C6(halo)alkyla-S(=O)OR21, -C1-C6-(halo)alkyla-S(=O)2R21,-C1-C6-(halo)alkylS(=O)2OR21 and -C1-C6-(halo)alkyl-S(=O)2N(R21)2 wherein R21 is as described herein, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, wherein the acyclic radicals R2 and R21 may be substituted by one or more substituents R22 and the cyclic radicals R2 and R21 may be substituted by one or more substituents R22c, R22 and R22c being as described herein.

[089] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), R1 is a hydrogen atom.

[090] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), X is hydrogen.

[091] In some modalities, according to modalities (Ia), (Ib) and (Ic), X is fluorine.

[092] In some forms, according to forms (Ia), (Ib) and (Ic), X is chlorine. Petition 870250043647, dated 05 / 27 / 2025, p. 32 / 149 29 / 125

[093] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), R1 is a hydrogen atom and X is a chlorine atom.

[094] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), R1 is a hydrogen atom and X is a fluorine atom.

[095] In some modalities, according to modalities (Ia), (Ib) and (Ic), n is 1.

[096] In some modalities, according to modalities (Ia), (Ib) and (Ic), n is 1 in is 0.

[097] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), R2 is independently selected from the group consisting of halogen, cyano, C1-C6-alkyl (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl), C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino (e.g., methylamino), di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkylsulfonyl, Ca-Cw-carbocyclyl, aryl (e.g., phenyl), heteroaryl, -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-C1-Ce-(halo)alkyl-aryl, -C1-C6(halo)alkyl-C3-C10-carbocyclyl, -C1-C6-(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21 and -C1-C6-(halo)alkyl-C(=O)OR21 with R21 being as described herein, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl.The acyclic or cyclic radicals R2 and R21 can be substituted as described in this document, preferably substituted with halogen or C1-C6 (halo)alkyl.

[098] In some embodiments, according to embodiments (Ib) and (Ic), compounds are excluded in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is methyl or ethyl. Petition 870250043647, dated 05 / 27 / 2025, p. 33 / 149 30 / 125

[099] In some embodiments, according to embodiments (Ib) and (Ic), compounds are excluded in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[0100] In some embodiments, according to embodiments (Ib) and (Ic), compounds are excluded where Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[0101] In some embodiments, according to embodiments (Ib) and (Ic), compounds are excluded where Het is pyrazolyl or oxadiazolyl, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[0102] In some modalities, according to modalities (Ib) and (Ic), n is 1 or 2, and R2 independently selected from the group consisting of halogen, cyano, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkylsulfonyl, Ca-Cw-carbocyclyl, aryl, heteroaryl, -C(=O)R21, C(=O)OR21, -N(R21)2, -O-C1-Ce-(halo)alkyl-aryl, -C1-Ce-(halo)alkyl-C3-C10carbocyclyl, -C1-C6-(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6(halo)alkyl-aryl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21 and -C1-C6(halo)alkyl-C(=O)OR21 with R21 being as described herein and wherein the acyclic or cyclic radicals R2 and R21 may be substituted as described herein. Preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkylaryl, and the radicals R2 and R21 may be substituted by halogen or C1-C6(halo)alkyl.

[0103] In some embodiments (referred to in this document as embodiment Id), the compounds of the present invention are compounds of formula (I) Petition 870250043647, dated 05 / 27 / 2025, p. 34 / 149 31 / 125 in which R1 is selected from the group consisting of hydrogen, C1-C6-alkyl and C(=O)Ra, where Ra is a C1-C6-alkyl (e.g., methyl), preferably R1 is hydrogen; m is 0 or 1; Het is selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl and tetrazolyl; X is a hydrogen, fluorine, or chlorine atom, preferably fluorine; n is 0, 1, or 2; R2 is independently selected from the group consisting of halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6-alkylsulfonyl, C3-C10-carbocyclyl (preferably C3-C6carbocyclyl), aryl (e.g., phenyl), heteroaryl (preferably a 5- or 6-membered heteroaryl comprising one or two heteroatoms, e.g., thienyl, pyridinyl), -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-C1-C6-(halo)alkyl-aryl, -C1-C6(halo)alkyl-C3-C10-carbocyclyl, -C1-C6-(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21 and -C1-C6-(halo)alkyl-C(=O)OR21 with R21 being as described in this document; preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, and the Petition 870250043647, dated 05 / 27 / 2025, p. 35 / 149 32 / 125 acyclic or cyclic radicals R2 and R21 may be substituted as described in this document, preferably substituted with halogen or C1-C6-(halo)alkyl.

[0104] In some embodiments, according to the embodiment (Id), R2 is independently selected from the group consisting of fluorine, chlorine, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridinyl, -C(=O)H, methylcarbonyl, tert-butyloxycarbonyl, -CH2-cyclopropyl, -CH2-(N-morpholinyl), -CH2-phenyl (benzyl), -CH2-thienyl, -CH2-pyridinyl, methoxyethyl, -CH2-C(=O)OH, -CH2-C(=O)O-methyl and -CH2C(=O)O-ethyl, wherein the acyclic and cyclic R2 radicals may be substituted by halogen or C1-C6-(halo)alkyl. In particular, phenyl radicals can be replaced by halogens, for example, fluorine or chlorine.

[0105] In some embodiments, according to the embodiment (Id), compounds are excluded in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is methyl or ethyl.

[0106] In some embodiments, according to the embodiment (Id), compounds are excluded in which R1 is hydrogen, X is F, Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[0107] In some embodiments, according to the embodiment (Id), compounds are excluded where Het is pyrazolyl, m is 0, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[0108] In some embodiments, according to the embodiment (Id), compounds are excluded where Het is pyrazolyl or oxadiazolyl, n is 0 or 1, and R2 (if present) is C1-C6-alkyl.

[0109] In some modalities, according to the modality (Id), n is 1, 2, 3 or 4, preferably 1 or 2, and R2 is independently selected from the group consisting of halogen, cyano, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6. Petition 870250043647, dated 05 / 27 / 2025, page 36 / 149 33 / 125 alkenyl, C2-C6-alkynyl, C2-C6-haloalkenyl, C2-C6-haloalkynyl, C1-C6alkylsulfonyl, C3-Cio-carbocyclyl, aryl, heteroaryl, -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-Ci-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl, -C1-C6(halo)alkyl-3- to 10-membered heterocyclyl, -C1-C6-(halo)alkyl-aryl, -C1-C6(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21e -C1-C6-(halo)alkyl-C(=O)OR21 with R21 being as described in the present document and wherein the acyclic or cyclic radicals R2 and R21 may be substituted as recited in claim 1. Preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, and the radicals R2 and R21 may be substituted by halogen or C1-C6-(halo)alkyl.

[0110] In some embodiments, according to the embodiment (Id), n is 1, 2, 3 or 4, preferably 1 or 2, R2 is independently selected from the group consisting of fluorine, chlorine, cyano, propyl, isopropyl, butyl, isobutyl, trifluoromethyl, difluoromethyl, methoxy, allyl, cyclopropyl, cyclopentyl, phenyl, thienyl, pyridinyl, -C(=O)H, methylcarbonyl, tert-butyloxycarbonyl, -CH2-cyclopropyl, -CH2-(N-morpholinyl), -CH2-phenyl (benzyl), -CH2-thienyl, CH2-pyridinyl, methoxyethyl, -CH2-C(=O)OH, -CH2-C(=O)O-methyl and -CH2-C(=O)O-ethyl, wherein the acyclic and cyclic R2 radicals may be substituted by halogen or C1-C6-(halo)alkyl. In particular, phenyl radicals can be substituted by halogen, for example, fluorine or chlorine.

[0111] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), Het is selected from the group consisting of pyrazolyl, isothiazolyl and oxadiazolyl.

[0112] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), R2 is selected from the group consisting of C1-C6-haloalkyl, such as trifluoromethyl and difluoromethyl.

[0113] The present invention also relates to any compounds of formula (I) disclosed in Table 1. Petition 870250043647, dated 05 / 27 / 2025, p. 37 / 149 34 / 125

[0114] The present invention relates to compounds of formula (I) selected from the group consisting of ethyl 2-[4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyrazol-1-yl]acetate, 1-[5-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophen-2-yl]ethanone, 3-(4-thiophen-3-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(4-fluorophenyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[chloro(difluoro)methyl]-3-[4-(1-ethylpyrazol-4-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(4-methylthiophen-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-phenyl-1,3-thiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-thiophen-2-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-methylpyrrol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-methylpyrrol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-(1,3,5-trimethylpyrazol-4-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(1-propan-2-ylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-phenylthiophen-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,5-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbaldehyde, 3-[4-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol5-ol, 3-[4-(1-Ethylpyrazol-4-yl)-3-fluorophenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[5-(morpholin-4-ylmethyl)thiophen-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-Methoxythiophen-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-propan-2-yl-1,3-thiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(furan-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[2-fluoro-4-(1-methylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[chloro(difluoro)methyl]-3-[4-(1,2-oxazol-4-yl)phenyl]-4H-1,2-oxazol-5-ol, Petition 870250043647, de 27 / 05 / 2025, p. 38 / 149 35 / 125 3-[4-(1-benzylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(2-methoxyethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, [3-[4-(1-ethylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-yl]acetato, 3-[4-(1-propylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 2-[4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyrazol-1 yl]acetic acid, 3-[4-(5-methylfuran-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[chloro(difluoro)methyl]-3-[4-(1-methylpyrazol-4-yl)phenyl]-4H-1,2-oxazol-5-ol, 4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyrazole-1-carboxylate tert-butyl, 3-[4-(1,3-dimethylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-cyclopentylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-imidazol-1-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-phenylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[1-(thiophen-2-ylmethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-methyl-1,2-oxazol-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-ethyltriazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[2-fluoro-4-(1,2-oxazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, [3-[4-(1-ethylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-yl] 2-methoxyacetate, [3-[4-(1-ethylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-yl]acetato, 3-[4-(1-Ethylpyrazol-4-yl)-2-fluorophenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-chlorothiophen-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbonitrile, 3-[4-(1-methylpyrrol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-cyclopentyl-1,2,4-oxadiazol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5ol, Petition 870250043647, de 27 / 05 / 2025, p. 39 / 149 36 / 125 3-[4-[5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2oxazol-5-ol, 3-[4-[5-(2,4-difluorophenyl)-1,3,4-oxadiazol-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2oxazol-5-ol, 3-[4-[5-(difluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2oxazol-5-ol, 3-[4-(5-cyclopentyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol5-ol, 3-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2oxazol-5-ol, 3-[4-(5-tert-butyl-1,3,4-thiadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-tert-butylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-prop-2-enylimidazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]phenyl]-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-4H-1,2oxazol-5-ol, 3-[4-(1-pyridin-2-ylpyrazol-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbaldehyde, 4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbaldehyde, 5-methyl-3-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]thiophene-2-carbaldehyde, 3-[4-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, Petition 870250043647, de 27 / 05 / 2025, p. 40 / 149 37 / 125 3-[4-(5-tert-butyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5ol, 3-[4-(1,3-thiazol-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1,2-thiazol-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1,2-thiazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5ol, 3-[4-[1-(cyclopropylmethyl)pyrazol-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol and 3-[4-(1-cyclopropylpyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol.

[0115] The compounds of formula (I) according to the present invention can be used as fungicides (i.e., to control phytopathogenic fungi, in particular, fungi causing rust diseases, or Oomycetes in crop protection). PROCESSES FOR PREPARING FORMULA 1 COMPOUNDS

[0116] The compounds of formula (I) can be prepared according to the processes described in document WO2008 / 006561 and in document WO2019 / 122393.

[0117] The following table lists the abbreviations used in this paragraph and in Examples section, provided they are not explained in the body of the text. Abbreviation Meaning Ac Acetyl AIBN α,α'-azobisisobutyronitrile Boc tert-butyloxycarbonyl c-cyclo- Cl chemical ionization DCM Dichloromethane DIPEA N,N-diisopropylethylamine D MAP N,N-dimethylaminopyridine DMF N,N-dimethylformamide Petition 870250043647, dated 05 / 27 / 2025, p. 41 / 149 38 / 125 DMSO Dimethyl sulfoxide EDCI 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride eq. Equivalent ESI electrospray ionization h Hours HATU O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate HPLC High-performance liquid chromatography LC-MS Mass spectrometry and liquid chromatography MS Mass spectrometry: NMR Nuclear magnetic resonance spectroscopy: chemical shifts (δ) are given in ppm. OTf Trifluoromethylsulfonyl-PG Protecting group ppm parts per million Rf at reflux rt or rt room temperature T3P 1-propanephosphonic acid cyclic anhydride TEA Triethylamine TFA Trifluoroacetic acid THF Tetrahydrofuran

[0118] It is understood that, when in aqueous medium, compounds of formula (I') in which R1 is hydrogen and R2, X, m, ne Het are as defined above, may be present in a reversible equilibrium with the corresponding open form (i.e., compounds of formula (I'-I)). Petition 870250043647, dated 05 / 27 / 2025, p. 42 / 149 39 / 125 I' I Het I I (R2)n N(F)m I HO I'-I General synthetic routes for compounds of general formula I

[0119] The present invention also relates to processes for the preparation of the compounds of formula (I). Unless otherwise indicated, the radicals X, R1, R2, m, n, and Het have the meanings given above for the compounds of formula (I). These definitions apply not only to the final products of formula (I), but also to all intermediates.

[0120] The compounds of formula (I'), wherein R1 = H, can be prepared, according to process P1, by reacting diketones of formula (II) with hydroxylamine (or its hydrochloride salt) in the presence of a base, such as sodium hydroxide or sodium acetate in water and / or in a solvent, such as ethanol (as previously described in J. Org. Chem., 1995, 60, 3907-3909) or in the presence of an acid, such as acetic acid, optionally in a solvent such as ethanol (as described, for example, in the Journal of Heterocyclyc Chemistry, 2010, 47(6), 1310-1316). R2) XF n R2)n (II) (I') Process P1

[0121] The diketones of formula (II) can be prepared according to known procedures (see for example document WO2008006561), as shown in process P2 by treating ketones of formula (III) with a suitable base, preferably in a solvent (e.g., sodium ethoxide in ethanol). Petition 870250043647, dated 05 / 27 / 2025, p. 43 / 149 40 / 125 or sodium hydride in THF), followed by the addition of a fluoroacetyl electrophile, for example, ethyl trifluoroacetate. (5es)H iQMr2) pJUuQ^R2)n(F)m 0 0 (III)(Il) P2 Process

[0122] It is understood that the intermediates of formula (II) according to the invention, wherein X, R2, m, n, and Het are as defined above, may be present as the diketone (as represented in Processes P1 and P2) or as the ketoenol form or a mixture of both forms. Both forms or a mixture of both forms are suitable for carrying out process P2.

[0123] The compounds of formula (III) may be commercially available or may be prepared from readily available compounds according to known procedures.

[0124] The compounds of formula (I) can be prepared, according to process P3, by reacting compounds of formula (I'), where R1 = H, with an electrophile of formula (IV), where LG1 is a labile group such as, for example, chlorine, optionally in the presence of a suitable base, such as, for example, triethylamine, in a suitable solvent such as, for example, DCM or THF (see, for example, Journal Petition 870250043647, dated 05 / 27 / 2025, p. 44 / 149 41 / 125 Process P3

[0125] The compounds of formula (IV) may be commercially available or may be prepared from readily available compounds according to known procedures.

[0126] Alternatively, compounds of formula (I) can be prepared, according to process P4, from a compound of formula (V), where W1 is a labile group, such as bromine, by cross-coupling reaction with a compound of formula (VI), where M1 is a metal or metalloid (e.g. B(OH)2 or -ZnCl) in the presence of a base (such as cesium carbonate) and a catalyst (such as Tetrakis(triphenylphosphine)palladium (0)) in a solvent, such as dioxane and water. R1~oo^N(F)m XF (V) Process P4 (I)

[0127] Compounds of formula (V) can be prepared from readily available compounds in a manner analogous to processes P1 and P2.

[0128] The compounds of formula (VI) may be commercially available or may be prepared from readily available compounds according to known procedures. Alternatively, the compounds of formula (VI) may be generated in situ from the corresponding halo derivative by halogen-metal exchange prior to the cross-coupling reaction.

[0129] Alternatively, compounds of formula (I) can be prepared, according to process P5, from a compound of formula (VII), where M2 is a metal or metalloid (for example, -B(OH)2 or -ZnCl), by coupling reaction. Petition 870250043647, dated 05 / 27 / 2025, p. 45 / 149 42 / 125 crossed with a compound of formula (VIII), wherein W2 is a labile group, such as bromine, in the presence of a base (such as cesium carbonate) and a catalyst (such as Tetrakis(triphenylphosphine)palladium(0)) in a solvent, such as dioxane and water. (VII) XF R1~O M2 n F (I) R1-0 Process P5

[0130] The compounds of formula (VIII) may be commercially available or may be prepared from readily available compounds according to known procedures.

[0131] The compounds of formula (VII) can be prepared, according to process P6, from the compounds of formula (V), wherein W1 is a labile group, such as bromine, for example, by halogen metal exchange or by palladium-catalyzed borylation. Processes P6 and P5 can be combined into a single-vessel process. (V) XF R1—O W1 (VII) Process P6

[0132] According to the invention, processes P1 to P6 can be carried out, if appropriate, in the presence of a solvent and, if appropriate, in the presence of a base.

[0133] The solvents suitable for carrying out processes P1 to P6 according to the invention are the usual inert organic solvents. It is given Petition 870250043647, dated 05 / 27 / 2025, pp. 46 / 149 43 / 125 preference to the use of aliphatic, alkyl or aromatic hydrocarbons, optionally halogenated, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; Amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate; sulfoxides, such as dimethyl sulfoxide; or sulfones, such as sulfolan.

[0134] The appropriate bases for carrying out processes P1 to P6 according to the invention are the usual inorganic and organic bases for such reactions. Preference is given to the use of alkaline earth metals, alkali metal hydrides, alkali metal hydroxides or alkali metal alkoxides, such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, potassium tert-butoxide or other ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, alkali or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, 1,4-diazabicyclo[2,2,2]octane (DABCO), 1,5-diazabicyclo[4,3,0]non-5-ene (DBN) or 1,8-diazabicyclo[5,4,0]undec-7ene (DBU).

[0135] When carrying out processes P1 to P6, according to the invention, the reaction temperature can be varied independently within a relatively wide range. Generally, the processes according to the invention are carried out at temperatures between -20 °C and 160 °C. Petition 870250043647, dated 05 / 27 / 2025, page 47 / 149 44 / 125

[0136] Processes P1 to P6 according to the invention are generally carried out independently of atmospheric pressure. However, it is also possible to operate under high or low pressure.

[0137] Processing is carried out by usual methods. Generally, the reaction mixture is treated with water and the organic phase is separated and, after drying, concentrated under reduced pressure. If appropriate, the remaining residue can be released by usual methods, such as chromatography or recrystallization, of any impurities that may still be present.

[0138] The compounds according to the invention can be prepared according to the processes described above. However, it will be understood that, based on their general knowledge and available publications, those skilled in the art will be able to adapt these processes according to the specificities of each of the compounds according to the invention that they wish to synthesize.

[0139] Aspects of the present teaching can be better understood in the light of the following examples, which should not be interpreted as limiting the scope of the present teaching in any way. Compositions and formulations

[0140] The present invention also relates to a composition, in particular, a composition for controlling undesirable microorganisms, comprising one or more compounds of formula (I). The composition is preferably a fungicidal composition.

[0141] The composition typically comprises one or more compounds of formula (I) and one or more acceptable carriers, in particular one or more agriculturally acceptable carriers.

[0142] A carrier is a solid or liquid substance, natural or synthetic, organic or inorganic, that is generally inert. The carrier usually improves the application of compounds, for example, to plants, plant parts, or seeds. Petition 870250043647, dated 05 / 27 / 2025, pages 48 / 149 45 / 125 Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural rock flours such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, and synthetic rock flours such as finely divided silica, alumina, and silicates. Examples of solid carriers typically useful for the preparation of granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, and dolomite, synthetic granules of inorganic and organic flours, and granules of organic material such as paper, sawdust, coconut husks, corn cobs, and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof.Examples of suitable solvents include polar and non-polar organic chemical liquids, for example, from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may also be optionally substituted, etherified and / or esterified, such as butanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide), lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as sulfoxide of dimethyl).The vehicle may also be a liquefied gaseous diluent, that is, a liquid that is gaseous at standard temperature and under standard pressure, for example, aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide. The amount of vehicle typically ranges from 1 to 99.99%, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, and most preferably from 20 to 99% by weight of the composition. Petition 870250043647, dated 05 / 27 / 2025, pp. 49 / 149 46 / 125

[0143] The composition may also include one or more acceptable excipients that are common in the formulation of compositions (e.g., agrochemical compositions), such as one or more surfactants.

[0144] The surfactant may be an ionic (cationic or anionic) or non-ionic surfactant, such as ionic or non-ionic emulsifier(s), foam former(s), dispersant(s), wetting agent(s) and any mixtures thereof.Examples of suitable surfactants include, but are not limited to, polyacrylic acid salts, lignosulfonic acid salts, phenolsulfonic acid or naphthalene sulfonic acid salts, ethylene and / or propylene oxide polycondensates with fatty alcohols, fatty acids or fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example, alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), sulfosuccinic ester salts, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols and derivatives of compounds containing sulfates, sulfonates, phosphates (for example, alkyl sulfonates, alkyl sulfates, aryl sulfonates) and hydrolysates of protein, residual liquors of lignosulfite and methylcellulose.A surfactant is typically used when the compound of formula (I) and / or the vehicle is insoluble in water and the application is made with water. Then, the amount of surfactants typically ranges from 5 to 40% by weight of the composition.

[0145] Other examples of auxiliaries that are common in the formulation of agrochemical compositions include water repellents, desiccants, binders (adhesive, tackifying agent, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose), thickeners, stabilizers (e.g., cold stabilizers, preservatives, antioxidants, light stabilizers or other agents that improve Petition 870250043647, dated 05 / 27 / 2025, page 50 / 149 47 / 125 chemical and / or physical stability), paints or pigments (such as inorganic pigments, for example, iron oxide, titanium oxide and Prussian blue; organic dyes, for example, alizarin, azo and metal phthalocyanine dyes), antifoaming agents (for example, silicone antifoaming agent and magnesium stearate), preservatives (for example, dichlorophene and hemiformal benzyl alcohol), secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and finely divided silica), adhesives, gibberellins and processing aids, mineral and vegetable oils, perfumes, waxes, nutrients (including residual nutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts), protective colloids, thixotropic substances, penetrants, sequestering agents and complex formers.

[0146] The choice of auxiliaries is related to the intended application of the compound of formula (I) and / or to the physical properties. In addition, auxiliaries may be chosen to impart particular properties (technical, physical and / or biological properties) to the compositions or forms of use prepared from them. The choice of auxiliaries may allow the compositions to be customized for specific needs.

[0147] The composition may be in any usual form, such as solutions (e.g., aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, powders, dust, pastes, soluble powders, soluble granules, diffusion granules, suspoemulsion concentrates, natural or synthetic products impregnated with the compound of the invention, fertilizers, and also microencapsulations in polymeric substances. The compound of formula (I) may be present in a suspended, emulsified, or dissolved form.

[0148] The composition can be supplied to the end user as a ready-to-use formulation, i.e., the compositions can be applied directly to plants or seeds by a suitable device, such as a device of Petition 870250043647, dated 05 / 27 / 2025, page 51 / 149 48 / 125 spraying or dusting. Alternatively, the composition may be supplied to the end user in the form of concentrates which must be diluted, preferably with water, before use.

[0149] The composition can be prepared in conventional ways, for example, by mixing the compound of formula (I) with one or more suitable auxiliaries, as disclosed above.

[0150] The composition generally contains from 0.01 to 99% by weight, from 0.05 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight, more preferably from 1 to 80% by weight of the compound of formula (I).

[0151] The compound(s) and composition(s) comprising them may be mixed with other active ingredients such as fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, plant protectants or semiochemicals. This may allow for the broadening of the spectrum of activities or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in the Pesticide Manual, 17th Edition.

[0152] Examples of fungicides that can be mixed with the compound(s) of formula (I) and the composition of the invention are: 1) Inhibitors of ergosterol biosynthesis, for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) phenhexamide, (1.005) phenpropidine, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalyl sulfate, (1.012) propiconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1,019) pyrisoxazole, (1,020) spiroxamine, (1,021) tebuconazole, (1,022) tetraconazole, (1,023) triadimenol, (1,024) tridemorph, (1,025) triticonazole, (1,026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2- Petition 870250043647, dated 05 / 27 / 2025, page 52 / 149 49 / 125 (chloromethyl)-2-methyl-1 -(1 H-1,2,4-triazol-l -ylmethyl)cyclopentanol, (1.028) (2R)-2-(1chlorocyclopropyl)-4-[(1 R)-2,2-dichlorocyclopropyl]-1 -(1 H-1,2,4-l-triazol, -yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1 S)-2,2-dichlorocyclopropyl]-1 -(1 H-1,2,4-triazol-1 yl)butan-2-ol, (1.030) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 H-1,2,4triazol-1 -yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1 R)-2,2dicloclo-(11] H-1,2,4-triazol-1 -yl)butan-2-ol, (1.032) (2S)-2-(1 chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1 -(1 H-1,2,4-triazol-1 -yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)propan2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3yl)methanol, (1.035) (C)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4yl](pyridin-3-yl)methanol, (1036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol4-yl](pyridine-3-yl)methanol, (1,037) 1 -({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl1,3-dioxolan-2-yl}methyl)-1 H-1,2,4-triazole, (1,038) 1 -({(2S,4S)-2-[2-chloro-4-(4chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1,039) thiocyanate of 1 -{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazol-5-yl, (1,040) thiocyanate de1 -{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H1,2,4-triazol-5-yl, (1,041) thiocyanate of 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazol-5-yl, (1,042) 2-[(2R,4R,5R)-1 -(2,4dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1,043) 2-[(2R,4R,5S)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptane-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (1.044) 2-[(2R,4S,5R)-1 -(2,4-dichlorophenyl)-5-hydroxy2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3thiona, (1.046) 2-[(2S,4,4R)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]2,4-di-hydro-3H-1,2,4-triazole-3-thione, (1,047) 2-[(2S,4R,5S)-1 -(2,4-dichlorophenyl)-5hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3-thione, (1.048) 2[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3HPetição 870250043647, of 27 / 05 / 2025, p. 53 / 149. 50 / 125 1,2,4-triazol-3-thione, (1,049) 2-[(2S,4S,5S)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-di-hydro-3H-1,2,2,4-trial 2-[1 -(2,4-dichlorophenyl)-5hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1,051) 2-[2chloro-4-(2,4-1-phenyl-dichloro] H-1,2,4-triazol-1 -yl)propan-2-ol, (1,052) 2-[2-chloro4-(4-chlorophenoxy)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)butan-2-ol, (1,053) 2-[4-(4-chlorophenoxy)2-(trifluoromethyl)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)butan-2-ol, (1,054) 2-[4-(4-chlorophenoxy)-2(trifluoromethyl,-2,1-phenyl]-1 -yl)pentan-2-ol, (1,055) mefentrifluconazole, (1,056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-di-hydro-3H-1,2,30-triazol 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2yl]methyl}-2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1,058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1.059) 5-(4chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1 -{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N'-(2,5dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N'-(2,5-dimethyl-4-{[3(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N'-(2,5dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.067)068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-Nmethylimidoformamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N'-(2,5dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1,071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N-[32-Pethiumdoformamide). 870250043647, of 27 / 05 / 2025, p. 54 / 149. 51 / 125 (difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methyl-midoformamide (1.74). N'-[5-bromo-6-(2,3-di-hydro-1 H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-Nmethylimidoformamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-Nethyl-N-methylimidoformamide, (1.076) N'-{5-bromo-6-[(1 R)-1 -(3,5-difluorophenyl)ethoxy]-2methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1,077) N'-{5-bromo-6-[(1S)-1 -(3,5difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-methylimidoformamide, (1.078) N'-{5bromo-6-[(cis-4-isopropylcyclo-hexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-Nmethylimidoformamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclo-hexyl)oxy]-2methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N'-{5-bromo-6-[1 -(3,5difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.081) ipfentrifluconazole, (1.082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4triazol-1-yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 (1,2,4-triazol-1 -yl)propan-2-ol, (1.085) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, (1.086) 4-[[6-[rac-(2R)-2-(2,4difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3pyridyl]oxy]benzonitrile, (1.087) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1) hydroxy-1-phenylethyl)phenyl]-N-methylimidoformamide, (1.088) N'-{5-bromo-2-methyl-6-[(1propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.089) hexaconazole, (1.090) penconazole, (1.091) fenbuconazole (1.092) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]2-hydroxy-3-(1,2,4-triazol-1-yl)propanoato de methyl. 2) Respiratory chain inhibitors in complex I or II, for example (2.001) benzovindiflupir, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopiram, (2.006) flutolanil, (2.007) fluxapiroxad, (2.008) furomethpyr, (2.009) isofetamid, (2.010) isopirazam (antiepimeric enantiomer 1R,4S,9S), (2.011) isopirazam (antiepimeric enantiomer 1S,4R,9R), (2.012) isopirazam (antiepimeric racemate) Petition 870250043647, dated 05 / 27 / 2025, p. 55 / 149 52 / 125 RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1 RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (synepimeric enantiomer 1R,4SR,9SR), (2.015) isopirazam (2.015). (syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pidiflumethofen, (2.020) Pidiflumetofen, (2.021) sedaxano, (2,022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-di-hydro-1 H-inden-4-yl)-1 H-pyrazole-4-carboxamide, (2,023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-hydro-2,3-1 H-inden-4-yl]-1 H-pyrazol-4carboxamide, (2.024) 1,3-dimethyl-N-[(3C)-1,1,3-trimethyl-2,3-di-hydro-1 H-inden-4-yl]-1 Hpyrazol-4-carboxamide, (2.025) -methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2yl]-1 H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1 H-indene-benzamide, 2.027). 3-(difluoromethyl)-1 -methyl-N-(1, 1,3-trimethyl-2,3di-hydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2028) inpirfluxam, (2.029) 3(difluorometil)-1 -metil-N-[(3S)-1, 1,3-trimetil-2,3-di-hidro-1 H-inden-4-il]-1 H-pirazol-4carboxamida, (2.030) fluindapir, (2.031) 3-(difluorometil)-N-[(3R)-7-fluoro-1,1,3trimetil-2,3-di-hidro-1 H-inden-4-il]-1 -metil-1 H-pirazol-4-carboxamida, (2.032) 3(difluorometil)-N-[(3S)-7-fluoro-1,1,3-trimetil-2,3-di-hidro-1 H-inden-4-il]-1 -metil-1 Hpirazol-4-carboxamida, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluorometil)piridin-2il]oxi}fenil)etil]quinazolin-4-amina, (2.034) N-(2-ciclopentil-5-fluorobenzil)-Nciclopropil-3-(difluorometil)-5-fluoro-1 -metil-1 H-pirazol-4-carboxamida, (2.035) N-(2terc-butil-5-metilbenzil)-N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1 H-pirazol-4carboxamida, (2.036) N-(2-terc-butilbenzil)-N-ciclopropil-3-(difluorometil)-5-fluoro-1metil-1 H-pirazol-4-carboxamida, (2.037) N-(5-cloro-2-etilbenzil)-N-ciclopropil-3(difluorometil)-5-fluoro-1-metil-1 H-pirazol-4-carboxamida, (2.038) isoflucipram, (2.039) N-[(1 R,4S)-9-(dichloromethylene)-1,2,3,4-tetra-hydro-1,4-methanonaphthalene-5-yl]-3(difluoromethyl)-1 -methyl-1 H-pyrazole-4-carboxamide, (2,040) N-[(1 S,4R)-9(dichloromethylene)-1,2,3,4-tetra-hydro-1,4-methanonaphthalene-5-yl]-3-(difluoromethyl)-1 -methyl1 H-pyrazole-4-carboxamide, (2,041) N-[1 -(2,4-dichlorophenyl)-1-pethioxy-pro-panethio-3] 870250043647, of 27 / 05 / 2025, p. 56 / 149. 53 / 125 (difluorometil)-1-metil-1 H-pirazol-4-carboxamida, (2.042) N-[2-cloro-6(trifluorometil)benzil]-N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1 H-pirazol-4carboxamida, (2.043) N-[3-cloro-2-fluoro-6-(trifluorometil)benzil]-N-ciclopropil-3(difluorometil)-5-fluoro-1-metil-1 H-pirazol-4-carboxamida, (2.044) N-[5-cloro-2(trifluorometil)benzil]-N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1 H-pirazol-4carboxamida, (2.045) N-ciclopropil-3-(difluorometil)-5-fluoro-1 -metil-N-[5-metil-2(trifluorometil)benzil]-1 H-pirazol-4-carboxamida, (2.046) N-ciclopropil-3(difluorometil)-5-fluoro-N-(2-fluoro-6-isopropilbenzil)-1-metil-1H-pirazol-4carboxamida, (2.047) N-ciclopropil-3-(difluorometil)-5-fluoro-N-(2-isopropil-5metilbenzil)-1 -metil-1 H-pirazol-4-carboxamida, (2.048) N-ciclopropil-3-(difluorometil)5-fluoro-N-(2-isopropilbenzil)-1 -metil-1 H-pirazol-4-carbothioamida, (2.049) Nciclopropil-3-(difluorometil)-5-fluoro-N-(2-isopropilbenzil)-1-metil-1H-pirazol-4carboxamida, (2.050) N-ciclopropil-3-(difluorometil)-5-fluoro-N-(5-fluoro-2isopropilbenzil)-1-metil-1 H-pirazol-4-carboxamida, (2.051) N-ciclopropil-3(difluorometil)-N-(2-etil-4,5-dimetilbenzil)-5-fluoro-1-metil-1 H-pirazol-4-carboxamida, (2.052) N-ciclopropil-3-(difluorometil)-N-(2-etil-5-fluorobenzil)-5-fluoro-1 -metil-1 Hpirazol-4-carboxamida, (2.053) N-ciclopropil-3-(difluorometil)-N-(2-etil-5-metilbenzil)5-fluoro-1-metil-1 H-pirazol-4-carboxamida, (2.054) N-ciclopropil-N-(2-ciclopropil-5fluorobenzil)-3-(difluorometil)-5-fluoro-1 -metil-1 H-pirazol-4-carboxamida, (2.055) Nciclopropil-N-(2-ciclopropil-5-metilbenzil)-3-(difluorometil)-5-fluoro-1-metil-1 H-pirazol4-carboxamida, (2.056) N-ciclopropil-N-(2-ciclopropilbenzil)-3-(difluorometil)-5-fluoro1-metil-1H-pirazol-4-carboxamida, (2.057) pirapropoína, (2.058) N-[rac-(1S,2S)-2(2,4-diclorofenil)ciclobutil]-2-(trifluorometil)nicotinamida, (2.059) N-[(1S,2S)-2-(2,4diclorofenil)ciclobutil]-2-(trifluorometil)nicotinamida. 3) Respiratory chain inhibitors in complex III, for example (3.001) ametoctradine, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumetoxystrobin, (3.005) coumoxystrobin, (3.006) ciazofamide, (3.007) dimoxystrobin, (3.008) Petition 870250043647, dated 05 / 27 / 2025, page 57 / 149 54 / 125 enoxastrobin, (3,009) famoxadone, (3,010) fenamidone, (3,011) fluphenoxystrobin, (3,012) fluoxastrobin, (3,013) cresoxim-methyl, (3,014) metominostrobin, (3,015) orisastrobin, (3,016) picoxystrobin, (3,017) pyraclostrobin, (3,018) pyrametostrobin, (3,019) pyroxystrobin, (3,020) trifloxystrobin, (3,021) (2E)-2-{2[({[(1 E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2(methoxy-imino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3yl]oxy}-2-(methoxy-imino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamide, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1 H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) Methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2methylbenzyl}carbamate, (3.030) methyltetraprole, (3.031) florylpicoxamide. 4) Inhibitors of mitosis and cell division, for example (4.001) carbendazim, (4.002) dietofencarb, (4.003) etaboxam, (4.004) fluopicolida, (4.005) pencicuron, (4.006) thiabendazol, (4.007) thiophanate-methyla, (4.008) zoxamida, (4.009) pyridachlomethyla, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.013) 4(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1 H-pyrazol-5amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1 H-pyrazol-5. Petition 870250043647, 05 / 27 / 2025, pág. 58 / 149 55 / 125 amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1 H-pyrazole-5amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,025) N-(4chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.026) fluopimomida. 5) Compounds capable of having a multisite action, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017) copper oxine, (5.018) propineb, (5.019) sulfur and sulfur preparations, including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazol-3-carbonitrile. 6) Compounds capable of inducing a host defense, for example (6.001) acibenzolar-S-methyl, (6.002) isothianyl, (6.003) probenazole, (6.004) thiadinyl. 7) Inhibitors of the biosynthesis of amino acids and / or proteins, for example (7,001) cyprodinil, (7,002) kasugamycin, (7,003) kasugamycin hydrochloride, (7,004) oxytetracycline, (7,005) pyrimethanil, (7,006) 3- (5-fluoro-3,3,4,4-tetramethyl-3,4dihydroisoquinoline-1-yl) quinoline. 8) Inhibitors of ATP production, for example (8.001) silthiofam. 9) Cell wall synthesis inhibitors, e.g. (9,001) bentiavalicarb, (9,002) dimetomorph, (9,003) flumorph, (9,004) iprovalicarb, (9,005) mandipropamide, (9,006) pyrimorph, (9,007) valifenalate, (9,008) (2E)-3-(4-tertbutylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tertbutylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one. Petition 870250043647, dated 05 / 27 / 2025, page 59 / 149 56 / 125 10) Lipid and membrane synthesis inhibitors, for example, (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl. 11) Inhibitors of melanin biosynthesis, for example, (11.001) tricycloazole, (11.002) tolprocarb. 12) Nucleic acid synthesis inhibitors, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (Chiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam). 13) Signal transduction inhibitors, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxifene, (13.006) vinclozoline. 14) Compounds capable of acting as an uncoupler, for example (14.001) fluazinam, (14.002) meptilidinocape. 15) Other fungicides selected from the group consisting of (15.001) abscisic acid, (15.002) bentiazole, (15.003) betoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionate, (15.007) cufraneb, (15.008) ciflufenamide, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl-aluminum, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyl dithiocarbamate, (15.020) isopropyl nitrothalamic acid, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfenthiamine, (15.024) pentachlorophenol and its salts, (15.025) phosphorous acid and its salts, (15.026) propamocarb fosetylate, (15.027) pyriophenone (clazafenone), (15.028) tebufloquine, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1 -(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-di-hydro-1,2-oxazol-3-yl]-1,3thiazol-2-yl}piperidin-1 -yl)-2-[5-methyl-3-nanopyl,)ano-trifluoromethyl (15,032) 1 (4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-di-hydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1yl)-2-[5-methyl-3-)(zoethano1-trifluoromethyl) (15,033) 2-(6-benzylpyridine-2yl)quinazoline, (15,034) dipimethitrone, (15,035) 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]-. Petition 870250043647, dated 05 / 27 / 2025, p. 60 / 149 57 / 125 -[4-(4-{5-[2-(prop-2-in-1 -yloxy)phenyl]-4,5-di-hydro-1,2-oxazol-3-yl}-1,3-thiazol-2yl)piperidin-1 -yl]ethanone, (15,036) 2-oromethyl()pira-diflu-3,5- -yl]-1 -[4-(4-{5-[2chloro-6-(prop-2-in-1 -yloxy)phenyl]-4,5-di-hydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1yl]luoroethanone, (15-methyl-3-37 H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-fluoro-6(prop-2-in-1 -yloxy)phenyl]-4,5-di-hydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-03,8 (yl]ethanone 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methylpyridine-2-yl]quinazoline, (15,039) 2-{(5R)-3-[2-(1-{[[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidine-4-yl)-1,3thiazol-4-yl]-4,5-di-hydro-1,2-oxazol-5-yl}-3-chlorophenyl methanosulfonate, (15,040) 2-{(5S)3-[2-(1 gold methyl -{pyra-[diflu-3,5- -yl]acetyl}piperidine-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanosulfonate, (15,041) ipflufenoquine, (15,042) 2{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15,043) fluoxapiproline, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1,3thiazol-4-yl]-4,5-di-hidro-1,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-phenylphenol e seus sais, (15.046) 3-(4,4,5-trifluoro-3,3-dimetil-3,4-di-hidroisoquinolin-1-yl)quinolina, (15.047) quinofumelin, (15.048) 4-amino-5-fluoropirimidin-2-ol (tautomeric form: 4amino-5-fluoropirimidin-2(1H)-ona), (15.049) ácido 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4-thiadiazol-2-thiol, (15.051) 5-chloro-N'phenyl-N'-(prop-2-in-1 -yl)thiophene-2-sulfono-hydrazide, (15.052) 5-fluoro-2-[(4fluorobenzyl)oxi]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxi]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-di-hydro-1,4-benzoxazepine, (15.055) but-3-in-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5yl)(phenyl)methylene]amino}oxi)methyl]pyridin-2-yl}carbamate, (15.056) (2Z)-3-amino-2cyano-3-ethyl phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) 3,4,5-trihydroxybenzoate of propylene glycol, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methyleno]amino}oxi)methyl]pyridin-2yl}carbamate of tert-butyl, (15.062) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]3,4-di-hydropyrimidin-2(1H)-one, (15.063) aminopyrifen, (15.064) (N'-[2-chloro-4-(2Petição 870250043647, de 27 / 05 / 2025, p. 61 / 149. 58 / 125 fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamida), (15.065) (N'-(2-chloro-5-methyl4-phenoxy-phenyl)-N-ethyl-N-methylimidoformamida), (15.066) (2-{2-[(7,8-difluoro-2metilquinolin-3-yl)oxi]-6-fluorofenyl}propan-2-ol), (15.067) (5-bromo-1 -(5,6dimetilpiridin-3-yl)-3,3-dimetil-3,4-di-hidroisoquinolina), (15.068) (3-(4,4-difluoro-5,5dimetil-4,5-di-hidrotieno[2,3-c]piridin-7-yl)quinolina), (15.069) (1 -(4,5-dimethyl-1 Hbenzimidazol-1 -yl)-4,4-difluoro-3,3-dimetil-3,4-di-hidroisoquinolina), (15.070) 8-fluoro3-(5-fluoro-3,3-dimetil-3,4-di-hidroisoquinolin-1-yl)quinolona, ​​(15.071) 8-fluoro-3-(5fluoro-3,3,4,4-tetrametil-3,4-di-hidroisoquinolin-1 -yl)quinolona, ​​(15.072) 3-(4,4-difluoro3,3-dimetil-3,4-di-hidroisoquinolin-1 -yl)-8-fluoroquinolina, (15.073) (N-methyl-N-phenyl-4[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamida), (15.074) {4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl}carbamate demethyl, (15.075) (N-{4-[5-(trifluorometil)-1,2,4oxadiazol-3-il]benzil}ciclopropanocarboxamida), (15.076) N-metil-4-(5-(trifluorometil)1,2,4-oxadiazol-3-il]benzamida, (15.077) N-[(E)-metóxi-iminometil]-4-[5(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.078) N-[(Z)-metóxi-iminometil]-4[5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.079) N-[4-[5-(trifluorometil)1,2,4-oxadiazol-3-il]fenil]ciclopropanecarboxamida, (15.080) N-(2-fluorofenil)-4-[5(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.081) 2,2-difluoro-N-metil-2-[4-[5(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]acetamida, (15.082) N-alil-N-[[4-[5(trifluorometil)-1,2,4-oxadiazol-3-il)fenil]metil]acetamida, (15.083) N-[(E)-N-metóxi-Cmetil-carbonimidoil]-4-(5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.084) N[(Z)-N-metóxi-C-metil-carbonimidoil]-4-[5-(trifluorometil)-1,2,4-oxadiazol-3il]benzamida, (15.085) N-alil-N-[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3il]fenil]metil]propanamida, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoropropanamide, (15.090) 1-methoxy-1-methyl-3-[[4Petição 870250043647, de 27 / 05 / 2025, p. 62 / 149. 59 / 125 [5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091) 1,1-diethyl-3-[[4-[5 (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.093) N-methoxy-N-[[4-[5 (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094) 1methoxy-3-methyl-1 -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) Nmethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl}1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propanamide, (15.098) 1 -methoxy-3-methyl1 -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 1,3-dimethoxy-1 [[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.100) 3-ethyl-1-methoxy-1 [[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101) 1 -[[4-[5(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]piperidin-2-ona, (15.102) 4,4-dimetil-2[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]isooxazolidin-3-ona, (15.103) 5,5dimetil-2-[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]isoxazolidin-3-ona, (15.104) 3,3-dimetil-1 -[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]piperidin-2ona, (15.105) 1 -[[3-fluoro-4-(5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]azepan-2ona, (15.106) 4,4-dimetil-2-[[4-(5-(trifluorometil)-1,2,4-oxadiazol-3il]fenil]metil]isoxazolidin-3-ona, (15.107) 5,5-dimetil-2-[[4-[5-(trifluorometil)-1,2,4oxadiazol-3-il]fenil]metil]isoxazolidin-3-ona, (15.108) etil 1-{4-[5-(trifluorometil)-1,2,4oxadiazol-3-il]benzil}-1 H-pirazol-4-carboxilate, (15.109) N,N-dimetil-1-{4-[5(trifluorometil)-1,2,4-oxadiazol-3-il]benzil}-1 H-1,2,4-triazol-3-amina, (15.110) N-{2,3difluoro-4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzil}butanamida, (15.111) N-(1methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15,112) N-(2,4difluorophenyl)-4-[5-(trifluoromethyl)-1,3)bezolza.4-dia1-oxa 1 -(5,6dimethylpyridine-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-di-hydroisoquinoline, (15,114) 1 -(6(difluoromethyl)-5-methyl-pyridine-3-yl)-4,4,3,3-hydrodifluorodimethyl-3,3 Petition 870250043647, dated 05 / 27 / 2025, p. 63 / 149 60 / 125 (15.115) 1 -(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-di-hydroisoquinoline, (15.116) 1 -(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3dimethyl-3,4-di-hydroisoquinoline, (15.117) 4-[5-(trifluoromethyl)1,2,4-oxadiazol-3-yl]phenyl dimethylcarbamate, (15.118) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yl]phenyl}propanamide, (15.119) methanesulfonate 3-[2-(1-{[5-methyl-3-(trifluoromethyl)1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-di-hidro-2,4-benzodioxepin-6-yl, (15,120) 9-fluoro-3-[2-(1 -{[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)1,3-thiazol-4-yl]-1,5-di-hidro-2,4-benzodioxepin-6-yl methanesulfonate, (15,121) 3-[2-(1{[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-di-hidro2,4-benzodioxepin-6-yl methanesulfonate, (15.122) 3-[2-(1-{[3,5bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.123) 1 -(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15,124) 8-fluoro-N-(4,4,4-trifluoro-2methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide, (15,125) 8-fluoro-N-[(2S)-4,4,4trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15,126) N-(2,4-dimethyl-1phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide and (15,127) N-[(2S)-2,4-dimethyl-1phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide.

[0153] All named mixing partners of classes (1) to (15), as described in the present document above, may be present in the form of the free compound and / or, if their functional groups permit, an agriculturally acceptable salt thereof.

[0154] The compounds of formula (I) and compositions comprising them may be combined with one or more biological control agents.

[0155] Examples of biological control agents that can be combined with the compounds of formula (I) and compositions comprising them are: (A) Antibacterial agents selected from the group of: Petition 870250043647, dated 05 / 27 / 2025, p. 64 / 149 61 / 125 (A1) bacteria, such as (A1.1) Bacillus subtilis, in particular, strain QST713 / AQ713 (available as SERENADE OPTI or SERENADE ASO available from Bayer CropScience LP, USA, having Accession Number NRRL B21661 and described in US Patent No. 6,060,051); (A1.2) Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ available from Certis, USA, having Accession Number FERM BP-8234 and disclosed in US Patent No. 7,094,592); (A1.3) Bacillus pumilus, in particular strain BU F-33 (having Accession Number NRRL 50185); (A1.4) Bacillus subtilis var. amyloliquefaciens FZB24 (available as Taegro® from Novozymes, USA); (A1.5) a Paenibacillus sp. strain having NRRL accession number B-50972 or NRRL accession number B-67129 and described in International Patent Publication no. WO 2016 / 154297; and (A2) fungi, such as (A2.1) Aureobasidium pullulans, in particular blastospores of strain DSM14940; (A2.2) blastospores of strain Aureobasidium pullulans DSM 14941; (A2.3) Aureobasidium pullulans, in particular blastospore mixtures of strains DSM14940 and DSM14941; (B) Fungicides selected from the group of: (B1) bacteria, for example (B1.1) Bacillus subtilis, in particular the QST713 / AQ713 strain (available as SERENADE OPTI or SERENADE ASO available from Bayer CropScience LP, US, having NRRL Accession No. B21661 and described in US Patent No. 6,060,051); (B1.2) Bacillus pumilus, in particular the QST2808 strain (available as SONATA® available from Bayer CropScience LP, US, having NRRL Accession No. B-30087 and described in US Patent No. 6,245,551); (B1.3) Bacillus pumilus, in particular the GB34 strain (available as Yield Shield® available from Bayer AG, DE); (B1.4) Bacillus pumilus, in particular strain BU F-33 (accession number NRRL 50185); (B1.5) Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ from Certis, US, accession number FERM BP-8234 and disclosed in US Patent No. 7,094,592); (B1.6) Bacillus Petition 870250043647, dated 05 / 27 / 2025, p. 65 / 149 62 / 125 subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277); (B1.7) Bacillus amyloliquefaciens strain MBI 600 (available as SUBTILEX from BASF SE); (B1.8) Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, DE); (B1.9) Bacillus subtilis var. strain FZB24 amyloliquefaciens (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina with the fungicide TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5); (B1.10) Bacillus mycoides, isolate J (available as BmJ TGAI or WG available from Certis USA); (B1.11) Bacillus licheniformis, in particular strain SB3086 (available as EcoGuard™ Biofungicide and Green Releaf available from Novozymes);having accession number NRRL B-50972 or accession number NRRL B-67129 and described in international patent publication no. WO 2016 / 154297.

[0156] In some embodiments, the biological control agent is a strain of Bacillus subtilis or Bacillus amyloliquefaciens that produces a fengicin- or plipastatin-like compound, an iturin-like compound, and / or a surfactin-like compound. For detailed information, see the following review article: Ongena, M., et al., “Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol,” Trends in Microbiology, Vol 16, No. 3, March 2008, pp. 115-125. Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (available as SERENADE OPTI or SERENADE ASO available from Bayer CropScience LP, USA, having Accession No. NRRL B21661e described in US Patent No.6,060,051), strain of Bacillus amyloliquefaciens D747 (available as Double Nickel™ from Certis, US, accession number FERM BP-8234 and disclosed in US Patent No. 7,094,592); Bacillus subtilis MBI600 (available as SUBTILEX® from Becker Underwood, USA, EPA Reg. No. 71840-8);. Petition 870250043647, dated 05 / 27 / 2025, p. 66 / 149 63 / 125 Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277); Bacillus amyloliquefaciens, in particular strain FZB42 (available as RHIZOVITAL® from ABiTEP, Germany); and Bacillus subtilis var. (B1) fungi, for example: (B2.1) amyloliquefaciens FZB24 (available from Novozymes Biologicals Inc., Salem, Virginia or Syngenta Crop Protection, LLC, Greensboro, North Carolina as the fungicide TAEGRO® or TAEGRO® ECO (EPA registration number 70127-5); and (B2) fungi, for example: (B2.1) Coniothyrium minitans, in particular strain CON / M / 91-8 (DSM accession number 9660; for example, Contans® available from Bayer); (B2.2) Metschnikowia fructicola, in particular strain NRRL Y-30752 (for example, Shemer®); (B2.3) Microsphaeropsis ochracea (for example, Microx® available from Prophyta);, including Trichoderma atroviride, strain SC1 described in international patent application no. PCT / IT2008 / 000196); (B2.6) strain KRL-AG2 of Trichoderma harzianum rifai (also known as strain T-22, / ATCC 208479, for example, PLANTSHIELD T-22G, Rootshield®, and TurfShield available from BioWorks, USA); (B2.14) Gliocladium roseum, strain 321U available from WF Stoneman Company LLC; (B2.35) Talaromyces flavus, strain V117b; (B2.36) Trichoderma asperellum, strain ICC 012 available from Isagro; (B2.37) Trichoderma asperellum, strain SKT-1 (for example, ECO-HOPE® available from Kumiai Chemical Industry); (B2.38) Trichoderma atroviride, strain CNCM I-1237 (e.g. Esquive® WP available from Agrauxine, FR); (B2.39) Trichoderma atroviride, strain no. V08 / 002387; (B2.40) Trichoderma atroviride, strain NMI no. V08 / 002388; (B2.41) Trichoderma atroviride, strain NMI no. V08 / 002389; (B2.42) Trichoderma atroviride, strain NMI no. V08 / 002390; (B2.43) Trichoderma atroviride, strain LC52 (e.g. Tenet by Agrimm Technologies Limited); (B2.44) Trichoderma atroviride, strain ATCC 20476 (IMI 206040); (B2.45) Trichoderma atroviride, strain T11 (IMI352941 / CECT20498); (B2.46). Petition 870250043647, dated 05 / 27 / 2025, page 67 / 149 64 / 125 Trichoderma harmatum; (B2. 47) Trichoderma harzianum; (B2. 48) Trichoderma harzianum rifai T39 (e.g., Trichodex® available near Makhteshim, USA); (B2. 49) Trichoderma harzianum, in particular, strain KD (e.g., Trichoplus available from Biological Control Products, SA (acquired by Becker Underwood)); (B2. 50) Trichoderma harzianum, strain ITEM 908 (e.g., Trianum-P available near Koppert); (B2. 51) Trichoderma harzianum, strain TH35 (e.g., Root-Pro by Mycontrol); (B2. 52) Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g., SoilGard 12G by Certis, USA); (B2. 53) Trichoderma viride, strain TV1 (e.g. Trianum-P by Koppert); (B2. 54) Ampelomyces quisqualis, in particular strain AQ 10 (e.g. AQ 10® by IntrachemBio Italy); (B2. 56) Aureobasidium pullulans, in particular, blastospores of strain DSM14940; (B2. 57) Aureobasidium pullulans, in particular, blastospores of strain DSM 14941; (B2.58) Aureobasidium pullulans, in particular, mixtures of blastospores of strains DSM14940 and DSM 14941 (e.g., Botector® by bioferm, CH); (B2.64) strain H39 de Cladosporium cladosporioides, (por Stichting Dienst Agricultural Research); (B2.69) Gliocladium catenulatum (Synonym: Clonostachys rosea f. catenulate) strain J1446 (for example, Prestop ® by AgBio Inc. and also for example Primastop® by Kemira Agro Oy); (B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia of strain KV01 (e.g., Vertalec® by Koppert / Arysta); (B2.71) Penicillium vermiculatum; (B2.72) Anomalous Pichia, strain WRL-076 (NRRL Y-30842); (B2.75) Trichoderma atroviride , strain SKT-1 (FERM P-16510); (B2.76) Trichoderma atroviride , strain SKT-2 (FERM P16511); (B2.77) Trichoderma atroviride , strain SKT-3 (FERM P-17021); (B2.78) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, for example BioDerma by AGROBIOSOL DE MEXICO, SA DE CV); (B2.79) Trichoderma harzianum, strain DB 103 (e.g. T-Gro 7456 by Dagutat Biolab); (B2. 80) Trichoderma polysporum, strain IMI 206039 (e.g. Binab TF WP by. Petition 870250043647, dated 05 / 27 / 2025, p. 68 / 149 65 / 125 BINAB Bio-Innovation AB, Sweden); (B2. 81) Trichoderma stromaticum (e.g. Tricovab by Ceplac, Brazil); (B2. 83) Ulocladium oudemansii, in particular strain HRU3 (e.g. Botry-Zen® by Botry-Zen Ltd, NZ); (B2. 84) Verticillium alboatrum (formerly V. dahliae), strain WCS850 (CBS 276.92; e.g. Dutch Trig by Tree Care Innovations); (B2. 86) Verticillium chlamydosporium; (B2. 87) mixtures of strain ICC 012 of Trichoderma asperellum and strain ICC 080 of Trichoderma gamsii (product known as e.g. BIO-TAMtm available from Bayer CropScience LP, USA).

[0157] Other examples of biological control agents that can be combined with the compounds of formula (I) and compositions comprising them are: Selected bacteria available from the group consisting of Bacillus cereus, in particular strain CNCM I-1562 of B. cereus and Bacillus firmus, strain I-1582 (accession number CNCM I-1582), Bacillus subtilis strain OST 30002 (accession number NRRL B-50421), Bacillus thuringiensis, in particular, B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (accession number ATCC 1276), B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), B. thuringiensis subsp. kurstaki strain HD-1, strain NB 176 of B. thuringiensis subsp. tenebrionis (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (ATCC accession number SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31013, NRRL B-50550), and Streptomyces galbus strain AQ 6047 (NRRL accession number 30232); Selected fungi and yeasts from the group consisting of Beauveria bassiana, in particular strain ATCC 74040, Lecanicillium spp., in particular strain HRO LEC 12, Metarhizium anisopliae, in particular strain F52 (DSM3884 or ATCC 90448), Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particular the Petition 870250043647, dated 05 / 27 / 2025, pp. 69 / 149 66 / 125 strain IFPC 200613, or strain Apopka 97 (ATCC Accession No. 20874), and Paecilomyces lilacinus, in particular, strain 251 of P. lilacinus (AGAL 89 / 030550); Selected viruses from the group consisting of Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beetroot caterpillar) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, and Spodoptera littoralis (African armyworm) NPV. Bacteria and fungi that can be added as "inoculants" to plants, plant parts, or plant organs, and which, due to their particular properties, promote plant growth and health. Examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., and Streptomyces spp. plant extracts and products formed by microorganisms including proteins and secondary metabolites that can be used as biological control agents, such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, ArmourZen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum / Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, Requiem™ Insecticide, rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract, in particular rapeseed Powdered or mustard powder. Petition 870250043647, dated 05 / 27 / 2025, page 70 / 149 67 / 125

[0158] Examples of insecticides, acaricides and nematicides, respectively, that can be mixed with the compounds of formula (I) and compositions comprising them are: (1) Acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, for example, alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, etiofencarb, fenobucarb, formetanate, furatiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimetacarb, XMC and xylylcarb;or organophosphates, for example, acephate, azamethifos, azinphos-ethyl, azinphos-methyl, cadusafos, chloridexifos, chlorfenvinfos, chlormefos, chlorpyrifos-methyl, coumafos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotofos, dimethoate, dimethylvinfos, disulfoton, EPN, ethion, etoprofos, famphur, fenamifos, fenitrothion, fenthion, fostiazate, heptenofos, imiciafos, isofenfos, isopropyl O(methoxyaminothiophosphoryl) salicylate, isoxation, malathion, mecarbam, methamidofos, metidation, mevinfos, monocrotofos, naled, ometoate, oxidemeton-methyl, parathion-methyl, fentoate, phorate, phosalone, phosmet, phosfamidone, foxim, pirimiphos-methyl, profenofos, propetamphos, protiofos, pyraclophos, pyridafenthion, quinalfos, sulfotep, tebupirimphos, temefos, terbufos, tetrachlorvinphos, thiometon, triazofos, trichlorfon and vamidothion. (2) GABA-controlled chloride channel blockers, such as cyclodiene-organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for example etiprole and fipronil. (3) Sodium channel modulators, such as, for example, pyrethroids, e.g., acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, pentenyl s-cycloisomer bioallethrin, bioresmethrin, cycloprothrin, cyfluthrin, beta-cypermethrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, Petition 870250043647, dated 05 / 27 / 2025, page 71 / 149 68 / 125 cifenotrin [(1R) [(EZ) - (1R) -isδmero], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, monfluorothrin, permethrin, prethrin-phenothrin] , pyrethrins (pyrethrum), resmethrin, silafluophen, tefluthrin, tetramethrin, tetramethrin [(1R) -isomer)], tralomethrin and transfluthrin or DDT or methoxychlor. (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as, for example, neonicotinoids, for example, acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupiradifurone. (5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR), such as, for example, spinosyns, for example, spinetoram and spinosad. (6) Allosteric modulators of glutamate-gated chloride channels (GluCl), such as, for example, avermectins / milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin. (7) Mimics of juvenile hormone, such as, for example, juvenile hormone analogues, for example, hydroprene, quinoprene and methoprene or fenoxycarb or pyriproxyfen. (8) Various non-specific inhibitors (multiple sites), such as, for example, alkyl halides, for example, methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic or methyl isocyanate generators, for example, diazomet and metame. (9) Modulators of chordotonal organs, such as, for example, pimetrozine or flonicamide. (10) Mite growth inhibitors, such as clofentezine, hexthiazine and diflovidazine or ethoxazole. (11) Microbial disruptors of the insect intestinal membrane, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus Petition 870250043647, dated 05 / 27 / 2025, page 72 / 149 69 / 125 thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and Bt plant proteins: CrylAb, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1. (12) Mitochondrial ATP synthase inhibitors, such as ATP disruptors, such as, for example, diafenthiuron or organotin compounds, for example, azocyclotine, cyhexatine and fenbutatine oxide or propargite or tetradiphone. (13) Uncouplers of oxidative phosphorylation by disrupting the proton gradient, such as chlorfenapyr, DNOC and sulfluramide. (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, tiocilam, and thiosultap-sodium. (15) Type 0 chitin biosynthesis inhibitors, such as bistriflurone, chlorfluazurone, diflubenzurone, flucicloxurone, flufenoxurone, hexaflumurone, lufenurone, novalurone, noviflumurone, teflubenzurone and triflumurone. (16) Inhibitors of chitin biosynthesis, type 1, for example, buprofezin. (17) Molt disruptor (in particular for diptera, i.e., diptera), such as cyromazine. (18) Ecdysone receptor agonists, such as, for example, cromofenozide, halofenozide, methoxyfenozide and tebufenozide. (19) Octopamine receptor agonists, such as, for example, amitraz. (20) Inhibitors of mitochondrial complex III electron transport, such as hydramethylone or acequinoline or fluacripyrim. (21) Mitochondrial inhibitors of electron transport of complex I, such as, for example, those of the METI acaricide group, for example, phenazaquin, fenpyroximate, pirimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris). (22) Voltage-dependent sodium channel blockers, such as indoxacarb or metaflumizone. Petition 870250043647, dated 05 / 27 / 2025, page 73 / 149 70 / 125 (23) Acetyl CoA carboxylase inhibitors, such as, for example, tetronic and tetramic acid derivatives, for example, spirodiclofen, spiromesifene and spirotetramat. (24) Mitochondrial inhibitors of complex IV electron transport, such as, for example, phosphines, for example, aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, for example, calcium cyanide, potassium cyanide and sodium cyanide. (25) Inhibitors of mitochondrial complex II electron transport, such as, for example, beta-ketonitrile derivatives, for example, cyanopyrraphen and cyflumethophene and carboxanilides, such as, for example, pirilubumide. (28) Ryanodine receptor modulators, such as, for example, diamides, for example, chlorantraniliprole, cyantraniliprole and flubendiamide, other active compounds such as, for example, afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionate, chlorprolethrin, cryolite, cyclaniloprole, cycloxapride, cyhalodiamide, dichlormomethiothiaz, dicofol, epsilon-methofluthrin, epsilon-momfluthrin, flomethoquine, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexaphone, fluopiram, fluralaner, fluxamethamide, fufenozide, guadipyr, heptafluthrin, imidaclothiaz, iprodione, kappa-Bifentrine, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, pyridalyl, pyrifluquinazon, pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Thioxazafen, Thiofluoximate, Triflumezopyrim and iodomethane;In addition to preparations based on Bacillus firmus (I1582, BioNeem, Votivo), the following compounds are also included: 1-{2-fluoro-4-methyl-5[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from document WO2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2en-1-yl]-5-fluorospiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from document WO2003 / 106457) (CAS 637360-23-7), 2-chloro-N-[2-{1Petition 870250043647, dated 05 / 27 / 2025, page 74 / 149; 71 / 125 [(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from document WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diasaespiro[4,5]dec-3-en-2-one (known from document WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diasaespiro[4.5]dec-3-en-4-yl ethyl carbonate (known from document EP2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from document WO2004 / 099160) (CAS 792914-58-0), PF1364 (known from document JP2010 / 018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from document WO2012 / 029672) (CAS 1363400-41-2), (3E)-3-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from document WO2013 / 144213) (CAS 1461743-15-6),N-[3(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol5-carboxamida (according to document WO2010 / 051926) (CAS 1226889-14-0), 5bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazol-3carboxamida (according to document CN103232431) (CAS 1449220-44-3), 4-[5-(3, 5-dichlorophenyl)-4,5-di-hidro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl- N-(cis 1 -oxido-3-thietanil)-benzamida, 4-[5-(3,5-dichlorophenyl)-4,5-di-hidro-5(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans -1 -oxido-3-thietanil)benzamida and 4-[(5 S )-5-(3,5-dichlorophenyl)-4,5-di-hidro-5-(trifluoromethyl)-3isoxazolyl]-2-methyl-N-(cis -1 -oxido-3-thietanil)benzamida (conhecido do documento WO 2013 / 050317 A1) (CAS 1332628-83-7), N-[3-chloro-1-(3pyridinyl)-1 H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamida, (+)-N-[3-chloro-1 -(3-pyridinyl)-1 H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1Hpyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide (known from WO 2013 / 162715 A2, WO 2013 / 162716 A2, Petition 870250043647, dated 05 / 27 / 2025, page 75 / 149 72 / 125 US 2014 / 0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]1H-pyrazol-3-carbonitrile (known from CN document 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-carboxamide, (Liudaibenjiaxuanan, known from CN document 103109816 A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-Pyrazol-5-carboxamide (known from document WO 2012 / 034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-carboxamide (known from document WO 2011 / 085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1 -yl)oxy]phenoxy]propoxy]-2-methoxy-6(trifluoromethyl)-pyrimidine (known from document CN 101337940 A) (CAS 1108184-52-6);(2 E)- and 2( Z )-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (known from document CN 101715774 A) (CAS 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylcyclopropanecarboxylic acid ester (known from document CN 103524422 A) (CAS 1542271-46-4); methyl ester of (4aS)-7-chloro-2,5-dihydro-2[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2e][1,3,4]oxadiazine-4a(3H)-carboxylic acid (known from the document; CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-, 1 -[ N-[4-[1-[4-(1, 1,2,2,2-pentafluoroethoxy)phenyl]-1 H -1,2,4-triazol-3-yl]phenyl] carbamate]-α-L-mannopyranose (known from US document 2014 / 0275503 A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3,2,1 Petition 870250043647, dated 05 / 27 / 2025, p. 76 / 149 73 / 125 ]octane (CAS 1253850-56-4), (8-anti )-8-(2-cyclopropylmethoxy-4trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1 ]octane (CAS 933798-27-7), (8-syn )-8-(2-cyclopropylmethoxy-4trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1] octane (according to document WO 2007040280 A1, WO 2007040282 A1) (CAS 934001 -66-8), N-[3-chloro-1 -(3-piridinil)-1 H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3trifluoropropyl)thio]-propanamida (conhecido do documento WO 2015 / 058021 A1, WO 2015 / 058028 A1) (CAS 1477919-27-9) e N-[4-(aminothioxometil)-2-metil-6[(metilamino)carbonyl]phenil]-3-bromo-1-(3-chloro-2-piridinil)-1H-pyrazol-5-carboxamida (conhecido do documento CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-il) -4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (according to WO document 2013 / 115391 A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hidróxi-8-metóxi1-methyl-1,8-diasaespiro[4.5]dec-3-en-2-ona (confirmed in WO document 2010 / 066780 A1, WO 2011 / 151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diasaespiro[4,5]decane-2,4-dione (known from document WO 2014 / 187846 A1) (CAS 1638765-58-8), ethyl ester of 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diasaespiro[4,5]dec-3en-4-yl-carbonic acid (known from document WO 2010 / 066780 A1, WO 2011 / 151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridinyl)methyl]2(1H)-pyridinilylidene]-2,2,2-trifluoroacetamide (known from document DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinilylidene]-2,2,2-trifluoroacetamide, (known from document WO 2016005276 A1) (CAS 1689566-03-7), [N(Z )]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)pyridinylidene]-2,2,2-trifluoroacetamide, (CAS 1702305-40-5), 3-endo 3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy] Petition 870250043647, dated 05 / 27 / 2025, page 77 / 149 74 / 125 9-azabicyclo[3,3,1]nonane (known from WO 2011 / 105506 A1, WO 2016 / 133011 A1) (CAS 1332838-17-1).

[0159] Examples of plant protection agents that can be mixed with compounds of formula (I) and compositions comprising them are, for example, benoxacor, cloquintocet (-mexil), ciometrinil, ciprosulfamide, dichlormid, fenclorazol (-ethyl), fenclorim, flurazol, fluxofenim, furilazol, isoxadifen (-ethyl), mefenpir (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)1-oxa-4-asaespiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0160] Examples of herbicides that can be mixed with compounds of formula (I) and compositions comprising them are:

[0161] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, aloxidim, aloxidim-sodium, ametryn, amicarbazone, amidochlor, amidosulfurone, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilophos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclone, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispiribac, bispiribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxinil, bromoxinyl-butyrate, potassium, heptanoate, and octanoate, busoxinone, butaclor, butafenacil, butamifos, butenaclor, butralin, butroxidim, butylate, cafenstrole, carbetamid, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol,chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfurone, clacifos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopiralid, Petition 870250043647, dated 05 / 27 / 2025, pp. 78 / 149 75 / 125 cloransulam, cloransulam-methyl, cumiluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxidim, cihalofop, cihalofop-butyl, ciprazine, 2,4-D, 2,4-D-butyl, -butyl, -dimethylammonium, -diolamin, -ethyl, -2-ethylhexyl, -isobutyl, iso-octyl, -isopropylammonium, -potassium, -triisopropanolammonium, and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, -iso-octyl, -potassium, and -sodium, daimuron (dimron), dalapon, dazomet, n-decanol, desmedifam, detosylpyrazolate (DTP), dicamba, diclobenyl, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyrsodium, dimefuron, dimepiperate, dimethachlor, dimethamethrin, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, difenamid, diquat, diquatdibromid, dithiopyr, diuron, DNOC, endotal, EPTC, sprocarb,etalfluralin, etametsulfurone, etametsulfuron-methyl, ethiozin, etofumesate, ethoxy-phen, ethoxy-phenethyl, ethoxy-sulfuron, etobenzanid, F-9600, F-5231, i.e., N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethanesulfonamide, F-7967, i.e., 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxapropethyl, fenoxaprop-P-ethyl, fenoxasulfone, phenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycophene, fluoroglycophene-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuronmethyl-sodium, fluridone, flurochloridone,fluroxypyr, fluroxypyr-meptyl, flurtamone, flutiacet, flutiacet-methyl, fomesafen, fomesafen-sodium, foramsulfurone, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium Petition 870250043647, dated 05 / 27 / 2025, pp. 79 / 149 76 / 125 sodium, e-trimesium, H-9201, i.e., O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halauxifene, halauxifene-methyl, halosaphene, halosulfurone, halosulfurone-methyl, haloxifop, haloxifop-P, haloxifop-ethoxyethyl, haloxifop-P-ethoxyethyl, haloxifop-methyl, haloxifop-P-methyl, hexazinone, HW-02, i.e., 1-(dimethoxyphosphoryl) ethyl-(2,4-dichlorophenoxy)acetate, imazametabenz, imazametabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyrisopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-imonium, imazosulfurone, indanophane, indaziflam, iodosulfurone, iodosulfurone-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and -sodium, ipfencarbazone, isoproturone, isourone, isoxaben, isoxaflutole, karbutylate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactophene, lenacil, linurone, MCPA, MCPA-butotil, -dimethylammonium,-2-ethylhexyl, -isopropylammonium, -potassium, and -sodium, MCPB, MCPB-methyl, -ethyl, and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, dimethylammonium, -2-ethylhexyl, and -potassium, mefenacet, mefluidide, mesosulfurone, mesosulfuron-methyl, mesotrione, metabenzthiazurone, metam, metamifop, metamitron, metazachlor, metazosulfuron, metabenzthiazuron, methiopyrsulfurone, methiozoline, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, methoxurone, metribuzin, metsulfurone, metsulfuron-methyl, molinat, monolinurone, monosulfurone, monosulfurone-ester, MT-5950, i.e., N-(3-chloro-4-isopropylphenyl)-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)methanone, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamurone, oryzalin, oxadiargile, oxadiazone, oxasulfurone, oxaziclomefon, oxyfluorfen, paraquat,paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, petoxamid, petroleum oils, phenmedifam, picloram, picolinafen, pinoxaden, piperofos, pretilachlor, primisulfuron, primisulfuron, Petition 870250043647, dated 05 / 27 / 2025, pp. 80 / 149 77 / 125 methyl, prodiamine, profoxidim, prometon, prometrin, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazona, propoxycarbazona-sodica, propyrisulfurona, propizamida, prosulfocarbe, prosulfuron, pyraclonil, piraflufen, piraflufen-ethyla, pyrasulfotole, pyrazolinate (pyrazolate), pyrazosulfurone, pyrazosulfuron-ethyl, pyrazoxyfeno, piribambenz, piribambenzisopropyl, piribambenz-propyl, piribenzoxim, piributicarbe, piridafol, pyridate, piriftalid, piriminobac, piriminobac-methyla, pirimisulfan, piritiobac, pirithiobac-sodium, pyroxasulfona, piroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-etila, quizalofop-P, quizalofop-P-etila, quizalofop-P-tefurila, rimsulfuron, saflufenacil, setoxidim, siduron, simazine, simethrin, SL-261, sulcotrion, sulfentrazona, sulfometurone, sulfometuron-methyla, sulfosulfurona, SYN-523, SYP-249, ou seja, 5-[2chloro-4-(trifluoromethyl)phenóxi]-2-nitrobenzoato de 1 -ethóxi-3-methyl-1 -oxobut-3-en-2-ila, SYP-300,i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxidim, terbacil, terbucarb, terbumetone, terbuthylazine, terbutrin, tenylchlor, thiazopyr, thiencarbazone, thiencarbazonemethyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenacil, tolpiralate, topramezone, tralkoxydim, triafamone, trialate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, that is, 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:, Petition 870250043647, dated 05 / 27 / 2025, page 81 / 149 78 / 125

[0162] Examples of plant growth regulators are: Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancimidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, chlorprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetraline, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, paclobutrazol, N-(2-phenylethyl)-beta-alanine, N-phenylphthalamic acid, pro-hexadione, pro-hexadione-calcium, pro-hydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazurone, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P. Methods and Use

[0163] The compounds of formula (I) and the compositions comprising them have potent microbicidal activity. They can be used to control undesirable microorganisms, such as fungi and undesirable bacteria. They can be particularly useful in protecting crops (they control microorganisms that cause plant diseases) or in protecting materials (e.g., industrial materials, wood, storage products), as described in more detail below. More specifically, the compounds of formula (I) and the compositions comprising them can be used to protect seeds, seeds in Petition 870250043647, dated 05 / 27 / 2025, page 82 / 149 79 / 125 germination, emerged seedlings, plants, plant parts, fruits, harvested products and / or the soil in which the plants grow against undesirable microorganisms.

[0164] Control or controlling, as used in this document, encompasses the protective, curative, and eradicative treatment of undesirable microorganisms. Undesirable microorganisms may be pathogenic bacteria, pathogenic viruses, pathogenic oomycetes, or pathogenic fungi, more specifically phytopathogenic bacteria, phytopathogenic viruses, phytopathogenic oomycetes, or phytopathogenic fungi. As detailed in this document below, these phytopathogenic microorganisms are the causal agents of a wide spectrum of plant diseases.

[0165] More specifically, the compounds of formula (I) and compositions comprising them can be used as fungicides. For the purpose of this descriptive report, the term fungicide refers to a compound or composition that can be used in crop protection for the control of undesirable fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and / or for the control of Oomycetes, with more preference for the control of Basidiomycetes (causative agents of rust diseases).

[0166] The present invention also relates to a method for controlling undesirable microorganisms, such as phytopathogenic fungi, oomycetes and bacteria, comprising the step of applying at least one compound of formula (I) or at least a composition comprising the same to the microorganisms and / or their habitats (to plants, plant parts, seeds, fruits or to the soil in which the plants grow).

[0167] Typically, when the compound and composition of the invention are used in curative or protective methods to control phytopathogenic fungi and / or phytopathogenic oomycetes, an effective and plant-compatible amount is applied to the plants, plant parts, fruits, seeds, or the soil or substrates in which the plants grow. Suitable substrates that can be used for cultivation Petition 870250043647, dated 05 / 27 / 2025, page 83 / 149 80 / 125 plant substrates include inorganic-based substrates such as mineral wool, in particular rock wool, perlite, sand or gravel; organic substrates such as peat, pine bark or sawdust; and petroleum-based substrates such as polymer foams or plastic microspheres. Effective and plant-compatible quantity means a quantity that is sufficient to control or destroy fungi present or likely to appear in the growing area and that does not cause any appreciable symptoms of phytotoxicity to said crops. Such quantity may vary within a wide range depending on the fungus to be controlled, the type of crop, the growth stage of the crop, the climatic conditions and the respective compound or composition of the invention used. This quantity can be determined by systematic field trials that are within the capabilities of one skilled in the art. Plants and plant parts

[0168] The compounds of formula (I) and the compositions comprising them may be applied to any plants or parts of plants.

[0169] Plants means all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants). Cultivated plants may be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including genetically modified plants (GMOs or transgenic plants) and plant cultivars that are protectable and unprotectable by plant breeder rights.

[0170] Plant parts are understood to be all parts and organs of plants above and below ground, such as shoots, leaves, flowers and roots, examples of which include leaves, needles, stems, trunks, flowers, fruiting bodies, fruits and seeds, and also roots, tubers and rhizomes. Plant parts also include material Petition 870250043647, dated 05 / 27 / 2025, page 84 / 149 81 / 125 harvested and vegetative and generative propagation material, for example, cuttings, tubers, rhizomes, seedlings and seeds.

[0171] Plants that can be treated according to the methods of the invention include the following: cotton, flax, vine, fruits, vegetables, such as Rosaceae sp. (e.g., pome fruits, such as apples and pears, but also stone fruits, such as apricots, cherries, almonds and peaches, and soft fruits, such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g., banana trees and plantations), Rubiaceae sp. (e.g., coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (e.g., lemons, oranges and grapefruits); Solanaceae sp. (e.g., tomatoes), Liliaceae sp., Asteraceae sp. (e.g., lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (e.g., cucumber), Alliaceae sp. (e.g., leek, onion), Papilionaceae sp. (e.g., peas); major cultivated plants, such as Gramineae sp.(e.g., corn, grass, cereals such as wheat, rye, rice, barley, oats, millet, and triticale), Asteraceae sp. (e.g., sunflower), Brassicaceae sp. (e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and rapeseed, mustard, horseradish, and watercress), Fabaceae sp. (e.g., beans, peanuts), Papilionaceae sp. (e.g., soybeans), Solanaceae sp. (e.g., potatoes), Chenopodiaceae sp. (e.g., sugar beet, fodder beet, Swiss chard, beet); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.

[0172] In some preferred embodiments, wild plant species and plant cultivars, or those obtained by conventional methods of biological improvement, such as crossing or fusion of protoplasts, and also their parts are treated according to the methods of the invention. Petition 870250043647, dated 05 / 27 / 2025, page 85 / 149 82 / 125

[0173] In some other preferred embodiments, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate, in combination with conventional methods (Genetically Modified Organisms), and their parts are treated according to the methods of the invention. More preferably, plants of plant cultivars that are commercially available or in use are treated according to the invention. By plant cultivars is meant plants that possess new properties (traits) and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They may be cultivars, varieties, bio- or genotypes.

[0174] The methods according to the invention can be used in the treatment of genetically modified organisms (GMOs), for example, plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term heterologous gene essentially means a gene that is supplied or assembled outside the plant and, when introduced into the nucleus, the chloroplast or mitochondrial genome, gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) that are present in the plant (using, for example, antisense technology, co-suppression technology, RNA interference technology - RNAi or microRNA technology - miRNA). A heterologous gene located in the genome is also called a transgene.A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

[0175] Plants and plant cultivars that can be treated by the methods described above include all plants that have genetic material that confers useful and particularly advantageous characteristics to those plants (whether obtained through reproduction and / or by biotechnological means). Petition 870250043647, dated 05 / 27 / 2025, page 86 / 149 83 / 125

[0176] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are resistant to one or more biotic stresses, i.e., said plants show better defense against animal and microbial pests, such as nematodes, insects, mites, fungi, bacteria, viruses and / or phytopathogenic viroids.

[0177] Plants and plant cultivars that can be treated by the methods disclosed above include those plants that are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, exposure to cold temperatures, exposure to heat, osmotic stress, flooding, increased soil salinity, increased exposure to minerals, exposure to ozone, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.

[0178] Plants and plant cultivars that can be treated by the methods disclosed above include those plants characterized by improved yield characteristics. The increase in yield in said plants may be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, improved carbon assimilation, improved photosynthesis, higher germination efficiency and accelerated maturation.Yield can also be affected by improved plant architecture (under stress and non-stress conditions), including, but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, number and distance of internodes, root growth, seed size, fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed mass, improved seed filling, reduced seed dispersal, reduced pod dehiscence, and lodging resistance. Other yield characteristics include seed composition, such as content. Petition 870250043647, dated 05 / 27 / 2025, page 87 / 149 84 / 125 of carbohydrates and composition, for example, cottonseed or starch, protein content, oil content and composition, nutritional value, reduction of antinutritional compounds, improved processability and better storage stability.

[0179] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are hybrid plants that already express the characteristic of heterosis or hybrid vigor which generally results in higher yield, vigor, health and resistance to biotic and abiotic stresses.

[0180] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that are herbicide-tolerant plants, that is, plants made tolerant to one or more given herbicides. These plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such herbicide tolerance.

[0181] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that are insect-resistant transgenic plants, that is, plants made resistant to attack by certain target insects. These plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such insect resistance.

[0182] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that are tolerant to abiotic stresses. These plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such stress resistance.

[0183] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that show quantity Petition 870250043647, dated 05 / 27 / 2025, pp. 88 / 149 85 / 125 altered, quality and / or storage stability of the harvested product and / or altered properties of specific ingredients of the harvested product.

[0184] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars, such as cotton plants, with altered fiber characteristics. These plants can be obtained by genetic transformation or by selection of plants that contain a mutation that confers such altered fiber characteristics.

[0185] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars, such as rapeseed or related Brassica plants, with altered oil profile characteristics. These plants can be obtained by genetic transformation or by selection of plants that contain a mutation that confers such altered oil profile characteristics.

[0186] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars, such as rapeseed or related Brassica plants, with altered seed-breaking characteristics. These plants can be obtained by genetic transformation or by selection of plants that contain a mutation that confers such altered seed-breaking characteristics and include plants, such as rapeseed, with delayed or reduced seed-breaking.

[0187] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars, such as tobacco plants, with altered post-translational protein modification patterns. Pathogens and diseases Petition 870250043647, dated 05 / 27 / 2025, pp. 89 / 149 86 / 125

[0188] The methods disclosed above can be used to control microorganisms, in particular, phytopathogenic microorganisms, such as phytopathogenic fungi, causing diseases such as: Diseases caused by powdery mildew pathogens, such as Blumeria species (e.g., Blumeria graminis), Podosphaera species (e.g., Podosphaera leucotricha), Sphaerotheca species (e.g., Sphaerotheca fuliginea), and Uncinula species (e.g., Uncinula necator); Diseases caused by rust disease pathogens, such as species of Gymnosporangium (e.g., Gymnosporangium sabinae), species of Hemileia (e.g., Hemileia vastatrix), species of Phakopsora (e.g., Phakopsora pachyrhizi or Phakopsora meibomiae), species of Puccinia (e.g., Puccinia recondita, Puccinia graminis, or Puccinia striiformis), species of Uromyces (e.g., Uromyces appendiculatus); Diseases caused by pathogens from the Oomycetes group, such as Albugo species (e.g., Albugo candida), Bremia species (e.g., Bremia lactucae), Peronospora species (e.g., Peronospora pisi or P. brassicae), Phytophthora species (e.g., Phytophthora infestans), Plasmopara species (e.g., Plasmopara viticola), Pseudoperonospora species (e.g., Pseudoperonospora humuli or Pseudoperonospora cubensis), and Pythium species (e.g., Pythium ultimum); Leaf spot diseases and leaf wilt diseases caused, for example, by Alternaria species (e.g., Alternaria solani), Cercospora species (e.g., Cercospora beticola), Cladiosporium species (e.g., Cladiosporium cucumerinum), Cochliobolus species (e.g., Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus), Colletotrichum species (e.g., Colletotrichum lindemuthanium), Cycloconium species (e.g., Cycloconium oleaginum), Petition 870250043647, dated 05 / 27 / 2025, pp. 90 / 149 87 / 125 species of Diaporthe (e.g., Diaporthe citri), species of Elsinoe (e.g., Elsinoe fawcettii), species of Gloeosporium (e.g., Gloeosporium laeticolor), species of Glomerella (e.g., Glomerella cingulate), species of Guignardia (e.g., Guignardia bidwelli), species of Leptosphaeria (e.g., Leptosphaeria maculans), species of Magnaporthe (e.g., Magnaporthe grisea), species of Microdochium (e.g., Microdochium nivale), species of Mycosphaerella (e.g., Mycosphaerella graminicola, Mycosphaerella arachidicola, or Mycosphaerella fijiensis), species of Phaeosphaeria (e.g., Phaeosphaeria nodorum), species of Pyrenophora (e.g., Pyrenophora teres or Pyrenophora tritici repentis), species of Ramularia (e.g. Ramularia collo-cygni or Ramularia areola), Rhynchosporium species (e.g. Rhynchosporium secalis), Septoria species (e.g. Septoria apii or Septoria lycopersici),Stagonospora species (e.g., Stagonospora nodorum), Typhula species (e.g., Typhula incarnate), Venturia species (e.g., Venturia inaequalis), root and stem diseases caused, for example, by Corticium species (e.g., Corticium graminearum), Fusarium species (e.g., Fusarium oxysporum), Gaeumannomyces species (e.g., Gaeumannomyces graminis), Plasmodiophora species (e.g., Plasmodiophora brassicae), Rhizoctonia species (e.g., Rhizoctonia solani), Sarocladium species (e.g., Sarocladium oryzae), Sclerotium species (e.g., Sclerotium oryzae), Tapesia species (e.g., Tapesia acuformis), Thielaviopsis species (e.g., Thielaviopsis basicola); Diseases of the ear and panicle (including corn ears) caused, for example, by Alternaria species (e.g., Alternaria spp.), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium cladosporioides), Claviceps species (e.g., Claviceps Petition 870250043647, dated 05 / 27 / 2025, pp. 91 / 149 88 / 125 purpurea), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Monographella species (e.g., Monographella nivalis), Stagnospora species (e.g., Stagnospora nodorum); Diseases caused by smut fungi, for example species of Sphacelotheca (e.g., Sphacelotheca reiliana), species of Tilletia (e.g., Tilletia caries or Tilletia controversa), species of Urocystis (e.g., Urocystis occulta), species of Ustilago (e.g., Ustilago nuda); Fruit rot caused, for example, by Aspergillus species (e.g., Aspergillus flavus), Botrytis species (e.g., Botrytis cinerea), Penicillium species (e.g., Penicillium expansum or Penicillium purpurogenum), Rhizopus species (e.g., Rhizopus stolonifer), Sclerotinia species), Verticillium species (e.g., Verticillium alboatrum); Seed-borne and soil-borne rot and wilt diseases, as well as seedling diseases, caused, for example, by Alternaria species (e.g., Alternaria brassicicola), Aphanomyces species (e.g., Aphanomyces euteiches), Ascochyta species (e.g., Ascochyta lentis), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium herbarum), Cochliobolus species (e.g., Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium)), Colletotrichum species (e.g., Colletotrichum coccodes), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Macrophomina species (e.g., Macrophomina phaseolina), Microdochium species (e.g., Microdochium nivale), Monographellas species (e.g. Monographella nivalis), Penicillium species (e.g. Penicillium expansum),Phoma species (e.g., Phoma lingam), Phomopsis species (e.g., Phomopsis sojae), Phytophthora species, Petition 870250043647, dated 05 / 27 / 2025, pp. 92 / 149 89 / 125 (e.g., Phytophthora cactorum), Pyrenophora species (e.g., Pyrenophora gramineae), Pyricularia species (e.g., Pyricularia oryzae), Pythium species (e.g., Pythium ultimum), Rhizoctonia species (e.g., Rhizoctonia solani), Rhizopus species (e.g., Rhizopus oryzae), Sclerotium species (e.g., Sclerotium rolfsii), Septoria species (e.g., Septoria nodorum), Typhula species (e.g., Typhula incarnate), Verticillium species (e.g., Verticillium dahlia); Cancers, galls, and witches' broom caused, for example, by species of Nectria (e.g., Nectria galligena); Wilting diseases caused, for example, by Monilinia species (e.g., Monilinia laxa); Deformations of leaves, flowers and fruits caused, for example, by Exobasidium species (e.g., Exobasidium vexans), Taphrina species (e.g., Taphrina deformans); Degenerative diseases in woody plants, caused, for example, by species of Esca (e.g., Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea), species of Ganoderma (e.g., Ganoderma boninense); Diseases of flowers and seeds caused, for example, by species of Botrytis (e.g., Botrytis cinerea); Plant tuber diseases caused, for example, by Rhizoctonia species (e.g., Rhizoctonia solani), Helminthosporium species (e.g., Helminthosporium solani); Diseases caused by bacterial pathogens, for example, Xanthomonas species (e.g., Xanthomonas campestris pv. oryzae), Pseudomonas species (e.g., Pseudomonas syringae pv. lachrymans), Erwinia species (e.g., Erwinia amylovora). Petition 870250043647, dated 05 / 27 / 2025, pp. 93 / 149 90 / 125 In particular, the compounds of formula (I) and the compositions comprising them are effective in controlling phytopathogenic fungi that cause rust diseases. Seed Treatment

[0189] The method for controlling undesirable microorganisms can be used to protect seeds from phytopathogenic microorganisms, such as fungi.

[0190] The term seed(s), as used in this document, includes dormant seed, prepared seed, pre-germinated seed and seed with emerged roots and leaves.

[0191] Thus, the present invention also relates to a method for protecting seeds and / or crops from undesirable microorganisms, such as bacteria or fungi, comprising the step of treating the seeds with one or more compounds of formula (I) or a composition comprising the same. Treating seeds with the compound(s) of formula (I) or a composition comprising the same protects not only the seeds from phytopathogenic microorganisms, but also the germinating plants, the emerged seedlings and the plants after emergence.

[0192] Seed treatment can be carried out before sowing, at the time of sowing or immediately after.

[0193] When seed treatment is carried out before sowing (for example, so-called seed applications), seed treatment may be carried out as follows: the seeds may be placed in a mixer with a desired amount of compound(s) of formula (I) or a composition comprising the same (as such or after dilution), the seeds and the compound(s) of formula (I) or the composition comprising the same are mixed until a homogeneous distribution on the seeds is achieved. If necessary, the seeds may be dried. Petition 870250043647, dated 05 / 27 / 2025, pp. 94 / 149 91 / 125

[0194] The invention also relates to seeds treated with one or more compounds of formula (I) or a composition comprising the same. As stated before, the use of treated seeds allows not only to protect the seeds before and after sowing from undesirable microorganisms, such as phytopathogenic fungi, but also to protect germinating plants and young seedlings that emerge from said treated seeds. Much of the damage to agricultural plants caused by harmful organisms is triggered by seed infection before sowing or after plant germination. This phase is particularly critical, since the roots and buds of the growing plant are particularly sensitive, and even minor damage can result in the death of the plant.

[0195] Therefore, the present invention also relates to a method for protecting seeds, germinating plants and emerged seedlings, more generally to a method for protecting the crop from phytopathogenic microorganisms, comprising the step of using seeds treated with one or more compounds of formula (I) or a composition comprising the same.

[0196] Preferably, the seed is treated in a state where it is sufficiently stable so that no damage occurs during the course of treatment. In general, seeds can be treated at any time between harvest and shortly after sowing. It is common to use seeds separated from the plant and freed from the ears, husks, stems, skins, hairs or fruit pulp. For example, it is possible to use harvested, cleaned and dried seeds with a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds that, after drying, for example, have been treated with water and then dried again, or seeds shortly after initiation, or seeds stored in prepared conditions, or pre-germinated seeds, or seeds sown in nursery trays, ribbons or paper. Petition 870250043647, dated 05 / 27 / 2025, pp. 95 / 149 92 / 125

[0197] The amount of compound(s) of formula (I) or composition comprising the same applied to the seed is typically such that seed germination is not impaired, or the resulting plant is not damaged. This must be ensured particularly in the case where the active ingredients exhibit phytotoxic effects at certain application rates. The intrinsic phenotypes of transgenic plants must also be taken into account when determining the amount of compound(s) of formula (I) or composition comprising the same to be applied to the seed, in order to achieve optimal seed and plant germination protection with a minimum amount of compound(s) of formula (I) or composition comprising the same being employed.

[0198] As indicated above, the compounds of formula (I) may be applied as such directly to the seeds, i.e., without the use of any other components and without dilution, or a composition comprising the compounds of formula (I) may be applied. Preferably, the compositions are applied to the seed in any suitable form. Examples of suitable formulations include solutions, emulsions, suspensions, powders, foams, pastes, or combined with other seed coating compositions, such as film-forming materials, pelleting materials, fine iron or other metal powders, granules, inactivated seed coating material, and also ULV formulations. The formulations may be ready-to-use formulations or may be concentrated and need to be diluted before use.

[0199] These formulations are prepared in a known manner, for example, by mixing the active ingredient or mixture thereof with usual additives, for example, usual extenders and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins, and also water. Petition 870250043647, dated 05 / 27 / 2025, pp. 96 / 149 93 / 125

[0200] These formulations are prepared in a known manner by mixing the active ingredients or combinations of active ingredients with usual additives, for example, usual extenders and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins, and also water.

[0201] Useful colorants that may be present in seed treatment formulations are all the usual colorants for such purposes. It is possible to use pigments, which are moderately soluble in water, or colorants, which are soluble in water. Examples include the colorants known by the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1. Useful wetting agents that may be present in seed treatment formulations are all substances that promote wetting and that are conventionally used for the formulation of active agrochemical ingredients. Preferably usable are alkylnaphthalenesulfonates, such as di-isopropyl- or di-isobutylnaphthalenesulfonates. Useful dispersants and / or emulsifiers that may be present in seed treatment formulations are all non-ionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients.Nonionic or anionic dispersants, or mixtures of nonionic or anionic dispersants, are preferable. Useful nonionic dispersants include especially ethylene oxide / propylene oxide block polymers, alkyl ethers and tristrirylphenol polyglycol ether, and phosphate or sulfate derivatives thereof. Suitable anionic dispersants are especially lignosulfonates, polyacrylic acid salts and aryl sulfonate / formaldehyde condensates. Antifoaming agents that may be present in seed treatment formulations are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone and magnesium stearate antifoaming agents may be used preferentially. Preservatives that may be present... Petition 870250043647, dated 05 / 27 / 2025, pp. 97 / 149 94 / 125 present in seed treatment formulations are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and hemiformal benzyl alcohol. Secondary thickeners that may be present in seed treatment formulations are all substances usable for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays, and finely divided silica. Adhesives that may be present in seed treatment formulations are all common binders usable in seed treatment products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tylose.

[0202] The compounds of formula (I) and the compositions comprising them are suitable for protecting seeds of any variety of plant that is used in agriculture, in greenhouses, in forests or in horticulture. More particularly, the seeds are those of cereals (such as wheat, barley, rye, millet, triticale, and oats), rapeseed, maize, cotton, soybean, rice, potato, sunflower, beans, coffee, peas, beet (e.g., sugar beet and fodder beet), peanuts, vegetables (such as tomato, cucumber, onion and lettuce), lawns and ornamental plants. Of particular importance is the treatment of seeds of wheat, soybean, rapeseed, maize and rice.

[0203] The compounds of formula (I) or compositions comprising them can be used for the treatment of transgenic seeds, in particular seeds of plants capable of expressing a protein that acts against pests, herbicide damage or abiotic stress, thereby increasing the protective effect. Synergistic effects may also occur in interaction with substances formed by expression. Application Petition 870250043647, dated 05 / 27 / 2025, pp. 98 / 149 95 / 125

[0204] The compound of formula (I) can be applied as such, or for example, in the form of ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, powders, soluble granules, diffusion granules, suspoemulsion concentrates, natural products impregnated with the compound of formula (I), synthetic substances impregnated with the compound of formula (I), fertilizers or microencapsulations in polymeric substances.

[0205] Application is carried out in a usual manner, for example, by watering, spraying, atomizing, diffusion, dusting, foaming, spreading and the like. It is also possible to implement the compound of formula (I) by the ultra-low volume method, via drip irrigation system or irrigation application, to apply it in the furrow or inject it into the stem or trunk of the soil. It is also possible to apply the compound of formula (I) by means of a wound seal, ink or other wound dressing.

[0206] The effective and plant-compatible amount of the compound of formula (I) that is applied to plants, plant parts, fruits, seeds or soil will depend on several factors, such as the compound / composition employed, the object of treatment (plant, plant part, fruit, seed or soil), the type of treatment (spraying, dusting, seed treatment), the purpose of the treatment (curative and protective), the type of microorganisms, the stage of development of the microorganisms, the sensitivity of the microorganisms, the stage of growth of the crop and the environmental conditions.

[0207] When the compound of formula (I) is used as a fungicide, application rates can vary within a relatively wide range, depending on the type of application. For the treatment of plant parts, such as leaves, the application rate can vary from 0.1 to 10,000 g / ha, preferably from 10 to 1,000 g / ha, more preferably from 50 to 300 g / ha (in the case of irrigation or drip irrigation, it is even possible to reduce the application rate, especially when using Petition 870250043647, dated 05 / 27 / 2025, pp. 99 / 149 96 / 125 inert substrates such as rock wool or perlite). For seed treatment, the application rate can vary from 0.1 to 200 g per 100 kg of seeds, preferably from 1 to 150 g per 100 kg of seeds, more preferably from 2.5 to 25 g per 100 kg of seeds, and even more preferably from 2.5 to 12.5 g per 100 kg of seeds. For soil treatment, the application rate can vary from 0.1 to 10,000 g / ha, preferably from 1 to 5,000 g / ha.

[0208] These application rates are merely examples and are not intended to limit the scope of the present invention. Material Protection

[0209] The compound and composition of the invention can also be used in the protection of materials, especially for the protection of industrial materials against attack and destruction by undesirable microorganisms.

[0210] In addition, the compound and composition of the invention can be used as anti-fouling compositions, alone or in combination with other active ingredients.

[0211] Industrial materials in the present context are understood to mean inanimate materials that have been prepared for use in industry. For example, industrial materials that must be protected from microbial alteration or destruction may include adhesives, glues, paper, wallpaper and cardboard, textiles, carpets, leather, wood, fibers and fabrics, paints and plastic articles, refrigeration lubricants and other materials that may be infected or destroyed by microorganisms. Parts of production facilities and buildings, for example, cooling water circuits, cooling and heating systems and ventilation and air conditioning units, which may be damaged by the proliferation of microorganisms, may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, gums, paper and cardboard, leather, wood, Petition 870250043647, dated 05 / 27 / 2025, pp. 100 / 149 97 / 125 paints, cooling lubricants and heat transfer fluids, preferably wood.

[0212] The compound and composition of the invention can prevent adverse effects such as rotting, decomposition, discoloration, fading or mold formation.

[0213] In the case of wood treatment, the compound and composition of the invention can also be used against fungal diseases that can grow on or inside construction timber.

[0214] Construction timber means all types of wood species, and all types of timber products intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. In addition, the compound and composition of the invention can be used to protect objects that come into contact with salt or brackish water, especially hulls, screens, nets, buildings, moorings and signaling systems, against fouling.

[0215] The compound and composition of the invention can also be used to protect goods in storage. Storage goods are understood to be natural substances of plant or animal origin or their processed products of natural origin, for which long-term protection is desired. Storage goods of plant origin, for example, plants or parts of plants, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, wetting, crushing, grinding, pressing or roasting. Storage goods also include construction timber, whether unprocessed construction timber, such as construction timber for buildings, poles and electricity barriers, or in the form of finished products, such as furniture. Storage products of animal origin are, for example, raw hides, leather, skins and Petition 870250043647, dated 05 / 27 / 2025, pp. 101 / 149 98 / 125 hairs. The compound and composition of the invention can prevent adverse effects such as rotting, decomposition, discoloration, fading, or mold formation.

[0216] Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae, and slime molds. The compound and composition of the invention preferentially act against fungi, especially molds, wood-discoloring fungi, and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes, and Zygomycetes), and against slime molds and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Saccharomyces cerevisae.

[0217] Aspects of the present teaching can be better understood in the light of the following examples, which should not be interpreted as limiting the scope of the present teaching in any way. EXAMPLES

[0218] The following examples illustrate, in a non-limiting manner, the preparation and effectiveness of the compounds of formula (I) according to the invention. Synthesis of intermediates of formula (II) according to process P1 Petition 870250043647, dated 05 / 27 / 2025, pp. 102 / 149 99 / 125 4,4,4-Trifluoro-1-[4-(1H-imidazol-1-yl)phenyl]butane-1,3-dione

[0219] To a solution of 1-[4-(1H-imidazol-1-yl)phenyl]ethanone (200 mg, 1.1 mmol) in THF (2.8 ml) ethyl 2,2,2-trifluoroacetate (305 mg, 2.2 mmol) was added, followed by potassium tert-butoxide (2.2 ml, 2.2 mmol, 1 M in THF) dropwise at 0 °C. The reaction mixture was stirred for 1 h at room temperature. Aqueous hydrochloric acid solution (2.2 ml, 1 M) was then added. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure to obtain the title compound (262 mg, 80% purity, 69% yield), which was used in the next step without further purification. Synthesis of intermediates of formula (V) -(4-Bromo-2-fluorophenyl)-4,4,4-trifluorobutane-1,3-dione

[0220] A solution of 4-bromo-2-fluoroacetophenone (25 g, 1 eq) and sodium hydride (5.99 g, 1.3 eq, 60%) in degassed THF (200 ml) was stirred at 0 °C for 30 min. Ethyl 2,2,2-trifluoroacetate (21.3 g, 1.3 eq) was added in portions over 5 min at 0 °C. The reaction mixture was then stirred at room temperature for 3 h. Water and ice (400 ml) were then added. The aqueous layer was extracted. Petition 870250043647, dated 05 / 27 / 2025, pp. 103 / 149 100 / 125 three times with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to obtain the title compound (25 g), which was used in the next step without further purification. 3-(4-Bromo-2-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol

[0221] Hydroxylamine hydrochloride (3.68 g, 1.2 eq) was added to a solution of 1-(4-bromo-2-fluorophenyl)-4,4,4-trifluorobutane-1,3-dione (20 g, 1 eq) in acetic acid (100 ml). The reaction mixture was stirred for 3 ha at 120 °C. At room temperature, an ice-water mixture (300 ml) was added. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by reverse-phase chromatography to obtain the title compound (10.4 g, 50% yield) as a whitish solid. MS (ESI): 328 ([M+H]+) Synthesis of intermediates (VII) according to process P6 3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol

[0222] 3-(4-Bromophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (100 mg, 0.32 mmol), bis(pinacolato)diboron (123 mg, 0.48 mmol), [1,1Bis(diphenylphosphine)ferrocene]dichloropalladium(II) complex. dichloromethane (7.3 mg, 0.011 mmol) and Petition 870250043647, dated 05 / 27 / 2025, pp. 104 / 149 101 / 125 potassium acetate (95 mg, 0.97 mmol) was dissolved in degassed dioxane (2 ml). The mixture was stirred at 80 °C for 3 h, then cooled to room temperature and diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent: heptane / ethyl acetate) to obtain the title compound (95 mg, 78% yield) as a pale yellow honey. MS (ESI): 358 ([M+H]+) Synthesis of intermediates of formula (I) 3-[4-(1H-Imidazol-1-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (Compound I-034)

[0223] Hydroxylamine hydrochloride (72 mg, 1.03 mmol) was added to a solution of 4,4,4-trifluoro-1-[4-(1H-imidazol-1-yl)phenyl]butane-1,3-dione (261 mg, 0.74 mmol) in acetic acid (2.5 ml). The reaction mixture was stirred for 1 h at 100 °C. It was then poured into water and stirred for 15 min. The solid was removed by filtration and dried to obtain the title compound (103 mg, 46% yield). MS (ESI): 298 ([M+H]+) 3-[4-(1-Ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol Petition 870250043647, dated 05 / 27 / 2025, pp. 105 / 149 102 / 125

[0224] To 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (86 mg, 0.39 mmol) and Tetraquis(triphenylphosphine)palladium(0) (20 mg, 0.018 mmol) were added a solution of cesium carbonate (125 mg, 0.39 mmol) in water (1 ml) and a solution of 3-(4-bromophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (108 mg, 0.35 mmol) in 1,2-dimethoxyethane (3 ml). The mixture was stirred at 80 °C for 1 h, then cooled to room temperature. Water and dichloromethane were then added and the 2 layers were separated. The organic layer was filtered over a silica cartridge, eluted with dichloromethane, and evaporated. The residue was purified using preparative HPLC-MS (SunFire Waters, 30*150, 5 μm, eluent: acetonitrile / water (0.1% formic acid)) to obtain the title compound (25.7 mg, 23% yield). MS (ESI): 324 ([M+H]+) (5S)-3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro1,2-oxazol-5-yl acetate and (5R)-3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)4,5-dihydro-1,2-oxazol-5-yl (Compounds I-026 and I-041)

[0225] A mixture of 3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (100 mg, 0.31 mmol), acetic anhydride (471 mg, 4.6 mmol) and N,N-dimethylaminopyridine (75 mg, 0.62 mmol) in acetic acid (2 ml) was stirred for 6 h at 70 °C. The solvent was evaporated and the residue was dissolved in ethyl acetate, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography to obtain 3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-yl acetate (100 mg, 88% yield). The Petition 870250043647, dated 05 / 27 / 2025, pp. 106 / 149 Foram enantiomers 103 / 125 were separated on chiral SFC (CO2 / acetonitrile eluent) to obtain: isomer 1: Acetate of (5S)-3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)415-di-hydro-112-oxazol-5-yl or acetate of (5R)-3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5(trifluoromethyl)-415-di-hydro-112-oxazol-5-yla (Compound I-026) MS (ESI): 368 ([M+H]+) Rotation: +109.6° (c=0.68, MeOH, 25 °C, 589 nm) isomer 2: Acetate of (5S)-3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5-(trifluoromethyl)de-oxyl-oizo1-acyl-di-5 (5R)-3-[4-(1-ethyl-1H-pyrazol-4-yl)phenyl]-5(trifluoromethyl)-4i5-di-hydro-1i2-oxazol-5-yla (Compound I-041) MS (ESI): 368 ([M+H]+) Rotation: −109.6° (c=0.68, MeOH, 25 °C, 589 nm) 3-[4-(1-Ethyl-1 H-pyrazol-4-yl)-2-fluorophenyl]-5-(trifluoromethyl)-4i5-di-hydro-1i2oxazol-5-ol (Compound I-042)

[0226] 1-Ethyl-4-(4i4i5i5-tetramethyl-1i3i2-dioxaborolan-2-yl)-1H-pyrazole (75 mgi 0i35 mmol) 3-(4-bromo-2-fluorophenyl)-5-(trifluoromethyl)-4i5-dihydro-1i2-oxazol-5-ol (100 mgi 0i31 mmol) [1J-Bis (di-tert-butylphosphino)ferrocene]dichloropalladium (II) (9i9 mgi 0i015 mmol) and cesium carbonate (109 mgi 0i34 mmol) were dissolved in degassed dioxane (1.5 ml) and degassed water (0i5 ml). The mixture was stirred at 80 °C for 90 min and then cooled to room temperature and diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by... Petition 870250043647, dated 05 / 27 / 2025, pp. 107 / 149 104 / 125 flash chromatography (eluent: heptane / ethyl acetate) to obtain the title compound (69 mg, 63% yield) as a white solid. MS (ESI): 344 ([M+H]+) 3-[4-[5-(Difluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2oxazol-5-ol (Compound I-049)

[0227] To a solution of 4-acetylbenzonitrile (1.0 g, 6.88 mmol) in 30 ml of THF, sodium hydride (330 mg, 8.26 mmol, 60% in oil) was added in portions at 0 °C. The reaction was stirred for 30 min and ethyl trifluoroacetate (1.64 ml, 13.7 mmol) was then added. The mixture was stirred for 1 hour and then water was added. The mixture was extracted 3 times with ethyl acetate, washed with brine, dried over MgSCM and evaporated to obtain 4-(4,4,4-trifluoro-3-oxobutanoyl)benzonitrile (1.7 g, 91% yield) as a diketone and ketoenol mixture which was used in the next step without further purification.

[0228] Hydroxylamine hydrochloride (508 mg, 7.3 mmol) was added to a suspension of 4-(4,4,4-trifluoro-3-oxobutanoyl)benzonitrile (1.7 g, 7.0 mmol) in acetic acid (25 ml). The mixture was stirred at 50 °C for 2 hours. Hydroxylamine hydrochloride (100 mg) was then added and the mixture was stirred at 50 °C for a further 4 h. The reaction mixture was cooled to room temperature, poured into ice / water and stirred for 30 min. The precipitate was filtered, washed with water and dried under vacuum to obtain 4-{5-[trifluoromethyl]-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzonitrile (1.6 g, 85% yield) which was used in the next step without further purification.

[0229] For a mixture of 4-{5-[trifluoromethyl]-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzonitrile (550 mg, 2.14 mmol) and hydroxylamine hydrochloride (298 mg, 4.3 Petition 870250043647, dated 05 / 27 / 2025, pp. 108 / 149 A solution of 105 / 125 mmol) in methanol (10 ml) was added to sodium carbonate (455 mg, 4.3 mmol). The mixture was refluxed for 8 h. The solvent was then evaporated and the residue was dissolved in ethyl acetate, washed with water, dried over MgSCM and evaporated to obtain N'-hydroxy-4-[5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3yl]benzenecarboximidamide (396 mg, 54% yield, 85% purity) as a creamy solid which was used in the next step without further purification.

[0230] A mixture of N'-hydroxy-4-[5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]benzenecarboximidamide (250 mg, 0.86 mmol) in ethyl difluoroacetate (1.5 ml) was stirred overnight at 100 °C. The solvent was concentrated under reduced pressure and the residue was purified by preparative HPLC (eluent: acetonitrile / water (0.1% formic acid)) to obtain the title compound (110 mg, 36%) as a brown solid. MS (ESI): 350 ([M+H]+) 3-[4-(5-Methyl-1,3,4-oxadiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol (Compound I-053)

[0231] To a suspension of methyl 4-acetylbenzoate (15 g, 84.1 mmol) in 250 ml of diethyl ether, ethyl trifluoroacetate (13 g, 92.6 mmol) was added and a 0.5 M sodium methoxide solution in MeOH (202 ml, 101 mmol) was added dropwise. The mixture was stirred at room temperature for 24 hours and 1 M HCl (130 ml) was then added. The mixture was extracted 3 times with diethyl ether, dried over MgSO4 and evaporated to obtain methyl 4-(4,4,4-trifluoro-3-oxobutanoyl)benzoate (20.8 g, 74% yield, 82% purity) as a diketone and ketoenol mixture which was used in the next step without further purification. Petition 870250043647, dated 05 / 27 / 2025, pp. 109 / 149 106 / 125 MS (ESI): 275 ([M+H]+)

[0232] To a mixture of methyl 4-(4,4,4-trifluoro-3-oxobutanoyl)benzoate (8 g, 20.7 mmol) in acetic acid (50 ml) hydroxylamine hydrochloride (1.66 g, 23.8 mmol) was added. The mixture was stirred at 80 °C for 1.5 h. The reaction mixture was cooled to room temperature, poured into water (400 ml) and stirred for 15 min. The precipitate was filtered, washed with heptane and dried to obtain methyl 4-{5-trifluoromethyl-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzoate (6.2 g, 97% yield) as a beige solid. MS (ESI): 290 ([M+H]+)

[0233] To a mixture of methyl 4-{5-trifluoromethyl-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzoate (5.2 g, 17.8 mmol) in methanol (40 ml), water (5 ml) and sodium hydroxide (1.5 g, 35.7 mmol) were added. The mixture was stirred at 60 °C for 1.5 h. The mixture was poured into a cold mixture of 1M HCl (100 ml) and water (100 ml) and stirred for 5 min. The precipitate was filtered and dried to obtain 4-{5-trifluoromethyl-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzoic acid (3.8 g, 74% yield) as a beige solid. MS (ESI): 276 ([M+H]+)

[0234] To a mixture of 4-{5-trifluoromethyl-5-hydroxy-4,5-dihydro-1,2-oxazol-3-yl}benzoic acid (1.0 g, 3.63 mmol), acetohydrazide (151 mg, 2.03 mmol), 1-hydroxybenzotriazole (49 mg, 0.63 mmol) and EDCI (390 mg, 2.03 mmol) in DMF (7 ml) TEA (0.28 ml, 2.03 mmol) was added. The mixture was stirred overnight at room temperature and diluted with ethyl acetate. Water was then added. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC (eluent: acetonitrile / water (0.1% formic acid)) to obtain N'acetyl-4-[5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]benzohydrazide. Petition 870250043647, dated 05 / 27 / 2025, pp. 110 / 149 107 / 125 MS (ESI): 332 ([M+H]+)

[0235] A mixture of N'-acetyl-4-[5-hydroxy-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]benzohydrazide (313 mg, 0.94 mmol) in phosphorus oxychloride (2.6 mL, 28.3 mmol) was stirred at 60 °C in a microwave for 4 h, cooled to room temperature, and diluted with toluene. The solvent was then evaporated. The residue was diluted and the precipitate was purified by preparative HPLC (eluent: acetonitrile / water (0.1% formic acid)) to obtain the title compound (84 mg, 27% yield). MS (ESI): 314 ([M+H]+) 3-[4-(1,2-Thiazol-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-οχ3ζοΙ-5-οΙ (Compound I068)

[0236] 3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)4,5-dihydro-1,2-oxazol-5-ol (144 mg, 0.40 mmol), 4-bromoisothiazole (73 mg, 0.44 mmol), [1,1-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium (II) (13 mg, 0.02 mmol) and cesium carbonate (130 mg, 0.40 mmol) were dissolved in degassed dioxane (1.5 ml) and degassed water (0.5 ml). The mixture was stirred at 90 °C for 1 h and then cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in DCM, filtered over a silica gel cartridge, evaporated, and purified by preparative HPLC-MS (eluent: acetonitrile / water (0.1% formic acid)) to obtain the title compound (61 mg, 48% yield). MS (ESI): 315 ([M+H]+)

[0237] The compounds in Table 1 were prepared in analogy with the examples given above. Petition 870250043647, dated 05 / 27 / 2025, pp. 111 / 149 108 / 125 Table 1: Compounds according to formula (I) (I) Ex N° X R1 (F)m ( Het ) * ^(R2)n LogP Stereo 1.001 FH 1-(2-ethoxy-2-oxoethyl)-1H-pyrazol-4-yla 2.54^ I.002 FH 5-acetyl-2-thienyl 2.92M I 3.03 FH 3.25^. I.004 FH 1 -(4-fluorophenyl)-1 H-pyrazole-4-yla 3.531a! I.005 Cl H 1 -ethyl-1 H-pyrazole-4-yla 2.571a! I.006 FH 4 methyl-2-thienyl 3.74[a] I.007 FH 1 -(2-methylpropyl)-1 H-pyrazol-4-yla 3.061a] I.008 FH 4-phenyl-1,3-thiazol-2-yla 4.15Μ I.009 FH thiophene 3.31-3. 1.010 FH 1-methyl-1 H-pyrrole-3-yla 2.92^ 1.011 FH 1-(difluoromethyl)-1 H-pyrazole-4-yla 2.70^ 1.012 FH 1,3,5-trimethyl-1 H-pyrazol-4-yla 2.28^ 1-1-1-13-isopropyl. H-pyrazole-4-ila 2.771a! 1.014 FH 5-phenyl-2-thienyl 4.551a] 1.015 FH 5-formyl-2-thienyl 2.80[al 1.016 FH 1 -methyl-3-(trifluoromethyl)-1 H-pyrazol-4-ila 3.001a! 1.017 FH 3-F 1 -ethyl-1 H-pyrazole-4-yla 2.67[al 1.018 FH 5-(morpholin-4-ylmethyl)-2-thienyl 1.521a! 1.019 FH 3-methoxy-2-thienyl 3.371a! I.020 FH 5-isopropyl-1,3-thiazol-2-yl 3.691a! 1.021 FH furano-3-yl 2.92^ I.022 FH 2-F 1 methyl-1 H-pyrazol-4-ila 2.28^ I.023 Cl H 1,2-oxazole-4-ila 2.49^ I.024 FH - 1-benzyl-1 H-pyrazol-4-ila 3.13[a]. Petition 870250043647, of 27 / 05 / 2025, p. 112 / 149 109 / 125 Ex N° X R1 (F)m ( Het ) * ^(R2)n LogP Stereo 1.025 FH 1-(2-methoxy-ethyl)-1H-pyrazol-4-yla 2.26^ 1.026 F acetyl 1 -ethyl-1 H-pyrazol-4-yla 3.15^ 1 1027 FH isomero 1.025. -propyl-1 H-pyrazol-4-yla 2,751a] 1.028 FH 1-(carboxymethyl)-1H-pyrazol-4-yla 1.82^ 1.029 FH 5 methyl-2-furyl 3,441a] 1.030 Cl H 1 -methyl-1 H-pyrazol-2,213] 1.031 FH 1-(terc-butoxy-carbonyl)-1H-pyrazole-4-yla 3,151a] 1.032 FH 1,3-di methyl-1 H-pyrazol-4-yla 2.23^ I.033 FH 1-cyclo pentyl-1 H-pyrazole-4-2.23^ 1H. 0.931a for 1H-imidazole-1! I.035 FH 1 -phenyl-1 H-pyrazole-4-yla 3.471a! 1.036 FH 1 -(thiophene-2-ylmethyl)-1 H-pyrazole-4-yla 2.951a! I.037 FH 3-methyl-1,2-oxazole-5-yla 2.62^ I.038 FH 1-ethyl-1 H-triazol-4-yla 2.16^ I.039 FH 2-F 1,2-oxazole-4-yla 2.511a! 1.040 F 2-methoxyacetyl 1-ethyl-1 H-pyrazol-4-yl 3.06^ 1.041 F acetyl 1-ethyl-1 H-pyrazol-4-yl 3.151a! isomer 2 1.042 FH 2-F 1-ethyl-1 H-pyrazole-4-yla 2.62[al 1.043 FH 2-chloro-3-thienyl 3.711a! 1.044 FH 5-cyano-2-thienyl 3.13^ 1.045 FH 1-methyl-1 H-pyrrol-2-yla 3.07^ 1.046 FH 5-cyclo pentyl-1,2,4-oxadiazol-3-yla 3.91 M 1.047 FH 5-(2,4-difluorophenyl)-1,2,4-oxadiazol-3,81aa ! 1.048 FH 5-(2,4-difluorophenyl)-1,3,4-oxadiazol-2yla 3,191a! 1.049 FH 5-(difluoromethyl)-1,2,4-oxadiazol-3-yla 2.94[al I.050 FH 5-cyclo pentyl-1,3,4-oxadiazol-2-yla 3.071a! 1.051 FH 5 methyl-1,2,4-oxadiazol-3-yl 2,49[al 1.052 FH 5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl 3,401a! I.053 FH 5 methyl-1,3,4-oxadiazol-2-yl 2.01^ 1.054 FH 5-(difluoromethyl)-1,3,4-oxadiazol-2-yl 2.54[al I.055 FH 5-terc-butyl-1,3,4-thiazol-2-yl 3.026-yl FH 1 -tert-butyl-1 H-pyrazole-4-yla 3.061a! I.057 FH - 1-allyl-1H-imidazole-5-yl 1.29[a]. Petition 870250043647, of 27 / 05 / 2025, p. 113 / 149 110 / 125 Ex N° X R1 (F)m ( Het ) * ^(R2)n LogP Stereo 1.058 FH 5-(trifluoromethyl)-1,3,4-oxadiazol-2-yla 3.08^ 1.059 FH 5-(trifluoromethyl)-1,2,4-oxadiazol-3-yla 3.08^ FH. 1 -pyridin-2-yl-1 H-pyrazole-3-yla 3.501a] 1.061 FH 2-formyl-3-thienyl 2.781a] I.062 FH 5-formyl-3-thienyl 2.801a] I.063 FH 2-formyl-5-thienyl-3-3.063. FH 3-methyl-1,2,4-oxadiazol-5-yla 2,541a] I.065 FH 5-terc-butyl-1,3,4-oxadiazol-2-yla 2.90^ I.066 FH 1,3-thiazol-5-yla 2.31^ I.067 FH isothiazole-26-5-yla 2.541a] I.068 FH isothiazole-4-ila 2.551a! I.069 FH 5-cyclopropyl-1,3,4-oxadiazol-2-yla 2.46^ I.070 FH 1 -(cyclopropylmethyl)-l H-pyrazol-4-yla 2.861a! I.071 FH - 1-cyclopropyl-1H-pyrazole-4-yl 2.54[a]

[0238] The measurement of LogP values ​​was carried out in accordance with EEC directive 79 / 831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods: [a]The LogP value is determined by LC-UV measurement, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). [b]The LogP value is determined by LC-UV measurement, in a neutral range, with a 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). [c]The LogP value is determined by LC-UV measurement, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0239] If more than one LogP value is available in the same method, all values ​​are provided and separated by “+”. Petition 870250043647, dated 05 / 27 / 2025, pages 114 / 149 111 / 125

[0240] Calibration was performed with linear chain alkanes (with 3 to 16 carbon atoms) with known LogP values ​​(measurement of LogP values ​​using retention times with linear interpolation between successive alkanes). Lambda-max values ​​were determined using UV spectra from 200 nm to 400 nm and peak values ​​from chromatographic signals. NMR peak lists

[0241] The 1H-NMR data from selected examples are written in the form of lists of 1H-NMR peaks. For each signal peak, the δ-value is listed in ppm and the signal intensity is in parentheses. Between δ-value - signal intensity pairs, semicolons serve as delimiters.

[0242] The list of peaks in an example therefore has the form: δ1 (intensity1); δ2 (intensity2);........; δι (intensityi);......; δn (intensityn)

[0243] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the actual signal intensity relationships. From broad signals, multiple peaks or the middle of the signal and their relative intensity compared to the most intense signal in the spectrum can be shown.

[0244] To calibrate the chemical shift for 1H spectra, we use tetramethylsilane and / or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore, in NMR peak lists, the tetramethylsilane peak may occur, but not necessarily.

[0245] The 1H-NMR peak lists are similar to the classic 1H-NMR printouts and therefore generally contain all the peaks that are listed in the classic NMR interpretation. Petition 870250043647, dated 05 / 27 / 2025, pp. 115 / 149 112 / 125

[0246] In addition, they may show classic 1HNMR solvent imprinting signals, stereoisomers of the target compounds, which are also the subject of the invention, and / or impurity peaks.

[0247] To show compound signals in the delta range of solvents and / or water, the usual solvent peaks, for example, DMSO peaks in DMSO-D6 and the water peak are shown in our 1H-NMR peak lists and generally have average to high intensity.

[0248] The stereoisomer peaks of the target compounds and / or impurity peaks generally have, on average, a lower intensity than the peaks of the target compounds (e.g., with a purity > 90%).

[0249] These stereoisomers and / or impurities may be typical for the specific preparation process. Therefore, their peaks can help to recognize the reproduction of our preparation process through “byproduct fingerprints”.

[0250] A person skilled in the art, who calculates the peaks of the target compounds with known methods (MasterC, ACD simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed, optionally using additional intensity filters. This isolation would be similar to the relevant peak in the classical 1H-NMR interpretation.

[0251] Further details on the description of NMR data with peak lists can be found in the publication “Citation of NMR Peaklist Data within Patent Applications” from the Research Disclosure Database Number 564025._____________________ 1.002:1H-NMR (400.2 MHz, d6-DMSO): δ= 8.6983 (4.2); 7.9904 (2.9); 7.9806 (3.0); 7.9539 (1.8); 7.9081 (3.2); 7.8873 (4.8); 7.8132 (4.8); 7.7922 (3.7); 7.7870 (3.6); 7.7769 (2.7); 3.9992 (1.8); 3.9529 (2.3); 3.6132 (1.5); 3.5669 (1.2); 3.3300 (10.6); 2.8920 (9.8); 2.7329 (9.5); 2.5616 (16.0); 2.5074 (28.2); 2.5038 (33.5); 1.2378 (0.4); -0.0002 (2.0)________________ I.003: 1H-NMR (400.2 MHz, d6-DMSO): δ= = 8.6408 (3.3); 8.0426 (1.5); 8.0397 (1.6); 8.0360 (1.7); 8.0328 (1.6); 7.9530 (2.3); 7.8640 (2.7); 7.8430 (4.3); 7.7643 (4.3); 7.7432 (2.9); 7.6922 (1.0); 7.6850 (1.0); 7.6797 (2.0); 7.6725 (1.9); 7.6560 (2.0); 7.6530 (2.1); 7.6434 (1.0); 7.6404 (1.0); 3.9838 (1.5); 3.9376 (1.9); 3.6044 (1.2); 3.5582 (0.9); 3.3300 (20.0); 2.8909 (16.0); 2.7318 (14.2); 2.5247 (0.5); 2.5113 (10.6); 2.5071 (21.5); 2.5026 (28.2); 2.4981 (20.2); 2.4937 (9.7); -0.0002 (2.2) Petition 870250043647, dated 05 / 27 / 2025, pp. 116 / 149 113 / 125 1.004:1H-NMR (300.2 MHz, d6-DMSO): δ= 9.1343 (0.5); 8.3485 (0.5); 7.8486 (0.6); 7.7954 (0.6); 7.4222 (0.4); 3.3477 (16.0); 2.5337 (1.7); 2.5278 (3.5); 2.5218 (4.8); 2.5157 (3.5); 2.5098 (1.6); 0.0198 (5.1)____________________________________________________ 1.005:1H-NMR (300.2 MHz, d6-DMSO): δ= 8.6389 (0.4); 8.3337 (0.4); 7.9884 (0.5); 7.7096 (2.0); 5.7795 (0.6); 4.1899 (0.4); 4.1566 (0.4); 3.3469 (16.0); 2.5343 (1.4); 2.5285 (2.9); 2.5224 (4.0); 2.5163 (2.9); 2.5104 (1.4); 1.4551 (0.4); 1.4309 (1.0); 1.4067 (0.4); 0.0207 (4.7)_________________________________________________________________________________________ 1.006:1H-NMR (400.2 MHz, d6-DMSO): δ= 8.6497 (4.2); 7.7555 (0.6); 7.7473 (0.4); 7.7321 (16.0); 7.7166 (0.4); 7.7084 (0.6); 7.4827 (3.3); 7.4800 (3.4); 7.2031 (3.3); 3.9709 (1.8); 3.9247 (2.3); 3.5870 (1.4); 3.5404 (1.1); 3.3316 (14.6); 2.8912 (1.2); 2.7322 (1.1); 2.5254 (0.5); 2.5120 (9.2); 2.5077 (18.4); 2.5031 (24.0); 2.4986 (17.1); 2.4941 (8.2); 2.2514 (11.2); 2.2500 (11.2); 1.2370 (0.4); -0.0002 (2.2)________________________________________________________________ 1.007:1H-NMR (300.2 MHz, d6-DMSO): δ= 8.6290 (0.6); 8.3062 (1.2); 8.0004 (1.3); 7.7117 (6.0); 3.9857 (0.5); 3.9669 (1.1); 3.9429 (1.1); 3.9243 (0.6); 3.6047 (0.4); 3.3471 (16.0); 2.5279 (3.9); 2.5219 (5.2); 2.5159 (3.8); 0.8981 (4.0); 0.8758 (3.9); 0.0200 (5.2)________________________________________________________________________________________________________________________________ 1.008:1H-NMR (400.1 MHz, d6-DMSO): δ= 8.7200 (0.8); 8.2670 (4.4); 8.1624 (3.6); 8.1434 (4.2); 8.0919 (3.8); 8.0727 (4.0); 7.9613 (3.7); 7.9027 (4.1); 7.8832 (3.6); 7.5225 (1.8); 7.5039 (3.8); 7.4856 (2.4); 7.4224 (1.4); 7.4052 (1.8); 7.3857 (0.7); 4.0384 (1.6); 3.9918 (2.0); 3.6454 (1.8); 3.5989 (1.4); 3.3186 (97.0); 2.9000 (16.0); 2.7410 (15.2); 2.5106 (14.9) 1.009:1H-NMR (400.2 MHz, d6-DMSO): δ = 8.6593 (5.1); 7.9527 (0.4); 7.7929 (2.5); 7.7871 (1.2); 7.7710 (16.0); 7.7617 (15.4); 7.7456 (1.3); 7.7396 (2.6); 7.6641 (3.7); 7.6614 (4.5); 7.6550 (4.1); 7.6523 (4.5); 7.6402 (4.6); 7.6376 (4.0); 7.6276 (4.9); 7.6250 (4.0); 7.1933 (4.2); 7.1842 (4.2); 7.1807 (4.1); 7.1715 (3.9); 3.9791 (3.6); 3.9329 (4.5); 3.5947 (2.6); 3.5482 (2.1); 3.3271 (28.5); 2.8912 (2.8); 2.7326 (2.4); 2.7317 (2.3); 2.6715 (0.4); 2.5250 (1.2); 2.5200 (2.0); 2.5116 (27.4); 2.5071 (55.5); 2.5026 (72.3); 2.4980 (50.8); 2.4935 (23.7); 2.3294 (0.4); 1.2393 (0.7); -0.0002 (6.4) 1.010:1H-NMR (400.1 MHz, CDCl 3 ): δ= 8.0152 (0.5); 7.6143 (1.6); 7.5932 (3.1); 7.5454 (3.0); 7.5239 (1.7); 7.5175 (0.7); 7.2585 (85.0); 6.9914 (1.0); 6.9865 (1.6); 6.9819 (1.0); 6.6555 (0.8); 6.6495 (1.4); 6.6437 (1.0); 6.4760 (1.0); 6.4712 (1.2); 6.4645 (1.0); 4.0869 (0.4); 3.7480 (1.0); 3.7202 (0.3); 3.7041 (10.7); 3.5491 (1.0); 3.5070 (0.8); 3.3613 (0.6); 3.1011 (0.4); 3.0701 (0.3); 2.9536 (3.8); 2.8810 (3.4); 1.5334 (32.8); 1.4308 (0.4); 1.4043 (0.6); 1.3701 (0.9); 1.3325 (1.2); 1.2842 (3.0); 1.2567 (16.0); 1.1591 (0.7); 1.0785 (0.6); 0.9387 (0.5); 0.8954 (1.5); 0.8806 (3.1); 0.8630 (2.2); 0.8537 (2.4); 0.8360 (2.0); 0.1460 (0.5); 0.0079 (5.3); -0.0002 (105.3); -0.0082 (5.3); -0.1498 (0.5) 1.011:1H-NMR (499.9 MHz, d6-DMSO): δ= 8.8512 (15.7); 8.6399 (9.8); 8.3782 (15.4); 7.9755 (3.2); 7.8570 (7.8); 7.8468 (10.4); 7.8301 (16.0); 7.7675 (15.3); 7.7507 (10.7); 7.7386 (3.9); 3.9754 (6.0); 3.9384 (7.3); 3.6032 (5.0); 3.5661 (4.2); 3.3301 (5.0); 2.5082 (4.6); 2.5051 (6.2); 2.5018 (5.1); -0.0002 (2.4)________________________________________________ 1.012:1H-NMR (300.2 MHz, d6-DMSO): δ= 8.6505 (0.5); 7.7822 (0.8); 7.7541 (0.9); 7.4003 (0.9); 7.3722 (0.8); 3.9420 (0.4); 3.7288 (2.8); 3.3481 (16.0); 2.5340 (1.6); 2.5280 (3.4); 2.5219 (4.7); 2.5159 (3.3); 2.5100 (1.5); 2.2615 (3.3); 2.1679 (3.2); 2.0094 (0.3); 0.0201 (5.4)________________________________________________________________________________________________ 1.013:1H-NMR (300.2 MHz, d6-DMSO): δ= 8,7270 (0,6); 7,8766 (1,6); 7,8485 (1,9); 7,5812 (2,2); 7,5769 (2,0); 7,5710 (1,5); 7,5532 (1,6); 6,4022 (1,8); 6,3962 (1,8); 4,5829 (0,4); 4,5610 (0,5); 4,5392 (0,4); 4,0376 (0,9); 3,9760 (0,9); 3,6482 (0,6); 3,5851 (0,4); 3,3454 (16,0); 2,5340 (1,9); 2,5280 (4,0); 2,5220 (5,4); 2,5159 (3,9); 2,5100 (1,8); 2,0092 (0,9); 1,4119 (3,8); 1,4085 (3,8); 1,3902 (3,8); 1,3868 (3,7); 1,1946 (0,5); 0,0200 (8,1)_____________________________________ I.014: 1H-NMR (400,1 MHz, d6-DMSO): δ= 8.6578 (1.7); 7.9520 (2.0); 7.8267 (5.1); 7.8051 (14.7); 7.7820 (14.2); 7.7604 (5.1); 7.7322 (5.9); 7.7291 (7.7); 7.7110 (8.6); 7.6975 (7.0); 7.6878 (8.1); 7.5988 (8.1); 7.5892 (6.9); 7.4718 (4.3); 7.4533 (8.8); 7.4337 (5.4); 7.3648 (3.2); 7.3464 (4.5); 7.3279 (1.7); 3.9821 (4.0); 3.9360 (5.0); 3.6019 (3.3); 3.5557 (2.6); 3.3039 (108.0); 2.8901 (16.0); 2.7481 (0.4); 2.7315 (12.8); 2.5091 (12.4); 2.5048 (23.4); 2.5004 (30.4); 2.4960 (21.8); 1.2329 (0.6); 0.0078 (1.9); -0.0002 (34.8); -0.0083 (1.4) Petition 870250043647, dated 05 / 27 / 2025, pp. 117 / 149 114 / 125 1.015:1H-NMR (400.2 MHz, d6-DMSO): δ= 9.9407 (16.0); 8.7090 (6.2); 8.0872 (6.2); 8.0772 (6.7); 7.9541 (1.9); 7.9446 (6.3); 7.9233 (9.4); 7.8823 (6.3); 7.8724 (5.9); 7.8328 (8.9); 7.8114 (6.4); 7.6927 (0.9); 7.6782 (0.9); 4.0067 (3.2); 3.9728 (0.3); 3.9604 (4.1); 3.6210 (2.4); 3.5741 (2.1); 3.3308 (18.9); 2.8924 (12.2); 2.7338 (10.2); 2.7329 (10.5); 2.5266 (0.9); 2.5219 (1.3); 2.5132 (18.5); 2.5088 (38.5); 2.5042 (50.9); 2.4996 (36.5); 2.4951 (17.5); 1.2374 (0.4); -0.0002 (5.1)________________________________________________________________________________________________________________________________ 1.016:1H-NMR (300.2 MHz, d6-DMSO): δ= 8.6885 (3.7); 8.2877 (4.1); 8.2854 (4.0); 7.8226 (5.2); 7.7944 (6.3); 7.5425 (5.3); 7.5149 (4.4); 4.0840 (0.3); 4.0602 (1.0); 4.0365 (1.0); 4.0122 (2.8); 3.9906 (15.3); 3.9503 (3.1); 3.6281 (1.8); 3.5663 (1.4); 3.3527 (16.0); 2.5340 (2.0); 2.5281 (4.2); 2.5221 (5.6); 2.5160 (4.0); 2.5102 (1.8); 2.0127 (1.2); 2.0085 (4.1); 1.2175 (1.1); 1.1938 (2.2); 1.1701 (1.1); 0.0183 (6.4)________________________________________________________________ 1.017:1H-NMR (300.2 MHz, d6-DMSO): δ= 8.7104 (2.1); 8.3085 (1.1); 8.3022 (1.2); 8.0112 (1.4); 7.8963 (0.6); 7.8696 (1.1); 7.8413 (0.6); 7.6434 (0.7); 7.6381 (0.8); 7.6028 (1.8); 7.5808 (0.9); 7.5752 (0.6); 4.2573 (0.6); 4.2331 (1.8); 4.2089 (1.9); 4.1847 (0.6); 4.0062 (0.8); 3.9441 (1.1); 3.6252 (0.6); 3.5637 (0.5); 3.3616 (16.0); 2.5344 (3.3); 2.5284 (6.8); 2.5224 (9.4); 2.5163 (6.8); 2.5104 (3.3); 1.4546 (2.2); 1.4304 (4.9); 1.4061 (2.1); 0.0312 (0.4); 0.0203 (11.0); 0.0094 (0.5)________________________________________________________________________________________________________________ 1.018:1H-NMR (400.1 MHz, d6-DMSO): δ= 8.6246 (3.8); 7.7307 (16.0); 7.4930 (1.6); 7.4840 (1.7); 7.0182 (1.3); 7.0095 (1.2); 3.9672 (1.3); 3.9211 (1.7); 3.6913 (3.6); 3.6016 (2.6); 3.5901 (3.8); 3.5809 (3.4); 3.5363 (0.9); 3.3043 (58.7); 2.8902 (1.1); 2.7313 (0.9); 2.5046 (9.6); 2.5002 (12.7); 2.4958 (9.3); 2.4331 (2.7); -0.0002 (5.7)_________________________________ 1.019:1H-NMR (400,1 MHz, d6-DMSO): δ= 8,6109 (3,9); 7,9519 (0,6); 7,7854 (2,4); 7,7638 (5,0); 7,7230 (4,8); 7,7014 (2,3); 7,5731 (2,8); 7,5592 (3,0); 7,1814 (3,1); 7,1675 (2,9); 3,9348 (16,0); 3,8958 (1,9); 3,5683 (1,2); 3,5221 (1,0); 3,3037 (55,5); 2,8901 (4,0); 2,7310 (3,3); 2,5088 (4,5); 2,5046 (8,8); 2,5001 (11,6); 2,4957 (8,5); 0,0079 (0,4); -0,0002 (8,2); -0,0083 (0,4)____________________________________________________________________________________________________ 1.020:1H-NMR (400,1 MHz, d6-DMSO): δ= 8,6875 (3,6); 8,0056 (4,1); 7,9862 (5,2); 7,8425 (5,1); 7,8225 (4,1); 7,7229 (4,9); 4,0073 (2,0); 3,9609 (2,6); 3,6138 (2,2); 3,5675 (1,7); 3,3184 (114,8); 3,2833 (1,6); 3,2667 (0,7); 2,8994 (0,9); 2,7406 (0,9); 2,6201 (0,4); 2,5105 (15,6); 1,3544 (16,0); 1,3376 (15,6)___________________________________________________ 1.021:1H-NMR (400,2 MHz, d6-DMSO): δ = 8,6294 (3,7); 8,3198 (2,6); 7,9537 (1,4); 7,7849 (1,8); 7,7807 (2,8); 7,7767 (1,7); 7,7581 (0,5); 7,7556 (0,6); 7,7356 (16,0); 7,7129 (0,3); 7,0504 (2,2); 7,0477 (2,2); 3,9724 (1,5); 3,9261 (1,9); 3,5961 (1,2); 3,5490 (0,9); 3,3319 (11,3); 2,8915 (9,1); 2,7325 (8,1); 2,5119 (10,7); 2,5078 (19,0); 2,5034 (23,7); 2,4989 (17,1); -0,0002 (1,8)_____________________________________________________________________________________________________ I.022:1H-NMR (400,1 MHz, CDCI3): δ = 8,0700 (1,9); 7,8475 (1,4); 7,8275 (2,7); 7,8076 (1,6); 7,7827 (5,0); 7,7506 (4,9); 7,4142 (10,5); 7,3257 (2,2); 7,3054 (2,0); 7,2602 (2,0); 7,2288 (2,0); 3,9642 (16,0); 3,7518 (1,3); 3,7052 (2,1); 3,5663 (1,8); 3,5218 (1,1); 2,9657 (0,5); 2,8766 (0,5); 2,6050 (5,5); 1,2572 (4,8); 0,8786 (0,9); 0,8534 (0,8); -0,0002 (10,8) 1.023:1H-NMR (400,1 MHz, CDCI3): δ = 8.7504 (16.0); 8.5964 (16.0); 8.0093 (0.6); 7.7370 (9.3); 7.7160 (11.9); 7.5650 (12.1); 7.5439 (9.3); 7.2589 (44.4); 3.8141 (4.6); 3.7694 (6.6); 3.6222 (2.3); 3.5719 (4.6); 3.5272 (3.2); 2.9546 (4.0); 2.8784 (3.6); 1.5979 (0.4); 1.5491 (12.6); 1.3701 (0.4); 1.3318 (0.6); 1.2842 (1.5); 1.2567 (8.4); 1.0891 (0.3); 0.8969 (0.8); 0.8807 (1.7); 0.8628 (1.1); 0.8540 (1.1); 0.8363 (1.0); 0.8137 (0.6); 0.0078 (2.5); -0.0002 (53.4) 1.024:1H-NMR (499.9 MHz, d6-DMSO): δ = 8.6526 (2.3); 8.4647 (3.1); 8.0777 (3.2); 7.7517 (16.0); 7.4304 (0.8); 7.4276 (0.4); 7.4166 (2.3); 7.4016 (2.1); 7.3720 (0.9); 7.3696 (0.8); 7.3576 (1.3); 7.3509 (2.4); 7.3480 (2.5); 7.3434 (1.0); 7.3343 (1.7); 5.4149 (5.0); 4.0048 (1.3); 3.9679 (1.5); 3.6288 (0.9); 3.5917 (0.8); 3.3764 (1.8); 2.5643 (0.8); 2.5610 (1.7); 2.5574 (2.4); 2.5538 (1.8); 2.5504 (0.9)________________________________________________________________________________ 1.025:1H-NMR (300.2 MHz, d6-DMSO): δ = 8.6223 (1.0); 8.2944 (0.8); 8.0096 (0.9); 7.7133 (4.1); 4.3194 (0.4); 4.3021 (0.7); 4.2840 (0.4); 3.9273 (0.4); 3.7568 (0.4); 3.7389 (0.7); 3.7215 (0.4); 3.3459 (16.0); 3.2642 (4.0); 2.5336 (1.9); 2.5279 (3.8); 2.5219 (5.2); 2.5159 (3.8); 2.5103 (1.8); 0.0203 (4.6)__________________________________________________________________ I.026: 1H-NMR (499.9 MHz, d6-DMSO): δ = 8.3227 (4.5); 7.9779 (4.6); 7.7235 (2.0); 7.7065 (6.1); 7.6884 (6.0); 7.6714 (2.2); 4.2916 (1.0); 4.2532 (1.6); 4.1856 (1.2); 4.1710 (3.7); 4.1561 (5.3); 4.1419 (1.3); 4.1161 (1.5); 3.3183 (9.9); 2.5077 (3.2); 2.5043 (4.2); 2.5009 (3.2); 2.1526 (16.0); 1.4330 (4.2); 1.4184 (8.7); 1.4038 (4.1) Petition 870250043647, dated 05 / 27 / 2025, pp. 118 / 149 115 / 125 1.027:1H-NMR (300.2 MHz, d6-DMSO): δ = 8.6243 (0.5); 8.3223 (0.7); 7.9943 (0.7); 7.7102 (3.6); 4.1258 (0.3); 4.1027 (0.7); 4.0796 (0.3); 3.9240 (0.4); 3.3452 (16.0); 2.5336 (1.7); 2.5279 (3.4); 2.5219 (4.6); 2.5159 (3.3); 2.5102 (1.6); 1.8545 (0.4); 1.8308 (0.4); 0.9001 (0.7); 0.8756 (1.4); 0.8509 (0.6); 0.0203 (4.1)____________________________________________________ 1.028:1H-NMR (499.9 MHz, d6-DMSO): δ = 8.6583 (1.0); 8.3355 (5.7); 8.0707 (5.9); 7.7824 (1.0); 7.7808 (0.9); 7.7770 (0.8); 7.7645 (12.6); 7.7616 (13.2); 7.7493 (0.7); 7.7437 (1.1); 5.0477 (10.3); 4.0163 (2.2); 3.9795 (2.7); 3.6389 (1.7); 3.6019 (1.4); 3.3840 (1.3); 2.5680 (1.5); 2.5645 (3.2); 2.5609 (4.4); 2.5573 (3.3); 2.5539 (1.7); 1.9689 (16.0); -0.0002 (0.8)__________________________________________________________________________________________________________________ 1.029:1H-NMR (400.2 MHz, d6-DMSO): δ = 8.6254 (3.2); 7.9532 (2.5); 7.7336 (15.2); 6.9859 (1.8); 6.9778 (1.8); 6.2556 (1.3); 6.2498 (1.3); 3.9658 (1.2); 3.9196 (1.5); 3.5796 (1.0); 3.5337 (0.8); 3.3286 (13.1); 2.8913 (16.0); 2.7321 (14.5); 2.5111 (9.4); 2.5072 (18.4); 2.5028 (23.9); 2.4983 (17.5); 2.4665 (0.5); 2.3615 (8.2); -0.0002 (1.8)_____________ 1.030:1H-NMR (400.1 MHz, CDCl 3 ): δ = 7.8624 (3.4); 7.7928 (4.4); 7.6952 (4.5); 7.6545 (3.4); 7.6337 (5.0); 7.5292 (4.8); 7.5083 (3.7); 7.3282 (14.5); 7.3180 (3.0); 3.9620 (16.0); 3.9525 (3.7); 3.7448 (1.8); 3.7003 (2.6); 3.5195 (1.9); 3.4750 (1.3); 2.5801 (0.6); 2.5759 (0.5); 2.2751 (11.9); 1.2860 (0.9); 1.2566 (4.6); 0.8804 (0.9); 0.8534 (0.8); 0.8366 (0.7); -0.0002 (16.5); -0.0094 (3.6)_________________________________________________________________________ 1.031:1H-NMR (300.2 MHz, d6-DMSO): δ = 8.8900 (0.9); 8.6608 (1.0); 8.4199 (0.9); 7.9296 (0.6); 7.9013 (0.9); 7.7819 (0.9); 7.7537 (0.6); 3.9533 (0.4); 3.3447 (16.0); 2.5342 (1.6); 2.5282 (3.4); 2.5222 (4.7); 2.5161 (3.4); 2.5102 (1.6); 1.6322 (8.7); 0.0203 (5.6)________________________________________________________________________________________________________________ 1.032:1H-NMR (300.2 MHz, d6-DMSO): δ = 8.0383 (0.8); 7.7503 (0.6); 7.7221 (0.8); 7.5696 (0.8); 7.5414 (0.6); 3.9221 (0.4); 3.8130 (2.5); 3.3462 (16.0); 2.5338 (2.0); 2.5278 (4.1); 2.5218 (5.6); 2.5158 (4.1); 2.5099 (1.9); 2.3473 (2.7); 0.0201 (5.9) 1.033:1H-NMR (300.2 MHz, d6-DMSO): δ = 8.6213 (1.3); 8.3662 (2.9); 7.9880 (3.0); 7.7466 (0.4); 7.7159 (9.8); 7.6843 (0.4); 4.7491 (0.6); 4.7250 (0.9); 4.7033 (0.6); 3.9855 (1.0); 3.9240 (1.4); 3.6060 (0.9); 3.5432 (0.7); 3.3464 (16.0); 2.5337 (2.3); 2.5279 (4.6); 2.5219 (6.2); 2.5159 (4.5); 2.5101 (2.1); 2.1541 (0.4); 2.1360 (0.7); 2.1103 (0.9); 2.0924 (0.7); 2.0710 (0.4); 2.0088 (0.9); 1.9868 (0.9); 1.9680 (0.7); 1.9420 (0.5); 1.8543 (0.6); 1.8411 (0.8); 1.8278 (0.9); 1.8044 (0.7); 1.6990 (0.7); 1.6888 (0.6); 1.6848 (0.8); 1.6780 (0.9); 1.6599 (0.7); 1.6500 (0.5); 0.0198 (5.0) 1.034:1H-NMR (300.2 MHz, d6-DMSO): δ = 9.4933 (2.0); 8.8031 (0.4); 8.2948 (1.9); 8.2896 (2.7); 8.2841 (1.6); 7.9963 (0.9); 7.9869 (0.5); 7.9656 (8.0); 7.9569 (8.0); 7.9355 (0.6); 7.9260 (1.0); 7.7882 (2.4); 4.0634 (1.6); 4.0014 (2.1); 3.6990 (1.3); 3.6365 (1.0); 2.9892 (0.3); 2.5340 (2.3); 2.5280 (5.2); 2.5220 (7.3); 2.5159 (5.4); 2.5100 (2.7); 1.9285 (16.0); 1.3886 (0.3); 0.0188 (8.7); 0.0079 (0.4)________________________________________________________________________________ I.035:1H-NMR (300.2 MHz, CDCl3): δ = 8.2691 (2.0); 8.0854 (1.9); 7.7943 (1.3); 7.7685 (1.6); 7.7574 (1.3); 7.7289 (2.4); 7.6826 (2.4); 7.6540 (1.1); 7.5604 (0.8); 7.5356 (1.4); 7.5080 (0.9); 7.4012 (0.5); 7.3766 (0.8); 7.3518 (0.3); 7.2984 (26.3); 3.8226 (0.7); 3.7634 (1.2); 3.6204 (0.8); 3.5628 (0.5); 3.4509 (1.4); 1.5843 (16.0); 0.1074 (0.3); 0.0486 (1.6); 0.0379 (33.9); 0.0271 (1.5)________________________________________________________________________________________________ 1.036:1H-NMR (400,1 MHz, d6-DMSO): δ = 8,5830 (1,1); 8,3682 (3,1); 8,0174 (3,2); 7,7124 (0,5); 7,7070 (0,4); 7,6887 (16,0); 7,6751 (1,6); 7,6530 (0,4); 7,4904 (1,3); 7,4874 (1,4); 7,4777 (1,4); 7,4747 (1,4); 7,1493 (1,2); 7,1429 (1,3); 7,0195 (1,3); 7,0108 (1,3); 7,0069 (1,3); 6,9982 (1,1); 5,5461 (5,2); 3,9667 (0,4); 3,9475 (1,2); 3,9201 (0,4); 3,9014 (1,5); 3,5703 (1,2); 3,5241 (1,0); 3,3038 (50,0); 2,9466 (0,4); 2,8899 (1,3); 2,7309 (1,1); 2,5085 (5,0); 2,5044 (9,6); 2,4999 (12,7); 2,4955 (9,3); 0,0078 (0,4); -0,0002 (7,8)________________________________________________________________ I.037:1H-NMR (300,2 MHz, d6-DMSO): δ = 8,7470 (3,3); 7,9774 (4,2); 7,9492 (8,5); 7,8977 (8,4); 7,8696 (4,0); 7,0401 (8,0); 4,0434 (2,6); 3,9814 (3,4); 3,6498 (2,4); 3,5877 (1,8); 3,3532 (16,0); 2,5270 (7,1); 2,5216 (8,7); 2,5161 (6,5); 2,3234 (20,6); 0,0179 (7,7)______________________________________________________________________________________________________ I. 038: 1H-NMR (499.9 MHz, d6-DMSO): δ = 8.7109 (10.4); 8.6588 (2.9); 7.9713 (6.5); 7.9545 (8.4); 7.8188 (8.1); 7.8020 (6.8); 4.4712 (2.2); 4.4566 (6.8); 4.4419 (6.9); 4.4272 (2.2); 3.9849 (3.3); 3.9480 (4.0); 3.6105 (2.5); 3.5734 (2.1); 3.3559 (1.5); 2.5079 (0.8); 2.5043 (1.1); 2.5008 (0.8); 1.5135 (7.6); 1.4988 (16.0); 1.4842 (7.7) Petition 870250043647, dated 05 / 27 / 2025, pp. 119 / 149 116 / 125 1.039:1H-NMR (400.1 MHz, d6-DMSO): δ = 9.6242 (14.8); 9.2888 (13.7); 9.2856 (11.9); 9.2799 (6.8); 8.7734 (0.5); 8.6936 (11.5); 8.3035 (0.7); 7.9519 (2.4); 7.9038 (0.4); 7.8632 (5.7); 7.8431 (12.4); 7.8237 (13.6); 7.7945 (7.4); 7.6959 (9.4); 7.6754 (7.3); 6.4881 (0.7); 4.0118 (0.4); 3.9957 (0.4); 3.9647 (4.1); 3.9174 (5.2); 3.6041 (7.0); 3.5575 (5.5); 3.5108 (0.4); 3.3918 (0.4); 3.3009 (227.5); 2.8921 (16.0); 2.7335 (13.8); 2.7119 (0.4); 2.6960 (0.4); 2.6743 (0.4); 2.6704 (0.6); 2.5677 (0.7); 2.5099 (29.8); 2.5056 (57.0); 2.5011 (75.0); 2.4966 (53.7); 2.3278 (0.4); 1.3359 (0.4); 1.2981 (0.7); 1.2604 (1.3); 1.2406 (4.5); 1.1770 (0.4); 0.8698 (0.5); 0.8540 (1.1); 0.8379 (0.6); 0.8075 (0.4); -0.0002 (40.8)_________________________________________________________________________________________ 1.040:1H-NMR (300.2 MHz, CDCl 3 ): δ = 7.8480 (3.2); 7.8462 (3.3); 7.7433 (3.4); 7.6934 (2.5); 7.6649 (4.0); 7.5731 (4.0); 7.5445 (2.5); 7.2987 (1.1); 4.2897 (1.0); 4.2653 (3.2); 4.2407 (3.9); 4.2166 (1.1); 4.1826 (3.9); 4.1559 (3.9); 4.0986 (0.8); 4.0468 (0.7); 4.0430 (0.7); 3.9858 (1.2); 3.9820 (1.3); 3.8410 (2.2); 3.7801 (1.2); 3.4810 (16.0); 1.5961 (3.5); 1.5717 (7.3); 1.5473 (3.4); 1.2889 (0.4); 0.1199 (1.2); 0.1080 (24.6); 0.0972 (1.1); 0.0958 (1.2); 0.0327 (1.1) 1.041:1H-NMR (499.9 MHz, d6-DMSO): δ = 8.3229 (4.5); 7.9781 (4.6); 7.7238 (2.0); 7.7068 (6.1); 7.6887 (6.0); 7.6716 (2.2); 4.2916 (0.9); 4.2533 (1.6); 4.1859 (1.2); 4.1714 (3.7); 4.1564 (5.1); 4.1422 (1.4); 4.1164 (1.5); 3.3182 (9.2); 2.5081 (3.0); 2.5046 (4.2); 2.5012 (3.2); 2.1529 (16.0); 1.4333 (4.1); 1.4187 (8.7); 1.4042 (4.2)____________________________________ 1.042:1H-NMR (300.2 MHz, d6-DMSO): δ = 8.6843 (0.7); 8.4088 (0.8); 8.0554 (0.8); 7.7619 (0.4); 7.5751 (0.4); 4.1896 (0.7); 4.1653 (0.7); 3.3475 (16.0); 2.5345 (1.6); 2.5286 (3.2); 2.5226 (4.4); 2.5165 (3.3); 2.5107 (1.6); 1.4551 (0.8); 1.4309 (1.7); 1.4066 (0.8); 0.0208 (4.9)_________________________________________________________________________________________ 1.043:1H-NMR (400.2 MHz, d6-DMSO): δ = 8.6801 (8.8); 7.9535 (2.6); 7.8325 (6.1); 7.8115 (9.2); 7.7303 (9.3); 7.7093 (6.2); 7.6111 (6.0); 7.5967 (6.5); 7.3186 (6.4); 7.3041 (5.9); 3.9989 (3.4); 3.9526 (4.2); 3.6172 (2.6); 3.5707 (2.1); 3.3291 (23.3); 2.8914 (16.0); 2.7324 (14.8); 2.5074 (37.4); 2.5031 (46.2); 2.4987 (33.2); 1.2395 (0.4); -0.0002 (3.2)______________ 1.044:1H-NMR (400.2 MHz, d6-DMSO): δ = 8.7075 (11.8); 8.0430 (9.2); 8.0331 (9.8); 7.9028 (7.6); 7.8815 (14.1); 7.8318 (16.0); 7.8241 (10.0); 7.8102 (7.7); 4.0043 (4.6); 3.9579 (5.8); 3.6186 (3.4); 3.5720 (2.8); 3.3297 (25.3); 2.8922 (1.7); 2.7336 (1.4); 2.7327 (1.4); 2.6726 (0.4); 2.5263 (1.3); 2.5215 (2.0); 2.5129 (27.3); 2.5084 (55.6); 2.5039 (72.8); 2.4993 (51.9); 2.4948 (24.9); 2.3307 (0.4); 1.2375 (0.9); -0.0002 (6.8)_________________________________________ 1.045:1H-NMR (400.1 MHz, CDCl 3 ): δ = 8.0010 (0.8); 7.6969 (3.4); 7.6760 (4.0); 7.4862 (4.1); 7.4652 (3.2); 7.2579 (11.2); 6.7614 (1.5); 6.7562 (2.1); 6.7507 (1.4); 6.3244 (1.4); 6.3199 (1.5); 6.3153 (1.8); 6.3110 (1.6); 6.2289 (1.6); 6.2219 (2.0); 6.2132 (1.3); 3.7583 (1.7); 3.7137 (3.5); 3.7053 (16.0); 3.5664 (1.6); 3.5220 (1.0); 2.9523 (5.1); 2.8739 (4.8); 1.5624 (1.7); 1.2852 (0.5); 1.2574 (2.7); 0.8808 (0.5); 0.8634 (0.4); 0.8539 (0.4); 0.8370 (0.4); -0.0002 (13.9) 1.046:1H-NMR (300.2 MHz, CDCl3): δ = 8.2068 (3.2); 8.2006 (1.1); 8.1842 (1.2); 8.1781 (3.6); 7.8214 (3.7); 7.8152 (1.2); 7.7987 (1.1); 7.7927 (3.1); 7.2988 (12.4); 3.8264 (1.2); 3.7671 (2.1); 3.6689 (2.6); 3.6245 (1.3); 3.5620 (0.7); 3.4838 (0.8); 3.4570 (1.3); 3.4306 (0.9); 2.2606 (0.5); 2.2447 (0.8); 2.2397 (0.6); 2.2173 (1.0); 2.2061 (0.7); 2.2012 (0.6); 2.1783 (0.4); 2.0884 (0.8); 2.0704 (0.7); 2.0631 (1.0); 2.0446 (0.7); 2.0374 (0.6); 2.0221 (0.6); 1.9991 (0.3); 1.9506 (0.4); 1.9425 (0.6); 1.9320 (0.7); 1.9142 (0.9); 1.8933 (0.7); 1.8836 (0.4); 1.8624 (0.4); 1.8410 (0.5); 1.8086 (0.9); 1.7962 (0.7); 1.7862 (0.9); 1.7695 (0.6); 1.7593 (0.4); 1.6116 (16.0); 0.0482 (0.7); 0.0375 (18.0); 0.0267 (0.6)________________________________________________________________________________ 1.047:1H-NMR (300.2 MHz, d6-DMSO): δ = 8,9745 (0,3); 8,9048 (0,4); 8,3833 (1,1); 8,3612 (1,5); 8,3546 (2,0); 8,3337 (2,0); 8,3047 (1,2); 8,2525 (0,3); 8,2147 (5,5); 8,1865 (7,0); 7,9792 (6,8); 7,9512 (5,4); 7,7314 (1,2); 7,7236 (1,3); 7,6933 (2,1); 7,6638 (1,2); 7,6552 (1,3); 7,4738 (1,1); 7,4686 (1,1); 7,4469 (2,0); 7,4175 (1,1); 7,4119 (1,0); 4,0437 (1,9); 3,9814 (2,4); 3,6550 (2,3); 3,6218 (0,5); 3,5930 (1,8); 3,3438 (16,0); 3,2129 (0,5); 3,1832 (0,5); 3,1545 (0,5); 2,7491 (0,4); 2,5890 (0,4); 2,5285 (34,7); 2,5226 (45,4); 2,5166 (33,5); 2,4565 (0,5); 2,2931 (0,3); 1,7806 (0,4); 1,5796 (0,4); 1,3758 (1,0); 1,3432 (0,5); 1,3178 (0,6); 1,2941 (0,4); 0,9811 (1,2); 0,9570 (2,2); 0,9316 (0,8); 0,0206 (43,4)_______________________________________________________________________________________________ I.048: 1H-NMR (300,2 MHz, d6-DMSO): δ = 8.7905 (1.2); 8.2496 (0.8); 8.2209 (1.0); 8.0182 (1.0); 7.9896 (0.8); 4.0909 (0.4); 4.0626 (0.5); 4.0389 (0.6); 4.0290 (0.4); 3.3405 (16.0); 2.5351 (2.1); 2.5291 (4.6); 2.5230 (6.3); 2.5169 (4.5); 2.5110 (2.1); 2.0103 (2.4); 1.2199 (0.6); 1.1962 (1.3); 1.1725 (0.6); 0.0214 (4.1) Petition 870250043647, dated 05 / 27 / 2025, pages 120 / 149 117 / 125 1.049:1H-NMR (300.2 MHz, d6-DMSO): δ = 8.7824 (2.2); 8.1934 (1.8); 8.1876 (0.7); 8.1708 (0.8); 8.1648 (2.3); 7.9916 (2.3); 7.9854 (0.7); 7.9687 (0.7); 7.9629 (1.7); 7.7636 (0.7); 7.5920 (1.7); 7.4205 (0.8); 4.0780 (0.8); 4.0160 (1.0); 3.6659 (0.6); 3.6036 (0.5); 3.3478 (16.0); 2.5349 (1.2); 2.5289 (2.4); 2.5229 (3.3); 2.5168 (2.4); 2.5109 (1.1); 0.0200 (3.0) 1.050:1H-NMR (499.9 MHz, d6-DMSO): δ = 9.8743 (0.4); 9.5335 (0.7); 9.4527 (0.8); 9.4450 (0.8); 9.3743 (0.8); 9.3329 (0.8); 9.2243 (0.7); 9.1586 (0.6); 9.1180 (0.6); 9.1009 (0.6); 9.0290 (0.5); 8.9990 (0.5); 8.9855 (0.5); 8.9401 (0.5); 8.8896 (0.5); 8.8570 (0.5); 8.8250 (0.5); 8.7856 (0.5); 8.7352 (0.4); 8.2632 (0.3); 8.0843 (12.8); 8.0676 (16.0); 7.9933 (0.3); 7.9770 (0.4); 7.9684 (0.4); 7.9519 (0.8); 7.9358 (15.6); 7.9191 (12.8); 7.8480 (0.4); 4.0257 (6.7); 3.9886 (8.1); 3.9323 (0.4); 3.9171 (0.5); 3.9023 (0.4); 3.8968 (0.6); 3.8824 (1.8); 3.8676 (2.6); 3.8530 (1.9); 3.8387 (0.5); 3.6443 (5.6); 3.6070 (4.6); 3.4829 (1.1); 3.4671 (3.7); 3.4514 (5.6); 3.4358 (3.8); 3.4201 (1.2); 3.2896 (0.4); 2.6374 (0.3); 2.5029 (58.7); 2.1344 (1.4); 2.1203 (3.1); 2.1107 (4.4); 2.0949 (5.3); 2.0847 (3.6); 2.0709 (2.1); 2.0148 (0.3); 2.0035 (0.4); 1.9547 (1.6); 1.9416 (4.1); 1.9277 (5.6); 1.9161 (4.5); 1.9028 (3.6); 1.8880 (1.7); 1.7952 (1.1); 1.7890 (1.4); 1.7738 (3.6); 1.7697 (4.0); 1.7583 (5.8); 1.7449 (4.7); 1.7271 (2.5);1,7182 (3,2); 1,6995 (5,3); 1,6915 (4,6); 1,6861 (5,8); 1,6768 (4,3); 1,6725 (3,5); 1,6626 (2,1); 1,6521 (1,1); 1,6461 (1,0); 1,6301 (0,5); 1,2324 (1,4); 1,2266 (1,4); 1,2087 (3,2); 1,1944 (5,6); 1,1803 (2,7); -0,0002 (18,0) 1.051:1H-NMR (300,2 MHz, CDCI3):; δ = 8,1980 (0,6); 8,1692 (0,8); 7,8367 (0,8); 7,8079 (0,6); 7,2988 (8,6); 3,7677 (0,4); 3,6387 (0,6); 2,7191 (3,5); 1,5978 (16,0); 0,0480 (0,4); 0,0371 (11,1); 0,0261 (0,4)_________________________________________________ 1.052:1H-NMR (300,2 MHz, CDCI3): δ = 8.2206 (9.7); 8.2146 (3.3); 8.1980 (3.7); 8.1918 (11.3); 8.1747 (3.6); 8.1690 (3.4); 8.1495 (4.4); 8.1433 (4.0); 7.8665 (11.6); 7.8603 (3.7); 7.8437 (3.4); 7.8377 (9.4); 7.6555 (2.4); 7.6503 (3.1); 7.6283 (4.4); 7.6244 (5.2); 7.5883 (2.2); 7.5822 (2.4); 7.5639 (4.4); 7.5577 (4.0); 7.5380 (2.9); 7.5312 (2.7); 7.5264 (3.8); 7.5207 (3.6); 7.5011 (4.1); 7.4960 (4.2); 7.4764 (1.6); 7.4715 (1.4); 7.2988 (54.1); 5.3380 (7.4); 4.1945 (1.1); 4.1706 (3.5); 4.1469 (3.5); 4.1231 (1.2); 3.8434 (3.5); 3.7839 (7.1); 3.6797 (4.2); 3.6762 (4.3); 3.6203 (2.1); 3.6165 (2.1); 3.1613 (0.6); 3.1392 (0.6); 2.0838 (16.0); 1.8666 (0.4); 1.6555 (2.0); 1.4540 (2.0); 1.4296 (3.5); 1.4051 (1.8); 1.3627 (0.5); 1.3400 (0.5); 1.3201 (4.6); 1.2963 (9.5); 1.2725 (4.5); 1.2296 (0.4); 0.8977 (0.6); 0.8770 (0.7); 0.1064 (0.4); 0.0474 (1.2); 0.0366 (46.0); 0.0257 (1.8)__________________________________________________ 1.053:1H-NMR (300.2 MHz, d6-DMSO): δ = 8,7802 (0,7); 8,1068 (1,3); 8,0781 (2,0); 7,9674 (1,9); 7,9386 (1,3); 4,0676 (0,6); 4,0056 (0,8); 3,6564 (0,5); 3,5940 (0,4); 3,3496 (16,0); 2,6244 (6,8); 2,5345 (1,6); 2,5286 (3,3); 2,5225 (4,5); 2,5165 (3,3); 2,5106 (1,6); 0,0202 (2,6)_____________________________________________________________________________________________________ I.054:1H-NMR (500,1 MHz, CDCI3): δ = 8,2130 (3,9); 8,1959 (4,4); 7,9735 (0,7); 7,8674 (4,4); 7,8503 (4,1); 7,2597 (26,8); 7,0713 (0,4); 7,0374 (1,2); 6,9340 (2,8); 6,8307 (1,4); 3,7813 (1,9); 3,7457 (2,8); 3,5891 (1,8); 3,5873 (1,9); 3,5536 (1,2); 3,5517 (1,3); 2,6542 (1,1); 2,3678 (0,9); 2,3528 (1,5); 2,3377 (1,0); 2,0445 (0,6); 1,6532 (0,5); 1,6388 (0,7); 1,6238 (0,6); 1,6087 (0,4); 1,5552 (2,7); 1,3307 (0,5); 1,2989 (1,0); 1,2836 (1,3); 1,2727 (1,9); 1,2553 (16,0); 0,8937 (1,0); 0,8802 (2,6); 0,8660 (1,3); 0,8583 (0,5); 0,8450 (0,6); 0,0062 (0,9); -0,0002 (27,4); -0,0066 (1,3) 1.055:1H-NMR (300,2 MHz, CDCI3): δ = 8,0182 (1,1); 8,0118 (0,7); 7,9895 (1,3); 7,9835 (0,6); 7,9526 (0,9); 7,9451 (0,4); 7,7726 (1,4); 7,7660 (0,8); 7,7439 (1,0); 7,7378 (0,5); 7,2988 (8,2); 7,2924 (2,6); 3,7092 (0,4); 3,6496 (0,8); 3,5281 (0,5); 2,1042 (4,1); 2,0965 (2,4); 1,5411 (16,0); 1,5348 (5,6); 0,0082 (0,7); -0,0024 (12,0); -0,0086 (3,7)_________________ 1.056:1H-NMR (300,2 MHz, CDCI3): δ = 7,8436 (1,3); 7,8331 (1,5); 7,6943 (1,5); 7,6632 (0,9); 7,6350 (1,5); 7,5600 (1,5); 7,5314 (0,9); 7,2988 (8,1); 7,2941 (2,0); 3,7039 (0,4); 3,6448 (0,8); 3,5178 (0,5); 2,0526 (13,1); 2,0479 (3,7); 1,6482 (16,0); 1,6438 (4,7); 1,2574 (0,5); 0,0150 (0,4); 0,0044 (9,1); -0,0002 (2,4)________________________________________ I.057: 1H-NMR (400,2 MHz, d6-DMSO): δ = 8.7214 (1.0); 7.9538 (2.7); 7.9388 (0.8); 7.9041 (0.8); 7.8679 (0.6); 7.8403 (1.0); 7.8145 (1.4); 7.7820 (6.4); 7.7620 (7.5); 7.7286 (0.4); 7.7073 (0.4); 7.6886 (0.4); 7.6706 (0.4); 7.5777 (6.6); 7.5577 (5.6); 7.2820 (0.4); 7.2481 (0.4); 7.2263 (0.4); 5.9989 (0.4); 5.9857 (0.7); 5.9773 (1.1); 5.9644 (1.1); 5.9511 (1.4); 5.9352 (1.4); 5.9213 (1.1); 5.9090 (1.2); 5.2167 (0.5); 5.2108 (0.4); 5.2074 (0.4); 5.1916 (0.5); 5.1418 (3.2); 5.1160 (3.0); 5.0099 (0.3); 4.9834 (0.6); 4.9237 (0.6); 4.8661 (2.8); 4.8233 (2.7); 4.7688 (5.1); 4.7615 (5.0); 4.6230 (0.9); 4.6105 (0.9); 4.5819 (0.7); 4.5692 (0.6); 3.9811 (3.2); 3.9349 (4.0); 3.6026 (2.8); 3.5566 (2.2); 3.3392 (13.6); 3.2022 (0.6); 3.1865 (0.6); 2.8910 (14.4); 2.7486 (0.6); 2.7316 (13.7); 2.6722 (0.5); 2.6679 (0.4); 2.5930 (2.0); 2.5825 (0.6); 2.5074 (67.6); 2.5031 (85.5); 2.4988 (64.2); 2.4701 (2.0); 2.3300 (0.5); 1.3109 (6.7); 1.2953 (1.2); 1.2357 (0.4); 1.2205 (0.4); 1.1862 (0.4); 1.1707 (2.6); 1.1589 (16.0); 1.1339 (2.4);1.0698 (0.6); 0.0080 (0.5); -0.0002 (13.0); -0.0084 (0.6); Petition 870250043647, dated 05 / 27 / 2025, pp. 121 / 149 118 / 125 1.058:1H-NMR (300.2 MHz, CDCI3): δ = 8.2615 (4.3); 8.2325 (4.7); 7.9260 (5.1); 7.8970 (4.0); 7.2983 (30.0); 3.8372 (1.6); 3.8058 (2.0); 3.7776 (2.9); 3.6400 (1.9); 3.5906 (2.8); 3.4802 (0.7); 3.4560 (0.7); 1.5989 (16.0); 1.3695 (0.4); 1.3467 (0.5); 1.2919 (2.5); 1.2588 (1.7); 1.2349 (0.8); 0.9170 (0.3); 0.8967 (0.4); 0.8760 (0.4); 0.0477 (1.3); 0.0369 (36.3); 0.0278 (1.2); 0.0261 (1.3)_____________________________________________________________________________________________________ 1.059:1H-NMR (400.1 MHz, d6-DMSO): δ = 14.2935 (0.3); 11.4664 (0.3); 8.8353 (0.3); 8.7575 (11.1); 8.7003 (0.4); 8.2436 (0.4); 8.2147 (0.8); 8.1830 (13.0); 8.1622 (15.4); 8.1037 (0.5); 8.0540 (0.4); 7.9811 (16.0); 7.9603 (13.4); 7.9122 (1.0); 7.8968 (0.6); 7.8077 (0.3); 4.0542 (6.2); 4.0387 (1.2); 4.0071 (7.8); 3.9813 (0.5); 3.6431 (6.0); 3.5952 (5.1); 3.4238 (11.0); 3.3028 (0.6); 3.2725 (0.5); 3.2566 (0.5); 3.2036 (0.4); 3.1637 (0.4); 3.1030 (0.4); 3.0831 (0.4); 3.0181 (0.4); 3.0055 (0.3); 2.9838 (0.4); 2.6704 (0.6); 2.6083 (0.4); 2.5007 (109.5); 2.4564 (2.8); 2.3815 (0.8); 2.3317(1.1);2.2896 (0.4); 2.2731 (0.4); 1.9880 (1.8); 1.9080 (0.4); 1.2350 (0.9); 1.2122 (0.4); 1.1921 (0.7); 1.1742 (0.9); 1.1570 (0.6); 0.0333 (1.1); -0.0002 (52.6); -0.0483 (0.9); -0.1231 (0.3); -0.1490 (0.4)__________ 1.060:1H-NMR (500.1 MHz, CDCl3): δ = 8.6299 (2.7); 8.6248 (2.7); 8.4410 (1.4); 8.4329 (1.4); 8.1183 (1.8); 8.1018 (2.1); 8.0174 (3.5); 8.0009 (4.0); 7.8693 (0.8); 7.8524 (1.5); 7.8383 (0.7); 7.7490 (3.9); 7.7325 (3.5); 7.4660 (0.4); 7.2595 (67.5); 7.2505 (1.7); 7.2275 (1.2); 7.2176 (1.3); 7.2129 (1.2); 7.2031 (1.1); 7.0480 (0.4); 6.8371 (2.6); 6.8320 (2.7); 3.7852 (1.7); 3.7498 (2.5); 3.5909 (1.7); 3.5556 (1.2); 3.4918 (0.3); 2.5511 (0.6); 1.5451 (16.0); 1.4227 (0.4); 1.4090 (0.4); 1.3581 (0.4); 1.3330 (0.4); 1.2547 (5.9); 1.2147 (0.6); 0.8937 (0.5); 0.8806 (0.8); 0.8663 (0.6); 0.8575 (1.0); 0.8454 (1.2); -0.0002 (60.0); -0.1199 (0.4)________________________________________________________________ 1.061:1H-NMR (400.2 MHz, d6-DMSO): δ = 9.8382 (13.4); 9.8354 (13.6); 8.7338 (2.7); 8.2159 (6.2); 8.2132 (6.4); 8.2034 (6.5); 8.2006 (6.5); 7.9527 (0.4); 7.8663 (10.0); 7.8453 (16.0); 7.7659 (15.7); 7.7450 (10.5); 7.4926 (11.5); 7.4801 (11.3); 4.0245 (5.4); 3.9781 (6.8); 3.6371 (4.1); 3.5907 (3.3); 3.3329 (26.3); 2.8912 (2.3); 2.7315 (2.0); 2.6765 (0.3); 2.6720 (0.4); 2.6677 (0.3); 2.5252 (1.5); 2.5120 (28.3); 2.5076 (55.4); 2.5031 (71.7); 2.4986 (51.6); 2.4941 (25.1); 2.3299 (0.4); 1.2391 (0.5); -0.0002 (5.2)___________________________________________________________________ 1.062:1H-NMR (400.2 MHz, d6-DMSO): δ = 9.9981 (3.3); 9.9951 (3.3); 8.6814 (1.8); 8.6166 (1.6); 8.6134 (2.8); 8.6101 (1.9); 8.5853 (3.0); 8.5816 (2.4); 7.9543 (2.3); 7.9312 (2.7); 7.9100 (3.9); 7.8235 (4.0); 7.8024 (2.7); 4.0046 (1.4); 3.9583 (1.8); 3.6242 (1.1); 3.5778 (0.9); 3.3385 (19.0); 2.8919 (16.0); 2.7328 (13.7); 2.5130 (7.4); 2.5087 (14.1); 2.5042 (17.8); 2.4997 (12.7); 2.4953 (6.2); -0.0002 (1.0)________________________________________________________________ 1.063:1H-NMR (400.2 MHz, d6-DMSO): δ = 9.7267 (10.2); 8.7179 (2.4); 7.9535 (1.9); 7.8521 (4.8); 7.8313 (6.8); 7.7260 (6.6); 7.7052 (4.7); 7.2253 (4.6); 7.2237 (4.4); 4.0199 (2.4); 3.9734 (3.0); 3.6300 (1.9); 3.5836 (1.5); 3.3375 (29.2); 2.8917 (13.5); 2.7323 (11.7); 2.5827 (16.0); 2.5257 (0.5); 2.5122 (11.5); 2.5080 (22.4); 2.5036 (28.7); 2.4991 (20.7); 2.4948 (10.3); -0.0002 (1.5)________________________________________________________________________________ 1.064:1H-NMR (600.2 MHz, d6-DMSO): δ = 8.8746 (2.4); 8.2900 (0.5); 8.2772 (0.6); 8.2294 (1.0); 8.1904 (14.5); 8.1774 (15.8); 7.9658 (16.0); 7.9528 (14.6); 4.0270 (6.1); 3.9961 (7.1); 3.6345 (6.9); 3.6035 (6.0); 3.3267 (2.4); 3.1684 (0.8); 2.5526 (0.5); 2.5078 (21.4); 2.4466 (44.3); 2.3365 (0.4); 1.5737 (0.8); 1.3226 (0.8); 1.3109 (0.9); 0.9543 (1.2); 0.9427 (2.0); 0.9313 (1.1)________________________________________________________________________________ 1.065:1H-NMR (300.2 MHz, CDCl 3 ): δ = 7.9344 (1.0); 7.9054 (1.2); 7.6948 (1.3); 7.6673 (1.0); 7.6657 (1.0); 7.2987 (10.1); 5.7105 (0.8); 3.8346 (0.3); 3.7747 (0.9); 3.7073 (0.6); 1.5949 (7.6); 1.5526 (16.0); 1.2910 (0.4); 0.0480 (0.5); 0.0464 (0.4); 0.0372 (14.1); 0.0281 (0.5); 0.0264 (0.5)_________________________________________________________________________ 1.066:1H-NMR (400.2 MHz, d6-DMSO): δ = 9.1551 (4.5); 8.6972 (3.5); 8.6480 (0.5); 8.4609 (5.2); 7.9556 (3.3); 7.8377 (2.2); 7.8167 (7.8); 7.8028 (7.6); 7.7818 (2.2); 7.7369 (0.6); 7.7204 (0.6); 7.5052 (1.0); 7.4871 (0.6); 4.0002 (2.2); 3.9686 (0.6); 3.9538 (2.8); 3.9224 (0.5); 3.6142 (2.0); 3.5677 (1.7); 3.3428 (18.7); 2.8924 (16.0); 2.7507 (0.4); 2.7333 (15.8); 2.5054 (35.2); 1.2445 (0.8); 1.2083 (1.1); 1.1859 (1.4); 1.1705 (1.3); 1.1648 (1.5); 1.1534 (1.9); 1.1315 (1.2); 1.1200 (1.3); 1.0970 (0.5); 1.0716 (0.4); -0.0002 (2.4)___________________________________________________ I. 067: 1H-NMR (400.2 MHz, d6-DMSO): δ = 8.7258 (8.7); 8.6499 (9.3); 8.6462 (9.4); 7.9555 (0.6); 7.9249 (9.1); 7.9214 (9.1); 7.8973 (6.0); 7.8763 (16.0); 7.8535 (15.6); 7.8324 (5.9); 4.0188 (4.9); 3.9724 (6.2); 3.6296 (4.3); 3.5830 (3.5); 3.3496 (54.1); 2.8930 (3.1); 2.7340 (2.9); 2.5103 (36.3); 2.5063 (45.0); 2.5022 (34.6); 1.1706 (0.3); -0.0002 (3.3) Petition 870250043647, dated 05 / 27 / 2025, pp. 122 / 149 119 / 125 1.068:1H-NMR (400,2 MHz, d6-DMSO): δ = 9,5040 (14,6); 9,4914 (1,2); 9,1502 (16,0); 9,1370 (1,2); 8,6853 (9,3); 7,9582 (9,9); 7,9375 (13,1); 7,8178 (13,0); 7,7970 (10,2); 4,0053 (5,3); 3,9589 (6,6); 3,6258 (4,6); 3,5793 (3,6); 3,3597 (111,7); 2,8926 (2,1); 2,7338 (2,0); 2,5107 (35,8); 2,5065 (45,8); 2,5024 (36,6)_____________________________________________ 1.069:1H-NMR (300,2 MHz, CDCI3): δ = 7,9823 (2,6); 7,9535 (2,8); 7,7515 (3,2); 7,7241 (2,2); 7,2986 (38,2); 4,8934 (1,1); 3,8171 (0,9); 3,7579 (1,9); 3,6484 (1,2); 3,5912 (0,6); 2,3064 (0,4); 2,2906 (0,4); 2,2810 (1,0); 2,2599 (0,5); 1,5943 (16,0); 1,3051 (6,0); 1,2900 (3,1); 1,2780 (2,4); 0,8974 (0,4); 0,8777 (0,4); 0,0477 (1,9); 0,0369 (54,6); 0,0260 (2,0) 1.070:1H-NMR (300,2 MHz, CDCI3): δ = 7.8502 (0.8); 7.8461 (0.8); 7.6883 (0.5); 7.6601 (0.8); 7.5804 (0.8); 7.5520 (0.4); 7.2986 (19.6); 4.0868 (0.8); 4.0632 (0.8); 3.7593 (0.4); 3.7446 (0.4); 1.5873 (16.0); 1.2894 (0.5); 0.7535 (0.3); 0.7302 (0.3); 0.4766 (0.4); 0.4572 (0.4); 0.0478 (1.0); 0.0371 (27.8); 0.0263 (1.2)__________________________________________________ I.071: 1H-NMR (300.2 MHz, CDCl3): δ = 7.8683 (2.5); 7.7674 (14.8); 7.7566 (5.3); 7.6416 (5.6); 7.6159 (8.6); 7.6057 (3.4); 7.5149 (8.2); 7.5069 (4.2); 7.4892 (6.0); 7.3011 (20.7); 7.2974 (17.8); 7.2888 (7.1); 3.6759 (2.8); 3.6608 (1.6); 3.6461 (1.9); 3.6356 (2.8); 3.6180 (6.1); 3.4929 (3.9); 3.4334 (2.1); 2.5648 (0.9); 2.2054 (16.0); 1.9995 (0.3); 1.2379 (2.4); 1.1934 (1.0); 1.1804 (1.9); 1.1631 (5.1); 1.1538 (5.8); 1.1509 (5.8); 1.1376 (3.5); 1.1150 (1.0); 1.1028 (1.1); 1.0870 (2.4); 1.0706 (4.2); 1.0664 (4.5); 1.0461 (4.8); 1.0236 (1.5); 0.8257 (0.5); -0.0138 (30.4); 0.0174 (27.9); -0.0260 (11.6); -0.0803 (0.4) BIOLOGICAL DATA Example: preventive in vivo test in Puccinia recondita (brown rust in wheat) Solvent: 5% by volume of dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

[0252] The active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide / acetone / / Tween® 80 and then diluted in water to the desired concentration.

[0253] Young wheat plants were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone / dimethyl sulfoxide / Tween® 80.

[0254] After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants were incubated for 24 hours at 20 °C and 100% relative humidity and then for 9 days at 20 °C and 70-80% relative humidity. Petition 870250043647, dated 05 / 27 / 2025, pp. 123 / 149 120 / 125

[0255] The test was evaluated 10 days after inoculation. 0% means an efficacy that corresponds to that of the control plants, while an efficacy of 100% means that no disease was observed.

[0256] In this test, the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 250 ppm of active ingredient: I.012; I.013; I.037

[0257] In this test, the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 250 ppm of active ingredient: I.008; I.011; I.020; I.022; I.032; I.038; I.046; I.048; I.052

[0258] In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 250 ppm of active ingredient: I.015; I.049; I.051; I.053; I.058; I.066; I.067; I.068 Example: preventive in vivo test on Phakospora pachyrhizi (soybean rust) Solvent: 5% by volume of dimethyl sulfoxide 10% by volume of acetone Emulsifier: 1 μl of Tween® 80 per mg of active ingredient

[0259] The active ingredients were made soluble and homogenized in a mixture of dimethyl sulfoxide / acetone / / Tween® 80 and then diluted in water to the desired concentration.

[0260] Young soybean plants were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone / dimethyl sulfoxide / Tween® 80.

[0261] After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Phakospora pachyrhizi spores. The plants Petition 870250043647, dated 05 / 27 / 2025, pp. 124 / 149 121 / 125 contaminated soybeans were incubated for 24 hours at 24 °C and 100% relative humidity and then for 10 days at 24 °C and 70-80% relative humidity.

[0262] The test was evaluated 11 days after inoculation. 0% means an efficacy that corresponds to that of the control plants, while an efficacy of 100% means that no disease was observed.

[0263] In this test, the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 250 ppm of active ingredient: I.016; I.026; I.044; I.046; I.056

[0264] In this test, the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 250 ppm of active ingredient: I.007; I.021; I.025; I.027; I.032; I.040

[0265] In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 250 ppm of active ingredient: I.003; I.011; I.022; I.034; I.036; I.037; I.038; I.041; I.042; I.049; I.051; I.053; I.058; I.066; I.067; I.068; I.069; I.070 Example: In vitro cell test for Pyricularia oryzae Solvent: DMSO Culture Medium: 14.6 g of anhydrous D-glucose (VWR), 7.1 g of mycological peptone (oxoid), 1.4 g of granulated yeast extract (Merck), QSP 1 liter Inoculum: spore suspension

[0266] The fungicides were solubilized in DMSO and the solution was used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <1%.

[0267] A P. oryzae spore suspension was prepared and diluted to the desired spore density.

[0268] The fungicides were evaluated for their ability to inhibit spore germination and mycelial growth in a liquid culture assay. The Petition 870250043647, dated 05 / 27 / 2025, pages 125 / 149 122 / 125 compounds were added at the desired concentration to the spore culture medium. After 5 days of incubation, the toxicity of the compounds to fungi was determined by spectrometric measurement of mycelial growth. Inhibition of fungal growth was determined by comparing absorbance values ​​in wells containing the fungicides with absorbance in control wells without fungicides.

[0269] In this test, the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 20 ppm of active ingredient: I.015; I.018; I.022; I.038

[0270] In this test, the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 20 ppm of active ingredient: I.004; I.006; I.011; I.021; I.040; I.052; I.058; I.063

[0271] In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 20 ppm of active ingredient: I.003; I.009; I.016; I.019; I.029; I.036; I.039; I.043; I.044; I.045; I.049; I.067. Example: In vitro cell test of Colletotrichum lindemuthianum. Solvent: DMSO. Culture Medium: 14.6 g of anhydrous D-glucose (VWR), 7.1 g of mycological peptone (Qxoid), 1.4 g of granulated yeast extract (Merck), QSP 1 liter Inoculum: spore suspension

[0272] The fungicides were solubilized in DMSO and the solution was used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was <1%.

[0273] A spore suspension of C. lindemuthianum was prepared and diluted to the desired spore density.

[0274] The fungicides were evaluated for their ability to inhibit spore germination and mycelial growth in a liquid culture assay. The Petition 870250043647, dated 05 / 27 / 2025, pages 126 / 149 123 / 125 compounds were added at the desired concentration to the spore culture medium. After 6 days of incubation, the toxicity of the compounds to fungi was determined by spectrometric measurement of mycelial growth. Inhibition of fungal growth was determined by comparing absorbance values ​​in wells containing the fungicides with absorbance in control wells without fungicides.

[0275] In this test, the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 20 ppm of active ingredient: I.001; I.007; I.012; I.031; I.048; I.057; I.060; I.070

[0276] In this test, the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 20 ppm of active ingredient: I.002; I.013; I.015; I.016; I.017; I.018; I.023; I.024; I.025; I.026; I.032; I.034; I.037; I.038; I.040; I.042; I.044; I.049; I.061; I.062; I.063; I.069

[0277] In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 20 ppm of active ingredient: I.003; I.006; I.009; I.011; I.019; I.021; I.022; I.029; I.036; I.039; I.041; I.043; I.045; I.046; I.051; I.056; I.058; I.066; I.067; I.068 Example: preventive in vivo test in Phakopsora test (soybean) Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethyl sulfoxide Emulsifier: 1 part by weight of polyoxyethylene sorbitan monooleate

[0278] To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the indicated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.

[0279] To test the preventive activity, young plants were sprayed with the active compound preparation at the indicated application rate. After the spray coating dried, the plants were inoculated with Petition 870250043647, dated 05 / 27 / 2025, pages 127 / 149 124 / 125 an aqueous suspension of spores of the causal agent of soybean rust (Phakopsora pachyrhizi) and remained for 24 h without light in an incubation chamber at approximately 24 °C and 95% relative humidity.

[0280] The plants remained in the incubation chamber with a temperature of approximately 24 °C and relative air humidity of approximately 80% and a day / night interval of 12h.

[0281] The test was evaluated 7 days after inoculation. 0% means an efficacy that corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. Example: in vivo curative test in Phakopsora (soybean) test Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethyl sulfoxide Emulsifier: 1 part by weight of polyoxyethylene sorbitan monooleate

[0282] To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the indicated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.

[0283] To test the curative activity, young plants were inoculated with an aqueous suspension of spores of the causal agent of soybean rust (Phakopsora pachyrhizi) and remained for 24 hours without light in an incubation chamber at approximately 24 °C and 95% relative humidity.

[0284] The plants remained in the incubation chamber with a temperature of approximately 24 °C and relative air humidity of approximately 80% and a day / night interval of 12h.

[0285] 2 days after inoculation, the plants were sprayed with the active compound preparation at the indicated application rate and remained thereafter in the incubation chamber. Petition 870250043647, dated 05 / 27 / 2025, pages 128 / 149 125 / 125

[0286] The test was evaluated 7 days after inoculation. 0% means an efficacy that corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. Example: long-duration in vivo activity test in Phakopsora (soybean) test Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethyl sulfoxide Emulsifier: 1 part by weight of polyoxyethylene sorbitan monooleate

[0287] To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the indicated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.

[0288] To test long-term activity, young plants were sprayed with the active compound preparation at the indicated application rate. After the spray coating dried, the plants were placed in an incubation chamber at approximately 24 °C and a relative humidity of approximately 80% and a 12-hour day / night interval.

[0289] 8 days after application, the plant was inoculated with an aqueous suspension of spores of the causal agent of soybean rust (Phakopsora pachyrhizi) and remained for 24h without light in the incubation chamber at approximately 24 °C and relative air humidity of 95%.

[0290] The plants remained in the incubation chamber with a temperature of approximately 24 °C and relative air humidity of approximately 80% and a day / night interval of 12h.

[0291] The test was evaluated 7 days after inoculation. 0% means an efficacy that corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

Claims

1. Compound CHARACTERIZED by the fact that it is of formula (I): wherein R1 is hydrogen, acetyl or 2-methoxyacetyl; X is a fluorine or chlorine atom; m is 0 or 1; Het is a 5-membered heteroaryl selected from the group consisting of furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl and triazolyl; n is 1 or 2; R2 is a substituent independently selected from the group consisting of cyano, C1-C4-haloalkyl, C1-C4-alkoxy, C2-C4-alkenyl, C3-C6-cycloalkyl, phenyl which may be substituted by one or two halogen substituents, thienyl, pyridinyl, formyl, C1-C4-alkylcarbonyl, carboxy-C1-C4-alkyl, C1-C4-alkoxycarbonyl, -CH2-cyclopropyl, -CH2-(N-morpholinyl), benzyl, -CH2-thienyl, -CH2-pyridinyl, -C1-C4-alkyl-C1C4-alkoxy, -C1-C4-alkyl-C(=O)O-C1-C4-alkyl; or a salt or N-oxide thereof.

2. Compound of formula (I), according to claim 1, CHARACTERIZED in that X is a fluorine atom. Petition 870260054234, dated 03 / 06 / 2026, page 7 / 15 2 / 2 3. Composition CHARACTERIZED in that it comprises at least one compound of formula (I), as defined in claim 1 or 2, and at least one agriculturally acceptable carrier.

4. Use of a compound of formula (I), as defined in claim 1 or 2, or a composition, as defined in claim 3, CHARACTERIZED in that it is for the control of phytopathogenic fungi in plants.

5. Method for controlling phytopathogenic fungi CHARACTERIZED in that it comprises the step of applying at least one compound of formula (I), as defined in claim 1 or 2, or a composition, as defined in claim 3, to plants, plant parts, seeds, fruits or the soil in which the plants grow.