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

Abstract

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

Description

"Hydroxyisoxazolines, composition, use thereof and method for controlling phytopathogenic fungi" FIELD OF TECHNIQUE

[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] Isoxazole derivatives are known to be useful as agricultural crop protection agents to combat or prevent infestations of microorganisms. For example, document no. WO2015 / 129773 discloses isoxazole derivatives that can be used as fungicides. Document no. 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 revealed as useful for controlling phytopathogenic fungi (document no. WO2018 / 202487).

[003] Several fungicidal agents have been developed to date. However, there is still a need for the development of new fungicidal compounds to meet the growing environmental and economic demands placed on modern agricultural 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 870250021756, dated 03 / 19 / 2025, page 5 / 233 2 / 107 SUMMARY

[005] The present invention relates to compounds of formula (I): (I)

[006] Where R1, R2, X, m, ne Cy are as recited in this document as well as their salts, N-oxides and solvates.

[007] 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.

[008] 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

[009] The term “alkyl” as used in this document in the context of alkyl or alkylsulfonyl, alkylsulfinyl, alkylthio, alkylamino, for example, shall be understood to mean preferably branched or unbranched alkyl, meaning, e.g., 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.

[010] The term “haloalkyl” as used in this document will preferably be understood to mean branched and unbranched alkyl, as defined above, wherein one or more of the hydrogen substituents are Petition 870250021756, dated 03 / 19 / 2025, p. 6 / 233 3 / 107 substituted in the same or different ways by halogen. Particularly, preferably, said haloalkyl is, e.g., chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromobutyl, trifluoromethyl, iodoethyl and isomers thereof.

[011] The term “alkoxy” as used in this document will preferably be understood to mean branched and unbranched alkoxy, meaning, e.g., methoxy, ethoxy, propyloxy, / so-propyloxy, butyloxy, / so-butyloxy, tert-butyloxy, sec-butyloxy, pentyloxy, / so-pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy and dodecyloxy and isomers thereof.

[012] The term “haloalkoxy” as used in this document will preferably be understood to mean branched and unbranched alkoxy, as defined above, in which one or more of the hydrogen substituents are substituted in the same or different ways by halogen, e.g., chloromethoxy, fluoromethoxy, pentafluoroethoxy, fluoropropyloxy, difluoromethyloxy, trichloromethoxy, 2,2,2-trifluoroethoxy, bromobutyloxy, trifluoromethoxy, iodoethyloxy, and isomers thereof.

[013] The term “carbocyclyl” as used herein refers to a non-aromatic (fused, spiro or bridging) mono- or polycyclic carbon-containing ring, which may be saturated or partially unsaturated, having 3 to 10 carbon atoms in the ring or 3 to 7 carbon atoms in the ring. Examples of carbocyclyl include cycloalkyl and cycloalkenyl groups. Examples of saturated carbocyclyl, herein also referred to 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, cycloeptenyl, cyclooctenyl, cyclononenyl or cyclodecenyl groups, wherein the said cycloalkyl group is attached to the rest of the molecule. Petition 870250021756, dated 03 / 19 / 2025, p. 7 / 233 4 / 107 can be supplied as a double or single connection.

[014] The term “heterocycline” as used in this document refers to saturated or partially unsaturated heterocycles of three to ten members, preferably three to nine members (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 groups include, but are not limited to, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,. 1,2,4-thiadiazolidin-3-ila, 1,2,4-thiadiazolidin-5-ila, 1,2,4-triazolidin-3-ila, 1,3,4oxadiazolidin-2-ila, 1,3,4-thiadiazolidin-2-ila, 1,3,4-triazolidin-2-ila, 2,3-dihydrofur-2-ila, 2,3-di-hidrofur-3-ila, 2,4-di-hidrofur-2-ila, 2,4-di-hidrofur-3-ila, 2,3-di-hidrotien-2-ila, 2,3-di-hydrotien-3-ila, 2,4-di-hydrotien-2-ila, 2,4-di-hydrotien-3-ila, 2-pyrroline-2-ila, 2pyrroline-3-ila, 3-pyrroline-2-ila, 3-pyrroline-3-ila, 2-isoxazolin-3-ila, 3-isoxazolin-3-ila, 4isoxazolin-3-ila, 2-isoxazolin-4-ila, 3-isoxazolin-4-ila, 4-isoxazolin-4-ila, 2-isoxazolin5-ila, 3-isoxazolin-5-ila, 4-isoxazolin-5-ila, 2-isothiazolin-3-ila, 3-isothiazolin-3-ila, 4isothiazolin-3-ila, 2-isothiazoline-4-ila, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-di-hydropyrazol-1-yl, 2,3-di-hydropyrazol2-yl, 2,3-di-hydropyrazol-3-yl, 2,3-di-hydropyrazol-4-yl, 2,3-di-hydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, hydropyrazol-5-yl, hydropyrazol-4-yl, 3,4-di-hydropyrazol-3-yl, 3,4-di-hydropyrazol-4-yl, 3,4-di4,5-di-hydropyrazol-1-yl, 4,5-di-hydropyrazol-3-yl, 4,5-di 4,5-di-hydropyrazol-5-yl, 2,3-di-hydro-oxazol-2-yl, 2,3-di-hydro Petição 870250021756, de 03 / 19 / 2025, pág. 8 / 233 5 / 107 oxazol-3-ila, 2,3-di-hidro-oxazol-4-ila, 2,3-di-hidro-oxazol-5-ila, 3,4-di-hidro-oxazol-2ila, 3,4-di-hidro-oxazol-3-ila, 3,4-di-hidro-oxazol-4-ila, 3,4-di-hidro-oxazol-5-ila, 3,4-dihidro-oxazol-2-ila, 3,4-di-hidro-oxazol-3-ila, 3,4-di-hidro-oxazol-4-ila, 2-piperidinila, 3piperidinila, 4-piperidinila, 1,3-dioxan-5-ila, 2-tetraidrotienila, 4-tetraidrotienila, 2tetraidrotienila, 3-hexaidropiridazinila, 4-hexaidropiridazinila, 2-hexaidropirimidinila, 4hexaidropirimidinila, 5-hexaidropirimidinila, 2-piperazinila, 1,3,5-hexaidrotriazin-2-ila, 1,2,4-hexaidrotriazin-3-ila, indol-1-ila, indol-2-ila, indol-3-ila, indol-4-ila, indol-5-ila, indol-6-ila, 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-6ila, indazol-7-ila, indazol-2-ila, 1-benzofuran-2-ila, 1-benzofuran-3-ila, 1-benzofuran4-ila, 1-benzofuran-5-ila, 1-benzofuran-6-ila, 1-benzofuran-7-ila, 1-benzotiofen-2-ila,1-benzothiophen-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-4yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl, quinolin-2-yl, quinolin-3-ila, quinolin-4-ila, quinolin-5-ila, quinolin-6-ila, quinolin-7-ila, quinolin-8-ila, isoquinolin-1-ila, isoquinolin-3-ila, isoquinolin-4-ila, isoquinolin-5-ila, isoquinolin-6-ila, isoquinolin-7-ila and isoquinolin-8-yl. This definition also applies to heterocyclyl as part of a composite substituent, for example, heterocyclylalquila, etc., except where otherwise defined.

[015] The term “halogênio” or “Hal” as used in this document must be understood as meaning flavour, chlorine, bromine or iodine.

[016] The term “halo” in square brackets (e.g., “C1-C6-(halo)alkyl”) designates the optional presence of one or more halogen substituents that may be the same or different.

[017] The term “alkenyl” as used in this document will preferably be understood to mean branched and unbranched alkenyl, Petition 870250021756, dated 03 / 19 / 2025, p. 9 / 233 6 / 107 p. e.g., a vinyl group, propen-1-yl, propen-2-yl, but-1-en-1-yl, but-1-en-2-yl, but-2en-1-yl, but-2-en-2-yl, but-1-en-3-yl, 2-methyl-prop-2-en-1-yl or 2-methyl-prop-1-en-1yl.

[018] The term “alkynyl” as used in this document will preferably be understood to mean branched and unbranched alkynyl, e.g., an ethynyl group, prop-1-yn-1-yl, but-1-yn-1-yl, but-2-yn-1-yl or but-3-yn-1-yl.

[019] The term “aryl” as used herein refers to an aromatic hydrocarbon ring system comprising from 6 to 15 carbon atoms, or from 6 to 12 carbon atoms, preferably from 6 to 10 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 by one or more substituents, said substituent (or substituents) may be in any positions on said aryl ring (or rings). In particular, in the case of aryl being a phenyl group, said substituent (or substituents) 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).

[020] The term “heteroaryl” as used in this document refers to an aromatic ring system containing 5 to 15 atoms in the member, or 5 to 12 atoms in the member, whose carbons and one or more heteroatoms, which may be identical or different, are selected from O, N, and S. If the ring contains more than one oxygen atom, they are not directly adjacent. Heteroaryl may be monocyclic or polycyclic (e.g., bicyclic or tricyclic). A monocyclic heteroaryl may have 1 to 4 heteroatoms in the ring, while a polycyclic heteroaryl ring may have 1 to 10 heteroatoms. Bicyclic heteroaryl rings may contain Petition 870250021756, dated 03 / 19 / 2025, p. 10 / 233 7 / 107 from 8 to 15, or from 8 to 12 nonmember atoms (carbon and heteroatoms). A monocyclic heteroaryl can contain from 5 to 8 nonmember atoms. Exemplary heteroaryls include, but are not limited to, thienyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia4H-pyrazolyl etc., and benzo derivatives mesmas, as, p. ex.,, 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 of the same; or cinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthpyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xantenyl or oxepinyl, etc.It is further understood that in the case where the aforementioned heteroaryl group is replaced by one or more substituents, the said substituent (or substituents) may occupy any one or more positions in the said heteroaryl ring (or rings). In particular, if the heteroaryl group is a pyridyl group, for example, the said substituent (or substituents) 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 the heteroaryl group as part of a compound substituent (e.g., heteroaryloxy).

[021] As used in this document, the term “Ci-Cg”, e.g., in the context of the definition of “C1-C6-alkyl” or “C1-C6-alkoxy”, will be understood to mean a group having a finite number of carbon atoms from 1 to 6, i.e., 1, 2, 3, 4, 5 or 6 carbon atoms.

[022] The terms “acyclic radicals” as used in this document in the expressions “in which acyclic radicals may be substituted” mean any of the acyclic groups mentioned in the paragraph preceding said expressions, or any acyclic chemical portion of a composite group (e.g., the C1-C8-alkyl chemical portion of aryl-C1-C8-alkyl). Petition 870250021756, dated 03 / 19 / 2025, p. 11 / 233 8 / 107

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

[024] In the group containing an acyclic chemical moiety and a cyclic chemical moiety (e.g., aryl-C1-C6-alkyl), wherein each of these chemical moieties can be substituted independently of the others.

[025] The term “leaving group” as used in this document will 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

[026] The present invention relates to compounds of formula (I): (I)

[027] in which

[028] R1 is selected from the group that consists of hydrogeny, C1Cs-alquil, Ca-Cs-cycloalquila, C2-C8-alquila, C2-C8-alquinila, -C1-C8-alquil-aryla, -CiC8-alquil-C1-C8-alcoxy, -Si(C1-Ce-alquila)3, -SiAryl(C1-Ce-alquila)2, -C1-C8-alquil-C3-Cecycloalquila, aryla, heteroaryla, -C1-C8-alquil- heteroaryla, di-C1-C8-alkylphosphate, C(=O)Ra, -C(=O)N(Ra)2, -C1-C6-alquil-OC(=O)Rae -C1-C6-alquil-C(=O)Ra, com Ra Petition 870250021756, 19 / 03 / 2025, pág. 12 / 233 9 / 107 being selected starting from the group that consists of hydrogeny, amino, C1-C10alquila, C1-C6-haloalquila, C2-C8-alquenila, C2-C8-haloalquila, C2-C8-alquinila, C2C8-haloalquinila, C1-C8-alcoxila, C1-C8-haloalkóxi, C1-C8-alquilsulfanila, C1-C8alquilamino, di-C1-C8-alquilamino, -C1-C6-alquil-C1-C6-alcoxila, C3-C10-carbociclila, C3C10-halocarbociclila, 3 to 10 membered heterocyclila, aryla, heteroarila, heterociclilóxi, arilóxi and heteroarilóxi,

[029] in which R1 or Raacyclic radicals can be replaced by one or more R1a substituents and in which R1 or Racyclic radicals can be replaced by one or more R1c substituents;

[030] X is a hydrogen, fluorine, or chlorine atom;

[031] m is 0, 1 or 2;

[032] Cy is an 8, 9 or 10 membered bicyclic heteroaryl, 8, 9 or 10 membered fused bicyclic heterocyclyl, C10-aryl bicyclic or C9-C10-fused bicyclic carbocyclyl;

[033] n is 0, 1, 2, 3 or 4;

[034] R2 is an independently selected substituent from the group consisting of halogênio, cyano, hydroxy, sulfanyl, sulfinyl, sulfonyl, amino, nitro, oxo, C1-C6-alquila, C1-C6-haloalquila, C1-C6-hydroxyalquila, C1-C6-cyanoalquila, C1-C6alkóxi, C1-C6-haloalkóxi, C1-C6-alquilamino, di-C1-C6-alquilamino, C2-C6-alquenila, C2-C6-haloalquenila, C2-C6-hidroxialquenila, C2-C6-cyanoalquenila, C2-C6-alquinila, C2-C6-haloalquinyl, C2-C6-hidroxialquinila, C2-C6-cyanoalquinila, C1-C6-alquilsulfanila, pentafluoro-X6-sulfanila, arylsulfanila, C1-C6-alquilsulfonila, arylsulfonila, C1-C6alquilsulfonila, arylsulfonila, C3-C10-carbociclila, heterociclila de 3 a 10 members, aryl, heteroaryl, C3-C10-carbociclilíoxi, heterociclilóxi de 3 a 10 members, arylóxi, heteroarylóxi, -Si(C1-Ce-alquil)3, -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(=NR21)R21, C(=NR21)N(R21)2, -C(=NOR21)R21, -N(R21)2, -NR21C(=O)OR21, -N(OR21)C(=O)OR21,Petition 870250021756, of 19 / 03 / 2025, p. 13 / 233, 10 / 107 NR21C(=O)N(R21)2, -NR21C(=O)R21, -N(OR21)C(=O)R21, -NR21C(=S)R21, NR21C(=S)N(R21)2, -NR21C(=NR21)R21, -OC(=O)RO21,(O NR21S(=O)2R21, -N=CR21-N(R21)2, -S(=O)2R21, -S(=O)2N(R21)2, -P(=O)(OR21)2, =N(OR21), -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-heterocyclyl of 3 to 10 members, C1-C6-(halo)alkyl-O-30-acyl members, -C1-C6-(halo)alkyl-aryl, -C1C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-heteroaryloxy, -C1-C6-(halo)alkyl-OR21, -C1-C6-(halo)alkyl-C(=O)R21, -C1-C6-(halo)alkyl-C(=O)OR21, -C1-Ce-(halo)alkylC(=O)N(R21)2, -C1-C6-(halo)alkyl-C(=O)R21,1 -C1-Ce-(halo)alkylC(=O)NR21N(R21)2, -C1-C6-(halo)alkyl-C(=S)N(R21)2, -C1-C6-(halo)alkylC(=NR21)R21, -C1-C6-(halo)alkyl-C(=NR21)(=R21)2 -C1-C6-(halo)alkyl-C(=NOH)R21, C1-C6-(halo)alkyl-N(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)OR21, -C1-Ce-(halo)alkylN(OR21)C(=O)OR21, -C1-C6-(halo)alkyl-NR21C(=O)N(R21)2, -C1-C6-(halo)alkylNR21C(=O)R21, -C1-C6-(halo)alkyl-N(OR21)C(=O)R21, -C1-Ce-(halo)Cl(=SNR21), -C1-C6-(halo)alkyl-NR21C(=S)N(R21)2, -C1-Ce-(halo)alkylNR21C(=NR21)R21, -C1-C6-(halo)alkyl-OC(=O)R21, -C1-C6-(halo)alkyl-OC(=O)2,2 -C1-C6-(halo)alkyl-NR21S(=O)2R21, -C1-C6-(halo)alkyl-N=CR21-N(R21)2, -C1-C6(halo)alkyl-SR21, -C1-C6-(halo)alkyl-S(=O)R21, -C1-C6-(halo)alkyl-S(=O)OR21, -C1C6-(halo)alkyl-S(=O)2R21, -C1-C6-(halo)alkyl-S(=O)2OR21, -C1-C6-(halo)alkylS(=O)2N(R21)2 and -C1-C6-(halo)alkyl-P(=O)(OR21)2,wherein R21 is selected independently 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,

[035] in which acyclic radicals R2 and R21 can be replaced by one or more R22a substituents and cyclic radicals R2 and R21 can be replaced by one or more R22c substituents,

[036] R1a, R22a, R1ce R22c are selected independently of Petition 870250021756, dated 03 / 19 / 2025, p. 14 / 233 11 / 107 group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-76-sulfanyl, formyl, carbamoyl, carbamate, C1-C6-alkyl, C3C7-cycloalkyl, C1-C6-haloalkyl, C3-C8-halocycloalkyl, C2-C6-(halo)alkenyl, C2C6-(halo)alkynyl, C1-C6-alkylamino, di-C1-C6-alkylamino, -Si(C1-C6-alkyl)3, C1-C6(halo)alkoxy, C1-C6-(halo)alkylsulfanyl, 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)alkylsulfanyl, C1-C8-(halo)alkylsulfinyl, C1-C8-(halo)alkylsulfonyl, C1-C8alkylsulfonylamino, C1-C8-haloalkylsulfonylamino, sulfamoyl, C1-C8-alkylsulfamoyl and di-C1-C8-alkylsulfamoyl;

[037] since the compost gives formula (I) it does not say:

[038] 3-[4-(1 H-indol-6-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol,

[039] 3-[4-(1 H-indazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol,

[040] 3-[4-(2,3-di-hydro-1-benzofuran-5-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro1,2-oxazol-5-ol,

[041] 3-[4-(1-methyl-1 H-indazol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2oxazol-5-ol,

[042] 3-[4-(2,2-difluoro-1,3-benzodioxol-4-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol,

[043] 3-[4-(1-methyl-1 H-indol-5-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol5-ol,

[044] 3-[4-(1-benzothiophene-5-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5ol,

[045] 3-[4-(1-methyl-1 H-indazol-6-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2oxazol-5-ol, and

[046] 3-[4-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-3-yl)phenyl]-5-(trifluoromethyl)4,5-di-hydro-1,2-oxazol-5-ol. Petition 870250021756, dated 3 / 19 / 2025, p. 15 / 233 12 / 107

[047] The excluded compounds are disclosed in WO paper No. 2019 / 122393.

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

[049] Compounds resulting from combinations that are contrary to natural laws and which a person skilled in the art would therefore exclude based on their specialized knowledge are not covered in this document. For example, ring structures having three or more adjacent oxygen atoms are excluded.

[050] 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 encompasses pure stereoisomers and any mixture of these isomers. When a compound may be present in two or more tautomeric forms in equilibrium, reference to the compound by means of a tautomeric description should be considered as including all tautomeric forms.

[051] Any of the compounds of the present invention may also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. Geometric isomers by nature of 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.

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

[053] 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, as an agrochemically active salt. Petition 870250021756, dated 03 / 19 / 2025, p. 16 / 233 13 / 107

[054] Agrochemically active salts include acidic 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, and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid, and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or di-unsaturated fatty acids having 6 to 20 carbon atoms, alkylsulfuric monoesters, alkylsulfonic acids (sulfonic acids having linear or branched chain alkyl radicals with 1 to 20 carbon atoms).Arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, containing one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having linear or branched chain alkyl radicals with 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, containing one or two phosphonic acid radicals), wherein the alkyl and aryl radicals may contain other substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

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

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

[057] The compounds of formula (I) are referred to herein as “active ingredients”. Petition 870250021756, dated 03 / 19 / 2025, p. 17 / 233 14 / 107

[058] In some embodiments, in the above formula (I), R1 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C8-cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, -C1-C6-alkyl-aryl, -C1-C6-alkyl-C1-C6-alkoxy, -Si(C1-Ce-alkyl)3, -SiAryl(C1-Ce-alkyl)2, -C(=O)Ra, -C(=O)N(Ra)2, -C1-C6-alkyl-OC(=O)Ra and -C1-C6-alkyl-C(=O)Ra, with Ra being selected from the group consisting of C1-C10-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, -C1C6-alkyl-C1-C6-alkoxy, C3-Cw-carbocyclyl, 3- to 10-membered heterocyclyl, aryl and heteroaryl, wherein R1 or Raacyclic and cyclic radicals may be substituted as described in this document.

[059] In some embodiments, in the above formula (I), R1 is selected from the group consisting of hydrogen, C1-Cw-alkyl, -Si(C1-C6-alkyl)3, C(=O)Rae - C1-C6-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. Acyclic and cyclic R1 or Ra radicals may be substituted as described in this document.

[060] In some embodiments, in the above formula (I), 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). Acyclic R1 or Ra radicals may be substituted as described in this document.

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

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

[063] In some embodiments, in the above formula (I), Cy is an 8, 9 or 10 membered bicyclic heteroaryl or an 8, 9 or 10 membered partially unsaturated bicyclic heterocyclyl, preferably a 9 or 10 membered bicyclic heteroaryl or a 9 or 10 membered partially unsaturated bicyclic heterocyclyl. Petition 870250021756, dated 03 / 19 / 2025, page 18 / 233 15 / 107

[064] Examples of 10-membered partially unsaturated heterocyclyl include 1,2,3,4-tetrahydroquinolin-1-yl, 1,2,3,4-tetrahydroquinolin-2-yl, 1,2,3,4tetrahydroquinolin-7-yl, 1,2,3,4-tetrahydroquinolin-8-yl, 1,2,3,4-tetrahydroisoquinolin-1-yl, 1,2,3,4-tetrahydroisoquinolin-2-yl, 1,2,3,4-tetrahydroisoquinolin-5-yl, 1,2,3,4tetrahydroisoquinolin-6-yl and 1,2,3,4-tetrahydroisoquinolin-7-yl.

[065] In some embodiments, in the above formula (I), Cy is a bicyclic Cw-aryl (e.g., naphthyl) or a partially saturated bicyclic C9-C10-carbocyclyl.

[066] There are no limits on what is included in the following items: A1 A2 A3 A4 A5 A6 A7 A8 A9 A10 A11 A12 A13 A14 A15 A16 A17 A18 A19 A20 A21 A22 A23 A24 A25 Petition 870250021756, on 03 / 19 / 2025, page. 19 / 233 16 / 107 A26 A29 A27 A28 N N A30 O N N A35 A31 A32 A33 A34 N N N A38 A39 N A36 A40 A37 A42 N O N O N N S A41 A43 A44 S A45 N n=n A56 A47 N A49 N A50 A54 A55 A58 A59 A60 N O A62 A63 A64 A65 A61 Petition 870250021756, on 03 / 19 / 2025, page. 20 / 233 17 / 107 A66 A67 A68 A69 A70 A72 A73 A74 A75 A71 A87 A89 A86 A88 A90 A92 A93 A94 A95 A91 Petition 870250021756, dated 03 / 19 / 2025, page 21 / 233 18 / 107 A98 A103 A106 A108 A109 A113 A114 A117 A126 A122 A127 A118 A119 A123 A128 A125 A130 Petition 870250021756, dated 03 / 19 / 2025, page 22 / 233 19 / 107 A131 A133 A134 A136 A138 A139 A141 A142 A143 A144 A145 A146 A147 A148

[067] In some embodiments, in the above formula (I), Cy is a 9- or 10-membered benzofused heteroaryl. Examples of 9-membered benzofused heteroaryl include indole-1-yl, indole-2-yl, indole-3-yl, indole-4-yl, indole-5-yl, indole-6-yl, indole-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-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-4yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl. Petition 870250021756, dated 03 / 19 / 2025, page 23 / 233 20 / 107

[068] Examples of 10-membered benzofused heteroaryl include 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.

[069] In some embodiments, in the above formula (I), Cy is selected from the group consisting of A1, A3, A9, A10, A48, A51, A56, A89 and A90 as disclosed in this document.

[070] In some embodiments, in the above formula (I), Cy is a 9-membered benzofused heteroaryl.

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

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

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

[074] Em algumas modalidades, na fórmula acima (I), R1 é um átomo de hidrogênio e X é um átomo de flúor ou um átomo de cloro.

[075] Em algumas modalidades, na fórmula acima (I), n representa 0, 1 ou 2.

[076] Em algumas modalidades, na fórmula acima (I), n representa 0 ou 1.

[077] Em algumas modalidades, na fórmula acima (I), n representa 0.

[078] 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-cyanoalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl, arylsulfanyl, C1-C6-alkylsulfinyl, arylsulfinyl, C1-C6-alkylsulfonyl, arylsulfonyl, C1-C6-alkylsulfonyl, arylsulfonyl, Ca-Cw-carbocyclyl, heterocyclyl from 3 to 10 members, aryl, heteroaryl, C3-C10-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, Petition 870250021756, dated 03 / 19 / 2025, page 24 / 233 21 / 107 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)R21, -N(R212)C(=NOR21)C(R21) -NR21C(=O)N(R21)2, NR21C(=O)R21, -NR21C(=S)R21, -NR21C(=S)N(R21)2, -NR21C(=NR21)R21, -OC(=O)R21, -OC(=O)N(R21)2, -OC(=O)R2 -S(=O)2R21, -S(=O)2N(R21)2, -O-C1-C6-(halo)alkyl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl, -C1-C6-(halo)alkyl-O-C3-C10-carbocyclyl -C1-C6-(halo)alkyl-heterocycle of 3 to 10 members, -C1-C6-(halo)alkyl-Oheterocycle of 3 to 10 members, -C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-heterocycle, -C1-C6-(halo)alkyl heteroaryl, -C1-C6-(halo)alkyl-heteroaryloxy, -C1-C6-(halo)alkyl-OR21, -C1-Ce(halo)alkyl-C(=O)R21, -C1-C6-(halo)alkyl-C(=O)OR21, -C1-Ce-(halo)alkyl-C(=O)OR21, -C1-Ce-(halo)alkyl-C(=O)R2 -C1-C6-(halo)alkyl-C(=O)N(OR21)R21, -C1-C6-(halo)alkylC(=O)NR21N(R21)2, -C1-C6-(halo)alkyl-C(=S)N(R21)2, -C1-C6-(halo)alkyl-C(=O)N(R21)2 -C1C6-(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(=O)R21)-C1-C6-(halo)alkylNR21C(=S)N(R21)2, -C1-C6-(halo)alkyl-OC(=O)R21, -C1-Ce-(halo)alkylOC(=O)N(R21)2, -C1-C6-(halo)alkyl-NR21S(=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)alkyl-S(=O)2OR21e -C1-C6-(halo)alkyl-S(=O)2N(R21)2 where R21 is as described herein, preferably, R21 is selected independently from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl, and C1-C6-(halo)alkyl-aryl. Acyclic R2 and R21 radicals and cyclic R2 and R21 radicals may be substituted as described in this document.

[079] 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-alkylsulfanyl (e.g., methylsulfanyl), C3-C10-carbocyclyl (preferably, C3-C6 Petition 870250021756, dated 03 / 19 / 2025, page 25 / 233 22 / 107 carbocyclil, p. 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-C6(halo)alkyl-aryl, -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 where R21 is as described in this document, preferably R21 is independently selected from the hydrogen-containing group, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl. Acyclic R2 and R21 radicals and cyclic R2 and R21 radicals may be substituted as described herein, preferably substituted by halogen or C1-C6(halo)alkyl.

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

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

[082] Examples of suitable -N(R21)2 radicals include -NH-C1-C6(halo)alkyl-aryl (preferably -NH-C1-C6-(halo)alkyl-phenyl, for example, -NH-CH2phenyl).

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

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

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

[086] Examples of suitable -C1-C6-(halo)alkyl-OR21 include -C1-C6(halo)alkyl-O-C1-C6-(halo)alkyl (e.g., methoxyethoxy). Petition 870250021756, dated 03 / 19 / 2025, p. 26 / 233 23 / 107

[087] Examples of suitable -Ci-C6-(halo)alkyl-C(=O)OR21 include Ci-Ce(halo)alkyl-C(=O)OH and Ci-Ce-(halo)alkyl-C(=O)-OCi-Ce-(halo)alkyl.

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

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

[090] In some embodiments (referred to in this document as embodiment Ia), the compounds of the present invention are compounds of formula (I)

[091] in which

[092] R1 is selected from the group consisting of hydrogen, C1-C8alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, -C1-C8-alkyl-aryl, -C1-C8alkyl-C1-C,-alkoxy -Si(C1-Ce-alkyl)3, -SiAryl(C1-Ce-alkyl)2, -C1-Ce-alkyl-C3-Cecycloalkyl, aryl, heteroaryl, -C1-C8-alkyl- heteroaryl, di-C1-C8-alkyl phosphate, C(=R -C1-Ce-alkyl-OC(=O)Rae -C1-Ce-alkyl-C(=O)Ra, with Rasendo selected from the group consisting of hydrogen, amino, C1-C10alkyl, C1-Ce-haloalkyl, C2-C8-alkenyl, C2-Cenyl, haloalkenyl C2-C8-alkynyl, C2C8-haloalkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylsulfanyl, C1-C8alkylamino, di-C1-C8-alkylamino, -C1-Ce-alkyl-C1-Ce-alkylamine, C C3C10-halocarbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, heterocyclyloxy, aryloxy and heteroaryloxyl,

[093] in which R1 or Raacyclic radicals can be replaced by one or more R1ae substituents in which R1 or Racyclic radicals can be replaced Petition 870250021756, dated 03 / 19 / 2025, p. 27 / 233 24 / 107 by one or more R1c substituents;

[094] m is 0 or 1;

[095] Cy is selected from the group consisting of A1 to A148 as revealed in this document;

[096] n is 0, 1 or 2, preferably 0 or 1;

[097] R2 is independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, CiC6-hydroxyalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy, C1-alkoxy, C C1-C6alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6alquinyl, C2-C6-haloalkynyla, C1-C6-alkylsulfanyl, arylsulfanyl, C1-C6-alkylsulfinyl, arylsulfinyl, C1-C6-alkylsulfonyl, arylsulfonyl, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, C3-C10-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, -C(O21)(O -C(=O)N(R21)2, C(=O)N(OR21)R21, -C(=O)NR21N(R21)2, -C(=S)N(R21)2, -C(=NOR21)R21, -N(R21)2, NR21C(=O)OR21, -NR21,R21(R21) -NR21C(=O)R21, -NR21C(=S)R21, NR21C(=S)N(R21)2, -NR21C(=NR21)R21, -OC(=O)R21, -OC(=O)N(R21)2, NR21S(=O)2R21, -NR21C(=R21, -S(=O)2N(R21)2, -O-C1-C6-(halo)alkyl-aryl, -C1-C6(halo)alkyl-C3-C10-carbocyclyl,-C1-C6-(halo)alkyl-O-C3-Cw-carbocyclyl -C1-C6(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-O-heterocyclyl of 3 to 10 members, -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, -C1C6-(halo)alkyl-C(=O)OR21, -C1-C6-(halo)alkyl-C(=O)N(R21)2, -C1-Ce-(halo)alkylC(=O)N(OR21)R21, -C1-C6-(halo)alkyl-C(=O)NR21N(R21)2, -C1-Ce-(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-Ce-(halo)alkylOC(=O)R21, -C1-C6-(halo)alkyl-OC(=O)N(R21)2, -C1-C6-(halo)alkyl-NR21S(=O)2R21, Petition 870250021756, dated 03 / 19 / 2025, p. 28 / 233, 25 / 107 C1-C6-(halo)alkyl-SR21, -Ci-C6-(halo)alkyl-S(=O)R21, -Ci-C6-(halo)alkyl-S(=O)OR21, -Ci-C6-(halo)alkyl-S(=O)2R21, -C1-C6-(halo)alkyl-S(=O)2OR21e -C1-Ce-(halo)alkylS(=O)2N(R21)2 where R21 is as described herein, preferably, R21 is selected independently from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl,

[098] wherein acyclic radicals R2 and R21 can be replaced by one or more substituents R22a and cyclic radicals R2 and R21 can be replaced by one or more substituents R22c, R22a and R22c as described in this document.

[099] In some embodiments (referred to in this document as embodiment Ib), the compounds of the present invention are compounds of formula (I) Cy (R2)n F— / o--N(F)m XF

[0100] in which

[0101] R1 is selected from the group consisting of hydrogen, C1-C6-alkyl, -Si(C1-Ce-alkyl)3, -C(=O)Rae -C1-C6-alkyl-C(=O)Ra, with Rasendo selected from the group consisting of C1-Cw-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-alkoxy, C3-Cw-carbocyclyl, aryl and heteroaryl,

[0102] where R1 or Raacyclic radicals can be replaced by one or more R1a substituents and where R1 or Racyclic radicals can be replaced by one or more R1c substituents; R1a and R1c being as disclosed in this document,

[0103] m is 0 or 1;

[0104] Cy is a heterosexual group of 8, 9 or 10 members;

[0105] X is a hydrogen, fluorine, or chlorine atom;

[0106] n is 0, 1 or 2, preferably 0 or 1; Petition 870250021756, dated 03 / 19 / 2025, p. 29 / 233 26 / 107

[0107] R2 is independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, CiC6-hydroxyalkyl, C1-C6-cyanoalkyl, C1-C6-alc C1-C6alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6alquinyl, C2-C6-haloalkynyla, C1-C6-alkylsulfanyl, arylsulfanyl, C1-C6-alkylsulfinyl, arylsulfinyl, C1-C6-alkylsulfonyl, arylsulfonyl, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, C3-C10-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, -C(O21)(O -C(=O)N(R21)2, C(=O)N(OR21)R21, -C(=O)NR21N(R21)2, -C(=S)N(R21)2, -C(=NOR21)R21, -N(R21)2, NR21C(=O)OR21, -NR21,R21(R21) -NR21C(=O)R21, -NR21C(=S)R21, NR21C(=S)N(R21)2, -NR21C(=NR21)R21, -OC(=O)R21, -OC(=O)N(R21)2, NR21S(=O)2R21, -NR21C(=R21, -S(=O)2N(R21)2, -O-C1-C6-(halo)alkyl-aryl, -C1-C6(halo)alkyl-C3-C10-carbocyclyl,-C1-C6-(halo)alkyl-O-C3-Cw-carbocyclyl -C1-C6(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-O-heterocyclyl of 3 to 10 members, -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, -C1C6-(halo)alkyl-C(=O)OR21, -C1-C6-(halo)alkyl-C(=O)N(R21)2, -C1-Ce-(halo)alkylC(=O)N(OR21)R21, -C1-C6-(halo)alkyl-C(=O)NR21N(R21)2, -C1-Ce-(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-Ce-(halo)alkylOC(=O)R21, -C1-C6-(halo)alkyl-OC(=O)N(R21)2, -C1-C6-(halo)alkyl-NR21S(=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)alkyl-S(=O)2OR21e -C1-Ce-(halo)alkylS(=O)2N(R21)2 wherein R21 is as described in this document, preferably R21 is selected independently from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, Petition 870250021756, dated 03 / 19 / 2025, p. 30 / 233 27 / 107

[0108] wherein acyclic radicals R2 and R21 may be replaced by one or more substituents R22a and cyclic radicals R2 and R21 may be replaced by one or more substituents R22c, R22a and R22c as described in this document.

[0109] Heteroarila of 8, 9 or 10 members (Cy) may be as described in this document.

[0110] In some embodiments (referred to in this document as embodiment Ic), the compounds of the present invention are compounds of formula (I) Cy (R2)n F- / oN(F)m XF

[0111] in which

[0112] 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),

[0113] in which R1 or Raacyclic radicals can be substituted as described in this document;

[0114] m is 0 or 1;

[0115] Cy selected from the group consisting of A1, A3, A9, A10, A48, A51, A56, A89 and A90;

[0116] X is a hydrogen, fluorine, or chlorine atom;

[0117] n is 0, 1 or 2, preferably 0 or 1;

[0118] 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-alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-alkylsulfanyl, arylsulfanyl, C1-C6-alkylsulfinyl, arylsulfinyl, C1-C6-alkylsulfonyl, arylsulfonyl, C3-C10-carbocyclyl, heterocyclyl Petition 870250021756, dated 03 / 19 / 2025, page 31 / 233 28 / 107 members, aryl, heteroaryl, C3-Cio-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, -C(=O)R21, -C(=O)OR21, -C(=O)N(R21)2, C(=O)N(R21)2, C(=O)N(21) -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)R21, -NR21C(=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, -C-O -C1-C6(halo)alkyl-C3-C10-carbocyclyl, -C1-C6-(halo)alkyl-O-C3-C10-carbocyclyl -C1-C6(halo)alkyl-heterocycle of 3 to 10 members, -C1-C6-(halo)alkyl-O-30-acyl members, -C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6(halo)alkyl-heteroaryloxy, -C1-C6-(halo)alkyl-OR21, -C1-C6-(halo)alkyl-O -C1C6-(halo)alkyl-C(=O)OR21, -C1-C6-(halo)alkyl-C(=O)N(R21)2, -C1-Ce-(halo)alkylC(=O)N(OR21)R21, -C1-C6-(halo)alkyl-C(=O)OR21, -C1-C6-(halo)alkyl-C(=O)N(R21) -C1-Ce-(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-Ce-(halo)alkylOC(=O)R21, -C1-C6-(halo)alkyl-OC(=O)N(R21)2, -C1-C6-(halo)alkyl-NR21S(=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)alkyl-S(=O)2OR21 and -C1-Ce-(halo)alkylS(=O)2N(R21)2 wherein R21 is as described in this document, preferably R21 is selected independently from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl,

[0119] wherein acyclic radicals R2 and R21 may be replaced by one or more substituents R22a and cyclic radicals R2 and R21 may be replaced by one or more substituents R22c, R22a and R22c as described in this document.

[0120] In some modalities according to modalities (Ia), (Ib) and (Ic), Cy is selected from the group consisting of A1, A3, A9, A10, A48, A51, A56, A89 and A90. Petition 870250021756, dated 03 / 19 / 2025, p. 32 / 233 29 / 107

[0121] In some modalities according to modalities (Ia), (Ib) and (Ic), Cy is selected from the group consisting of A1, A3, A9, A10, A51, A56, A89 and A90.

[0122] In some embodiments according to embodiments (Ia), (Ib) and (Ic), R1 is a hydrogen atom.

[0123] In some embodiments according to embodiments (Ia), (Ib) and (Ic), X is hydrogen.

[0124] In some modalities according to modalities (Ia), (Ib) and (Ic), X is fluorine.

[0125] In some forms according to forms (Ia), (Ib) and (Ic), X is chlorine.

[0126] In some embodiments according to embodiments (Ia), (Ib) and (Ic), R1 is a hydrogen atom and X is a chlorine atom.

[0127] In some embodiments according to embodiments (Ia), (Ib) and (Ic), R1 is a hydrogen atom and X is a fluorine atom.

[0128] In some modalities according to modalities (Ia), (Ib) and (Ic), n is 1.

[0129] In some modalities according to modalities (Ia), (Ib) and (Ic), n is 1 in is 0.

[0130] 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), diC1-C6-alkylamino, C1-C6-alkylsulfanyl, C3-C10-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-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-aryl, -C1-C6(halo)alkylheteroaryl, -C1-C6-(halo)alkyl-OR21and -C1-C6-(halo)alkyl-C(=O)OR21em Petition 870250021756, dated 03 / 19 / 2025, p. 33 / 233 30 / 107 where R21 is as described in this document, preferably R21 is selected independently 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 in this document, preferably substituted with halogen or C1-C6-(halo)alkyl.

[0131] In some embodiments according to embodiments (Ia), (Ib) and (Ic), X is F or Cl, R1 is hydrogen, m is 0 or 1, n is 0, and Cy is selected from the group consisting of A1, A3, A9, A10, A48, A51, A56, A89 and A90.

[0132] The present invention also relates to any compounds of formula (I) disclosed in Table 1.

[0133] The present invention relates to compounds of formula (I) selected from the group consisting of

[0134] 3-(4-quinazolin-2-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0135] 3-[4-(1-benzofuran-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0136] 3-[4-(1-benzothiophen-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0137] 3-[4-(1-benzofuran-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0138] 3-(4-pyrazolo[1,5-a]pyrimidin-3-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0139] 3-(4-pyrazolo[1,5-a]pyridin-3-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0140] 3-[4-(1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0141] 3-[2-fluoro-4-(1H-indol-6-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0142] 5-[chloro(difluoro)methyl]-3-[4-(1H-indol-6-yl)phenyl]-4H-1,2-oxazol-5-ol,

[0143] 3-[3-fluoro-4-(1H-indol-6-yl)phenyl]-4H-1,2-oxazol-5-ol H-indol-6-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,

[0144] 3-(4-imidazo[1,2-a]pyrimidin-6-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol e

[0145] 3-[4-([1,3]thiazolo[4,5-c]pyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol. Petition 870250021756, dated 03 / 19 / 2025, page 34 / 233 31 / 107

[0146] The compounds of formula (I) according to the present invention can be used as fungicides (i.e., to control phytopathogenic fungi, in particular fungi that cause rust diseases, or Oomycetes in the protection of agricultural crops). PROCESSES FOR PREPARING COMPOUNDS OF FORMULA 1

[0147] The compounds of formula (I) can be prepared according to processes described in document no. WO2008 / 006561 and document no. WO 2019 / 122393.

[0148] The following table lists the abbreviations used in this paragraph and in the 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 DMAP N,N-dimethylaminopyridine DMF N,N-dimethylformamide 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 liquid chromatography / mass spectrometry Petition 870250021756, dated 03 / 19 / 2025, page 35 / 233 32 / 107 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 cyclic anhydride of 1-propanesulfonic acid TEA: Triethylamine TFA: Trifluoroacetic acid THF: Tetrahydrofuran

[0149] It is understood that, when in aqueous medium, compounds of formula (I') in which R1 is hydrogen and R2, X, m, ne Cy are as defined above, may be present in a reversible equilibrium with the corresponding open form (or General synthetic routes for compounds of general formula I

[0150] The present invention also relates to processes for the preparation of compounds of formula (I). Except where 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.

[0151] Compounds of the formula (Γ), where R1 = H, can be prepared, Petition 870250021756, dated 03 / 19 / 2025, p. 36 / 233 33 / 107 according to process P1, by the reaction of 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 similar to ethanol (as described, for example, in Journal of Heterocyclic Chemistry, 2010, 47(6), 1310-1316). X F Cy m OO R2)n (I') (II) Process P1

[0152] The diketones of formula (II) can be prepared according to known procedures (see, for example, document no. WO2008006561), as shown in process P2 by treating ketones of formula (III) with a suitable base, preferably in a solvent (for example, sodium ethoxide in ethanol or sodium hydride in THF), followed by the addition of a fluoroacetyl electrophile, for example, ethyl trifluoroacetate. (cy)CCyy | || ^(R2)n-----------X\l JL\J1 (R2)n O ( F)m OO(F)m (III) (II) P2 Process

[0153] It is understood that the intermediates of formula (II) according to Petition 870250021756, dated 03 / 19 / 2025, p. 37 / 233 34 / 107 invention, wherein X, R2, m, ne Het are as defined above, may be present as the diketone (as represented in Process 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.

[0154] The compounds of formula (III) may be commercially available or may be prepared from readily available compounds according to known procedures.

[0155] The compounds of formula (I) can be prepared, according to process P3, by reacting compounds of formula (I'), wherein R1 = H, with an electrophile of formula (IV), wherein LG1 is a leaving 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 of Heterocyclic Chemistry, 2005, 42(7), 1253-1255). Process P3 LG1—R1 (IV) (0

[0156] The compounds of formula (IV) may be commercially available or may be prepared from readily available compounds according to known procedures.

[0157] Alternatively, compounds of formula (I) can be prepared, according to process P4, from a compound of formula (V), wherein W1 is a leaving group such as, for example, bromine, by cross-coupling reaction with a compound of formula (VI), wherein M1 is a metal or a metalloid (for example -B(OH)2 or -ZnCl) in the presence of a base (such as, for example, Petition 870250021756, dated 03 / 19 / 2025, p. 38 / 233 35 / 107 cesium carbonate) and a catalyst (such as, for example, Tetrakis(triphenylphosphine)palladium (0) ) in a solvent such as, for example, dioxane and water. W1 R1—O (V) x F (0 Process P4

[0158] The compounds of formula (V) can be prepared from readily available compounds analogously to processes P1 and P2.

[0159] 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.

[0160] Alternatively, compounds of formula (I) can be prepared, according to process P5, from a compound of formula (VII), wherein M2 is a metal or a metalloid (for example -B(OH)2 or -ZnCl), by cross-coupling reaction with a compound of formula (VIII), wherein W2 is a leaving group such as, for example, bromine in the presence of a base (such as, for example, cesium carbonate) and a catalyst (such as, for example, Tetrakis(triphenylphosphine)palladium (0) ) in a solvent such as, for example, dioxane and water. Petition 870250021756, dated 03 / 19 / 2025, p. 39 / 233 36 / 107

[0161] The compounds available or may be (0 of formula (VIII) can be commercially prepared from readily available compounds according to known procedures.

[0162] The compounds of formula (VII) can be prepared, according to process P6, from compounds of formula (V), wherein W1 is a leaving group, such as bromine, for example, by metal-halogen exchange or by palladium-catalyzed borylation. Processes P6 and P5 can be combined into a 'one-pot' process. M2 R1~O (V) Process P6 W1 F (VII) R1~o

[0163] According to the invention, processes P1 to P6 can be carried out, if suitable, in the presence of a solvent and, if suitable, in the presence of a base.

[0164] The solvents suitable for carrying out processes P1 to P6 according to the invention are ordinary inert organic solvents. Preference is given to the use of aliphatic, alicyclic or aromatic hydrocarbons. Petition 870250021756, dated 03 / 19 / 2025, page 40 / 233 37 / 107 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.

[0165] The suitable bases for carrying out processes P1 to P6 according to the invention are inorganic and organic bases that are customary 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-diaza-bicyclo[5.4.0]undec-7ene (DBU).

[0166] When carrying out processes P1 to P6, according to the invention, the reaction temperature can vary independently within a relatively wide range. In general, the processes according to the invention are carried out at temperatures between -20°C and 160°C. Petition 870250021756, dated 03 / 19 / 2025, page 41 / 233 38 / 107

[0167] Processes P1 to P6 according to the invention are generally carried out independently under atmospheric pressure. However, it is also possible to operate under high or low pressure.

[0168] The work is carried out by customary methods. In general, 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 customary methods, such as chromatography or recrystallization, from any impurities that may still be present.

[0169] 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. Compositions and formulations

[0170] The present invention further relates to a composition, in particular a composition for controlling unwanted microorganisms, comprising one or more compounds of formula (I). The composition is preferably a fungicidal composition.

[0171] 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.

[0172] A carrier is a solid or liquid substance, natural or synthetic, organic or inorganic, that is generally inert. The carrier generally enhances the application of compounds, for example, to plants, plant parts, or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural rock flours such as kaolin, clays, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, and synthetic rock flours such as Petition 870250021756, dated 03 / 19 / 2025, page 42 / 233 39 / 107 Finely divided silica, alumina, and silicates. Examples of typically useful solid carriers 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 stems. 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 dimethyl sulfoxide).The carrier may also be a liquefied gaseous extender, i.e., 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 carrier 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.

[0173] The composition may additionally comprise one or more acceptable excipients that are customary for formulating compositions (e.g., agrochemical compositions), such as one or more surfactants.

[0174] The surfactant can be an ionic surfactant (cationic or anionic) or Petition 870250021756, dated 03 / 19 / 2025, page 43 / 233 40 / 107 non-ionic surfactant, as an ionic or non-ionic emulsifier (or emulsifiers), foam former (or foam formers), dispersant (or dispersants), wetting agent (or wetting agents) and any mixtures thereof.Examples of suitable surfactants include, but are not limited to, polyacrylic acid salts, lignosulfonic acid salts, phenolsulfonic acid or naphthalenesulfonic acid salts, polycondensates of ethylene and / or propylene oxide 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, alkylsulfonates, alkylsulfates, arylsulfonates) and protein hydrolysates. Lignosulfonate and methylcellulose residue liquors.A surfactant is typically used when the compound of formula (I) and / or the carrier is insoluble in water and the application is made with water. Then, the amount of surfactant typically ranges from 5 to 40% by weight of the composition.

[0175] Additional examples of auxiliaries that are customary for formulating 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, photostabilizers or other agents that improve chemical and / or physical stability), colorants or pigments (such as inorganic pigments, e.g., iron oxide, titanium oxide and blue of Petition 870250021756, dated 03 / 19 / 2025, page 44 / 233 41 / 107 Prussia; organic dyes, e.g., alizarin, azo dyes and metal phthalocyanine), antifoaming agents (e.g., silicone antifoaming agents and magnesium stearate), preservatives (e.g., 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.

[0176] 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 specific properties (technical, physical and / or biological properties) to the compositions or forms of use prepared from them. The choice of auxiliaries may allow the customization of the compositions for specific needs.

[0177] The composition may be in any customary form, such as solutions (e.g., aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, 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.

[0178] The composition may be supplied to the end user as a ready-to-use formulation, i.e., the compositions may be directly applied to plants or seeds by a suitable device, such as a sprayer or spraying device. Alternatively, the composition may be supplied to the end user in the form of concentrates that must be diluted, preferably with water, Petition 870250021756, dated 03 / 19 / 2025, page 45 / 233 42 / 107 before use.

[0179] The composition can be prepared in a conventional manner, for example, by mixing the compound of formula (I) with one or more suitable auxiliaries, as disclosed in the present document above.

[0180] 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, most preferably from 1 to 80% by weight of the compound of formula (I).

[0181] The compound (or compounds) and composition (or compositions) comprising them may be mixed with other active ingredients such as fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, protectants or semiochemical agents. This may allow for broadening the spectrum of activity or preventing the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in the Pesticide Manual, 17th Edition.

[0182] Examples of fungicides that could be mixed with the compound (or compounds) of formula (I) and the composition of the invention are:

[0183] 1) Inhibitors of ergosterol biosynthesis, for example, (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) phenexamide, (1.005) phenpropidine, (1.006) phenpropimorph, (1.007) phenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalyl, (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)-2methyl-1 -(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)2-(chloromethyl)-2-methyl-1 -(1H-1,2,4-triazol-1 -ylmethyl)cyclopentanol, (1.028) (2R)-2-(1 Petition 870250021756, dated 03 / 19 / 2025, page 46 / 233 43 / 107 chlorocyclopropyl)-4-[(1 R)-2,2-dichlorocyclopropyl]-1 -(1 H-1,2,4-triazol-l -yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1 S2,2)- H-1,2,4-triazol-l 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)-2,2dichlorocyclopropyl]-1 -(1 H-1,2,4-triazol-1 -yl)butan-2-ol, (1.032) (2S)-2-(1 -chlorocyclopropyl)-4-[(1-2-S -(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)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3yl)methanol, (1.035) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol4-yl](pyridin-3-yl)methanol, (1037) 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 -({(2C,4S)-2-[2-chloro-4-(4chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1 H-1,2,4-triazole, (1.039) 1 -{[3-(2chlorophenyl)-2-(2,4-difluoro-oxymethylranyl)-2-1) H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.04) -{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy2,6,6-trimethyleptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3-thione, (1,043) 2-[(2R,4R,5S)-1 (2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyleptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3thione, (1.044) 2-[(2R,4S,5R)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]2,4-di-hydro-3H-1,2,4-triazole-3-thione, (1045) 2-[(2R,4S,5S)-1 -(2,4-dichloro-phenyl)-5hydroxy-2,6,6-trimethyleptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3-thiona, (1.046) 2[(2C,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyleptane-4-yl]-2,4-di-hydro-3H1,2,4-triazole-3-thiona, (1.047) 2-[(2C,4R,5C)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3-thiona, (1,048) 2-[(2S,4S,5R)-1 -(2,4dichlorophenyl)-5-hydroxy-2,6,6-trimethyleptane-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyleptan-4-yl]-2,4-diPetition 870250021756, of 19 / 03 / 2025, p. 47 / 233. 44 / 107 hydro-3H-1,2,4-triazole-3-thion, (1,050) 2-[1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6trimethyleptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazol-3-thion, (1,051) 2-[2-chloro-4-(2,4dichlorophenoxy)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4chlorophenoxy)phenyl]-1 -(1 H-1,2,4-triazol-2-ylbutan), (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)phenyl -1-(1,1-1)-triazol, -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-1,2,4triazole-3-thion, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluoro-phenyl)oxiran-2yl]methyl}-2,4-di-hydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1.059) 5-(4chlorobenzyl)-2-(chloromethyl-1)-(1-1) H-1,2,4-triazol-1 -ylmethyl)cyclopentanol, (1060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1 -{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N'-(2,5dimethyl-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-Nmethylimidoformamide, (1.066) N'-(2,5-dimethyl-4-{[3(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N'-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-Nmethylimidoformamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.068)069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N'-(2,5-dimethyl-4-{3[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1,071) N'-(2,5dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1,072) N'-(4-{[3(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1,073). Petition 870250021756, dated 03 / 19 / 2025, p. 48 / 233 45 / 107 N'-(4-{3-[(difluoro-methyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1,074) N'-[5-bromo-6-(2,3-di-hydro-1 H-inden-2-iloxy)-2-methylpyridine-3-yl]-N-ethyl-Nmethylimido-formamide, (1,075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-Nethylform-1limi N-da6,meti N'-{5-bromo-6-[(1 R)-1 -(3,5-difluorophenyl)ethoxy]-2methylpyridine-3-yl}-N-ethyl-N-methylimido-formamide, (1,077) N'-{5-bromo-6-[(1S)-1-(3,5difluorophenyl)ethoxy]-2-methylpyridine-3-yl}-N-ethyl-N-methylimido-formamide, (1.078) N'-{5bromo-6-[(cis-4-isopropyl-cyclohexyl)oxy]-2-methylpyridine-3-yl}-N-ethyl-Nmethylimidoformamide, (1,079) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2methylpyridine-3-yl}-N-ethyl-N-methylimidoformamide, (1,080) N'-{5-bromo-6-[1 -(3,5-difluorophenyl)ethoxy]-2-methylpyridine-3-yl}-N-ethyl-N-methylimido-formamide, (1,081) ipfentrifluconazole, (1,082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)-(trifluoromethyl) H-1,2,4triazol-1 -yl)propane-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-hydroxy-propyl]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-1hydroxy-1-phenylethyl)phenyl]-N-methylimidoformamide, (1.088) N'-{5-bromo-2-methyl-6-[(1propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimido-formamide, (1.089) hexaconazole, (1.090) penconazole, (1.091) fenbuconazole and (1.092) methyl 2-[2-chloro-4(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoato.

[0184] 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) fluxapyroxad, (2.008) furomethpyr, (2.009) isofetamid, (2.010) isopyrazam (antiepimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (antiepimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (antiepimeric racemate 1RS,4SR,9SR), (2.013) isopyrazam (racemate mixture) synepimeric Petition 870250021756, dated 03 / 19 / 2025, p. 49 / 233 46 / 107 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (synepimeric enantiomer 1R,4S,9R), (2.015) isopyrazam (synepimeric enantiomer 1S,4R,9S), (2.016) isopyrazam sinepimeric 1RS,4SR,9RS), (2,017) penflufen, (2,018) pentiopyrate, (2,019) pidiflumethofen, (2,020) Pyraziflumide, (2,021) sedaxano, (2,022) 1,3-dimethyl-N-(1,1,3-trimethyl-3-hydro H-inden-4-yl)-1 H-pyrazole4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-di-hydro-1 H-inden-4-yl]1 H-pyrazol-4-carboxamide, (2.024) 1,3-methyl-N-C-(3,023)[ 1,3-trimethyl-2,3-di-hydro-1 Hinden-4-yl]-1 H-pyrazol-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'(trifluoromethyl)biphenyl-2-yl]-1 H-pyrazol-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)N-(1, 1,3-trimethyl-2,3-di-hydro-1 H-inden-4-yl)benzamide, (2,027) 3-(difluoromethyl)-1 methyl-N-(1,1,3-trimethyl-2,3-di-hydro-1-inden-4-yl-1) H-pyrazole-4-carboxamide, (2,028) inpirfluxam, (2.029) 3-(difluoromethyl)-1 -methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 Hinden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) fluindapir, (2.031) 3-(difluoromethyl)-N[(3R)-7-fluoro-1, 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1Hinden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4(trifluoromethyl)-pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) isoflucipram, (2.039) N-[(1R,4S)-9-(diclorometileno)-1,2,3,4-tetraidro-1,4metanonaftalen-5-il]-3-(difluorometil)-1-metil-1H-pirazol-4-carboxamida, (2.040) N[(1 S,4R)-9-(diclorometileno)-1,2,3,4-tetraidro-1,4-methanonaftalen-5-il]-3(difluorometil)-1 -metil-1 H-pirazol-4-carboxamida, (2.041) N-[1 -(2,4-diclorofenil)-1 metoxipropan-2-il]-3-(difluorometil)-1-metil-1 H-pirazol-4-carboxamida, (2.042) N-[2Petição 870250021756, de 19 / 03 / 2025, pág. 50 / 233. 47 / 107 cloro-6-(trifluorometil)benzil]-N-ciclopropil-3-(difluorometil)-5-fluoro-1-metil-1H-pirazol4-carboxamida, (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-isopropylbenzil)-1-metil-1 H-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-carbotioamida, (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.

[0185] 3) Respiratory chain inhibitors in complex III, for example, (3.001) ametoctradine, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumoxystrobin, (3.005) coumoxystrobin, (3.006) ciazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, Petition 870250021756, dated 03 / 19 / 2025, page 51 / 233 48 / 107 (3.011) flufenoxistrobina, (3.012) fluoxastrobina, (3.013) cresoxim-metila, (3.014) metominostrobina, (3.015) orisastrobina, (3.016) picoxistrobina, (3.017) piraclostrobina, (3.018) pirametostrobina, (3.019) piraoxistrobina, (3.020) trifloxystrobina, (3.021) (2E)-2-{2-[({[(1 E)-1 -(3-{[(E)-1 -fluoro-2fenilvinil]oxi}fenil)ethylideno]amino}oxi)metil]fenil}-2-(methoxyimino)-N-methylacetamida, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1 H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3 dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5 trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1 -(4-chloro-2 fluorophenyl)-1 H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) {5[3-(2,4-dimethylfenil)-1H-pyrazol-1-yl]-2-metilbenzil}carbamato de methyla, metiltetraprol, (3.031) florylpicoxamide.

[0186] 4) Inhibitors of mitosis and cell division, for example, carbendazim, (4.002) dietofencarb, (4.003) etaboxam, (4.004) fluopicolide, (3.030) (4.001) (4.005) pencicuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridaclomethyl, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,014) 4-(2-bromo-4-fluorophenyl)-N-(2bromophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,015) 4-(2-bromo-4-fluorophenyl)-N-(2chloro-6-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,016) 4-(2-bromo-4-fluorophenyl)N-(2-chlorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,017) 4-(2-Bromo-4-fluorophenyl)-N(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4,018) 4-(2-chloro-4-fluorophenyl)-N-(2,6 difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4,019) 4-(2-chloro-4-fluorophenyl)-N-(2 chloro-6-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,020) 4-(2-chloro-4-fluorophenyl)-NPection 870250021756, de 19 / 03 / 2025, p. 52 / 2 49 / 107 (2-chlorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,021) 4-(2-chloro-4-fluorophenyl)-N-(2fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4,022); 4-(4-chlorophenyl)-5-(2,6difluorophenyl)-3,6-dimethylpyridazine, (4,023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.026) fluopimomide.

[0187] 5) Compounds capable of having a multi-site action, for example, (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianone, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) zinc metiram, (5.017) copper oxin, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3c][1,2]thiazol-3-carbonitrile.

[0188] 6) Compounds capable of inducing a host defense, for example, (6.001) acibenzolar-S-methyl, (6.002) isothianyl, (6.003) probenazole, (6.004) thiadyl.

[0189] 7) Inhibitors of amino acid and / or protein biosynthesis, for example, (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline

[0190] 8) Inhibitors of ATP production, for example, (8.001) silthiofam.

[0191] 9) Cell wall synthesis inhibitors, for example, (9.001) bentiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) Petition 870250021756, dated 03 / 19 / 2025, page 53 / 233 50 / 107 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-(4tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0192] 10) Lipid and membrane synthesis inhibitors, for example, (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofosmethyl.

[0193] 11) Inhibitors of melanin biosynthesis, for example, (11.001) tricyclazole, (11.002) tolprocarb.

[0194] 12) Nucleic acid synthesis inhibitors, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (chiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0195] 13) Signal transduction inhibitors, for example, (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxifene, (13.006) vinclozoline.

[0196] 14) Compounds capable of acting as an uncoupler, for example, (14.001) fluazinam, (14.002) meptildinocap.

[0197] 15) Additional 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) quinomethionate, (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 dimethyldithiocarbamate, (15.020) isopropyl nitrothalamic acid, (15.021) oxamocarb, (15.022) oxathiapiproline, (15.023) oxyfenthiamine, (15.024) pentachlorophenol and 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-dihydro-1,2Petition 870250021756, dated 03 / 19 / 2025, page 54 / 233 51 / 107 oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-metil-3-(trifluorometil)-1H-pyrazol-1 yl]ethanone, (15.032) 1 -(4-{4-[(5S)-5-(2,6-difluorofenil)-4,5-di-hidro-1,2-oxazol-3-yl]-1,3thiazol-2-yl}piperidin-1 -yl)-2-[5-metil-3-(trifluorometil)-1 H-pyrazol-1 -yl]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) dipimetitron, (15.035) 2-[3,5bis(difluorometil)-1H-pyrazol-1-yl]-1 -[4-(4-{5-[2-(prop-2-in-1 -yloxy)fenil]-4,5-di-hidro-1,2oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1 -yl]ethanone, (15,036) 2-[3,5-bis(difluoromethyl)-1-yl]-1-yl]pyrazol-1-yl] -[4-(4-{5-[2-cloro-6-(prop-2-in-1 -iloxi)fenil]-4,5-di-hidro-1,2-oxazol-3-yl}1,3-thiazol-2-yl)piperidin-1 -yl]ethanona, (15,037) 2-[3,5-bis(difluoromethyl)-1-yl]-1-pyrazol-1-yl] -[4-(4-{5-[2-fluoro-6-(prop-2-in-1 -yloxy)-phenyl]-4,5-di-hydro-1,2-oxazol-3-yl}-1,3-thiazol2-yl)piperidin-1 -yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[[3,5-bis(difluoro-methyl)-1 H-pyrazol-1 yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-di-hydro-1,2-nossu-oxazol-methazol-3-5 (15,040) methanosulfonate of 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)1 H-pyrazol-1 -yl]acetyl}piperidine-4-yl)-1,3-thiazol-4-yl]-4,5-zol-35-di-hydroxyl}-1 (15,041) ipflufenoquine, (15,042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3yl)oxy]phenyl}propan-2-ol, (15,043) fluoxapiproline, (15,044) methanosulfonate 2-{3[2-(1-{[[3,5-bis(difluoromethyl))-1 H-pyrazol-1-yl]acetyl}piperidine-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl, (15.04,465) 3-(4,4,5-trifluoro-3,3dimethyl-3,4-di-hydroisoquinolin-1-yl)quinoline, (15,047) quinofumelin, (15,048) 4amino-5-fluoropyrimidine-2-ol (tautomeric formH:-4(1-amino-pyrimine)-4(1-amino-pyrimine) (15,049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15,050) 5-amino-1,3,4thiadiazol-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-in-1 -yl)thiophene-2-sulfonohydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxi]-pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4methylbenzyl)oxi]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) {6-[({[(Z)-(1-methyl-1 H-tetrazol-5yl)(phenyl)methyleno]amino}oxi)methyl]pyridin-2-yl}carbamate de but-3-in-1-yl, (15.056) (2Z)3-amino-2-cyano-3-ethyl phenylacrylate, (15.057) phenazine-1-carboxylic acid,. Petition 870250021756, 19 / 03 / 2025, pág. 55 / 233 52 / 107 (15.058) 3,4,5-trihydroxybenzoate propyl, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) {6-[({[(1-methyl-1H-tetrazol-5yl)(phenyl)methyleno]amino}oxy)methyl]pyridin-2-yl}carbamate tert-butyl, (15.062) 5fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-di-hydropyrimidin-2(1 H)-one, (15.063) aminopyrifen, (15.064) (N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimido-formamida), (15.065) (N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimido-formamida), (15.066) (2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxi]-6-fluorophenyl}propan2-ol), (15.067) (5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068) (3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline), (15,069) (1-(4,5-dimethyl-1 H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihidroisoquinoline), (15,070) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-di-hidroisoquinolin-1 yl)quinolone, (15.071) 8-fluoro-3-(5-fluoro-3,3,4,4-tetrametil-3,4-di-hidroisoquinolin-1il)quinolona, (15.072) 3-(4,4-difluoro-3,3-dimetil-3,4-di-hidroisoquinolin-1 -il)-8fluoroquinolina, (15.073) (N-metil-N-fenil-4-[5-(trifluorometil)-1,2,4-oxadiazol-3il]benzamida), (15.074) {4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil}carbamato de metila, (15.075) (N-{4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzil}-ciclopropanocarboxamida), (15.076) N-metil-4-(5-(trifluorometil)-1,2,4-oxadiazol-3-il]-benzamida, (15.077) N-[(E)-metoxiimino-metil]-4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.078) N-[(Z)-metoxiiminometil]-4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.079) N-[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]-cyclopropane-carboxamida, (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-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15.083) N-[(E)-N-methoxy-C-methyl-carbonimidoyl]-4-(5-(trifluoro-methyl)-1,2,4-oxadiazol-3-yl)-benzamide, (15.084) N-[(Z)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)1,2,4-oxadiazol-3-yl]benzamide, (15.085) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]-methyl]-propanamide, (15.086) 4,4-dimethyl-1 -[[4-[5-(trifluoromethyl)Petição 870250021756, from 19 / 03 / 2025, pág. 56 / 233. 53 / 107 1,2,4-oxadiazol-3-yl]phenyl]methyl]-pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl) 1,2,4-oxadiazol-3-yl]-benzenocarbotioamida, (15.088) 5-metil-1 -[[4-[5-(trifluorometil)1,2,4-oxadiazol-3-yl]fenil]metil]pyrrolidin-2-ona, (15.089) N-((2,3-difluoro-4-[5(trifluorometil)-1,2,4-oxadiazol-3-yl]fenil]metil]-3,3,3-trifluoro-propanamida, (15.090) 1metoxi-1-metil-3-[[4-[5-(trifluoro-metil}-1,2,4-oxadiazol-3-yl]fenil]-metil)urea, (15.091) 1, 1 -diethyl-3-[[4-[5-(trifluorometil}-1,2,4-oxadiazol-3-yl]fenil]metil]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) 1 -methoxy-3-methyl-1 -[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-methyl)-cyclopropanecarboxamide, (15.096) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]-propanamide, (15.098) 1 -methoxy-3-methyl-1 -[[4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]-methyl]-urea, (15.099) 1,3-dimethoxy-1 -[[4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]methyl]urea, (15.100) 3-ethyl-1 -methoxy-1 -[[4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]methyl]urea, (15.101) 1 -[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-yl]fenil]-metil]piperidin-2-one, (15.102) 4,4-dimethyl-2-[[4-[5-(trifluorometil)-1,2,4oxadiazol-3-yl]fenil]-metil]isooxazolidin-3-one, (15.103) 5,5-dimethyl-2-[[4-[5(trifluorometil)-1,2,4-oxadiazol-3-yl]fenil]metil]isoxazolidin-3-ona, (15.104) 3,3-dimethyl1 -[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-yl]-fenil]-metil]-piperidin-2-one, (15.105) 1 -[[3fluoro-4-(5-(trifluorometil)-1,2,4-oxadiazol-3-yl]-fenil]-metil]-azepan-2-ona, (15.106) 4,4-dimethyl-2-[[4-(5-(trifluorometil)-1,2,4-oxadiazol-3-yl]-fenil]-metil]isoxazolidin-3-one, (15.106)107) 5,5-dimetil-2-[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]isoxazolidin-3-ona, (15.108) 1 -{4-[5-(trifluorometil)-1,2,4-oxadiazol-3il]benzil}-1H-pirazol-4-carboxilato de etila, (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-{2,3-difluoro-4-[5(trifluorometil)-1,2,4-oxadiazol-3-il]benzil}butanamida, (15.111) N-(1 -metilciclopropil)Petição 870250021756, de 19 / 03 / 2025, pág. 57 / 233. 54 / 107 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamida, (15.112) N-(2,4-difluorophenyl)-4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamida, (15.113) 1 -(5,6-dimethylpyridin-3-yl)-4,4difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114) 1 -(6-(difluoromethyl)-5-methylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydro-isoquinoline, (15.115) 1 -(5(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116) 1 -(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.117) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl dimethylcarbamate, (15.118) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propanamide, (15.119) methanesulfonate 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-di-hidro-2,4-benzodioxepin-6-yl, (15.120) methanesulfonate de 9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-di-hidro-2,4-benzodioxepin-6-yl, (15.121) methanesulfonate de 3-[2-(1 -{[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4yl)-1,3-thiazol-4-yl]-1,5-di-hidro-2,4-benzodioxepin-6-yl, (15.122) methanesulfonate de 3-[2-(1 -{[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9fluoro-1,5-di-hidro-2,4-benzodioxepin-6-yl, (15.123) 1 -(6,7-dimethylpyrazolo[1,5a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-di-hidroisoquinolina, (15.124) 8-fluoro-N(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinolina-3-carboxamida, (15.125) 8-fluoro-N[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinolina-3-carboxamida, (15.126) N(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamida and (15,127) N-[(2S)2,4-dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamida.

[0198] All named mixing partners of classes (1) to (15), as described above, may be present in the form of the free compound and / or, if their functional groups permit, an agriculturally acceptable salt thereof.

[0199] The compounds of formula (I) and compositions comprising them may be combined with a biological control agent.

[0200] Examples of biological control agents that can be Petition 870250021756, dated 03 / 19 / 2025, p. 58 / 233 55 / 107 combined with the compounds of formula (I) and compositions comprising them are:

[0201] (A) Selected antibacterial agents from the group of:

[0202] (A1) bacteria, such as (A1.1) Bacillus subtilis, in particular the QST713 / AQ713 strain (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, with Accession Number NRRL B21661 and described in US Patent No. 6,060,051); (A1.2) Bacillus amyloliquefaciens, in particular the D747 strain (available as Double Nickel™ from Certis, US, with Accession Number FERM BP-8234 and disclosed in US Patent No. 7,094,592); (A1.3) Bacillus pumilus, in particular the BU F-33 strain (with Accession Number NRRL 50185); (A1.4) Bacillus subtilis var. amyloliquefaciens FZB24 (available as Taegro® from Novozymes, US); (A1.5) a Paenibacillus sp. strain with NRRL Accession No. B-50972 or NRRL Accession No. B-67129 and described in International Patent Publication No. WO 2016 / 154297; and

[0203] (A2) fungi, such as (A2. 1) Aureobasidium pullulans, in particular blastospores of strain DSM14940; (A2. 2) Aureobasidium pullulans blastospores from strain DSM 14941; (A2. 3) Aureobasidium pullulans, in particular mixtures of blastospores from strains DSM14940 and DSM14941;

[0204] (B) Selected fungicides from the group of:

[0205] (B1) bacteria, for example, (B1.1) Bacillus subtilis, in particular a QST713 / AQ713 strain (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, with 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® from Bayer CropScience LP, US, with NRRL Accession No. B30087 and described in US Patent No. 6,245,551); (B1.3) Bacillus pumilus, in particular the GB34 strain (available as Yield Shield® from Bayer AG, DE); (B1.4) Bacillus pumilus, in particular the BU F-33 strain (with Accession Number NRRL 50185); (B1.5) Petition 870250021756, dated 03 / 19 / 2025, p. 59 / 233 56 / 107 Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ from Certis, US, with accession number FERM BP-8234 and disclosed in US Patent No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277); (B1.7) strain Bacillus amyloliquefaciens MBI 600 (available as SUBTILEX from BASF SE); (B1.8) strain Bacillus subtilis GB03 (available as Kodiak® from Bayer AG, DE); (B1.9) strain Bacillus subtilis var. 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 No. 70127-5); (B1. 10) Bacillus mycoides, isolate J (available as BmJ TGAI or WG from Certis USA); (B1.11) Bacillus licheniformis, in particular strain SB3086 (available as EcoGuard™ Biofungicide and Green Releaf alongside Novozymes); (B1.12) a Paenibacillus sp. strain with NRRL Accession No. B-50972 or NRRL Accession No. B-67129 and described in International Patent Publication No. WO 2016 / 154297.

[0206] In some embodiments, the biological control agent is a Bacillus subtilis or Bacillus amyloliquefaciens strain that produces a fengicin or plipastatin-like compound, an iturin-like compound, and / or a surfactin-like compound. For more 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, pages 115-125. Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, with Accession Number NRRL B21661 and described in US Patent No. 6,060,051), and Bacillus amyloliquefaciens strain D747 (available as Double Nickel™ from Certis, US, with Accession Number FERM BP-8234 and disclosed in US Patent No. Petition 870250021756, dated 03 / 19 / 2025, p. 60 / 233 57 / 107 7,094,592); Bacillus subtilis MBI600 (available as SUBTILEX® from Becker Underwood, US No. Reg. EPA 71840-8); Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277); Bacillus amyloliquefaciens, in particular the strain FZB42 (available as RHIZOVITAL® from ABiTEP, DE); and Bacillus subtilis var. 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 No. 70127-5); and

[0207] (B2) fungi, for example: (B2. 1) Coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660; e.g., Contans ® from Bayer); (B2. 2) Metschnikowia fructicola, in particular strain NRRL Y-30752 (e.g. Shemer®); (B2. 3) Microsphaeropsis ochracea (e.g., Microx® next to Prophyta); (B2. 5) Trichoderma spp., including Trichoderma atroviride, the SC1 strain described in International Application No. PCT / IT2008 / 000196); (B2.6) Trichoderma harzianum rifai KRL-AG2 strain (also known as T-22 strain, / ATCC 208479, e.g., PLANTSHIELD T-22G, Rootshield®, and TurfShield near BioWorks, US); (B2.14) Gliocladium roseum, strain 321U near WF Stoneman Company LLC; (B2.35) Talaromyces flavus, strain V117b; (B2.36) Trichoderma asperellum, strain ICC 012 near Isagro; (B2.37) Trichoderma asperellum, strain SKT-1 (e.g., ECO-HOPE® near Kumiai Chemical Industry); (B2. 38) Trichoderma atroviride, strain CNCM I1237 (e.g., Esquive® WP next to Agrauxine, FR); (B2.39) Trichoderma atroviride, cepa n° V08 / 002387; (B2.40) Trichoderma atroviride, cepa n° NMI V08 / 002388; (B2.41) Trichoderma atroviride, cepa n° NMI V08 / 002389; (B2.42) Trichoderma atroviride, cepa n° NMI V08 / 002390; (B2.43) Trichoderma atroviride, cepa LC52 (p. ex., Tenet por Agrimm Technologies Limited); (B2.44) Trichoderma atroviride, cepa ATCC 20476 (IMI 206040); (B2.45) Trichoderma atroviride, cepa T11 (IMI352941 / . Petição 870250021756, de 19 / 03 / 2025, pág. 61 / 233 58 / 107 CECT20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g., Trichodex® from Makhteshim, US); (B2.49) Trichoderma harzianum, in particular strain KD (e.g., Trichoplus from Biological Control Products, SA (acquired by Becker Underwood)); (B2.50) Trichoderma harzianum, strain ITEM 908 (e.g., Trianum-P from Koppert); (B2.51) Trichoderma harzianum, strain TH35 (e.g., Root-Pro from Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g., SoilGard 12G from Certis, US); (B2.53) Trichoderma viride, cepa TV1 (eg, Trianum-P por Koppert); (B2.54) Ampelomyces quisqualis, em particular from strain AQ 10 (eg, AQ 10® by IntrachemBio Italia); (B2.56) Aureobasidium pullulans, em particular blastospores from onion DSM14940; (B2.57) Aureobasidium pullulans, em particular blastospores from onion DSM 14941; (B2.58) Aureobasidium pullulans, in particular mixtures of blastospores of strains DSM14940 and DSM 14941 (e.g., Botector® by bio-ferm, CH); (B2.64) Cladosporium cladosporioides, strain H39 (por Stichting Dienst Agricultural Research); (B2.69) Gliocladium catenulatum (Synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g., Prestop ® by AgBio Inc. and also, e.g., 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 P-16511); (B2.77) Trichoderma atroviride , strain SKT-3 (FERM P-17021); (B2.78) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, e.g., 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 BINAB Bio-Innovation AB, Sweden); (B2. 81) Trichoderma stromaticum (e.g., Tricovab per. Petition 870250021756, dated 03 / 19 / 2025, p. 62 / 233 59 / 107 Ceplac, Brazil); (B2. 83) Ulocladium oudemansii, in particular strain HRU3 (e.g. Botry-Zen® by Botry-Zen Ltd, NZ); (B2. 84) Verticillium albo-atrum (formerly V. dahliae), strain WCS850 (CBS 276.92; e.g., Dutch Trig by Tree Care Innovations); (B2. 86) Verticillium chlamydosporium; (B2. 87) mixtures of Trichoderma asperellum strain ICC 012 and Trichoderma gamsii strain ICC 080 (product known as e.g. BIO-TAMtm from Bayer CropScience LP, US).

[0208] Additional examples of biological control agents that may be combined with the compounds of formula (I) and compositions comprising them are:

[0209] bacteria selected from the group consisting of Bacillus cereus, in particular B. cereus, strain CNCM I-1562 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, B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (nematode Rotylenchulus reniformis)-PR3 (ATCC Accession Number SD-5834), Streptomyces microflavus cepa AQ6121 (= QRD 31.013, NRRL B-50550), and Streptomyces galbus cepa AQ 6047 (NRRL Accession No. 30232);

[0210] 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 strain IFPC 200613, or strain Apopka 97 (ATCC Accession No. 20874), and Paecilomyces lilacinus, in particular P lilacinus strain 251 (AGAL 89 / 030550); Petition 870250021756, dated 03 / 19 / 2025, p. 63 / 233 60 / 107

[0211] selected viruses from the group consisting of Adoxophyes orana (summer fruit tortricids) granulovirus (GV), Cydia pomonella (apple moth) granulovirus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beetroot caterpillar) mNPV, Spodoptera frugiperda (fall armyworm) mNPV and Spodoptera littoralis (cotton worm) NPV.

[0212] bacteria and fungi that can be added as 'inoculants' to plants or plant parts or plant organs and that, due to their specific 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.

[0213] 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, Armour-Zen, 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 powder or mustard powder.

[0214] Examples of insecticides, acaricides and nematicides, respectively, Petition 870250021756, dated 19 / 03 / 2025, p. 64 / 233 61 / 107 that could be mixed with the compounds of formula (I) and compositions comprising them are:

[0215] (1) Acetylcholine esterase (AChE) inhibitors, such as 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, fanfur, 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, propetanphos, protiophos, pyraclophos, pyridafenthion, quinalfos, sulfotep, tebupirimphos, temefos, terbufos, tetrachlorvinphos, thiometon, triazofos, trichlorfon and vamidothion.

[0216] (2) GABA-dependent chloride channel blockers, such as, for example, cyclodiene organochlorides, for example, chlordane and endosulfan or phenylpyrazoles (fiprols), for example, etiprol and fipronil.

[0217] (3) Sodium channel modulators, such as, for example, pyrethroids, e.g., acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, s-cyclopentenyl bioallethrin isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyfenothrin [(1R)-trans-isomer], deltamethrin, empentrin [(EZ)-(1R)-isomer], esfenvalerate, Petition 870250021756, dated 03 / 19 / 2025, page 65 / 233 62 / 107 etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadetrin, monofluorothrin, permethrin, phenothrin [(1R)-transisomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer)], tralomethrin and transfluthrin or DDT or methoxychlor.

[0218] (4) Competitive modulators of nicotinic acetylcholine receptor (nAChR), such as, for example, neonicotinoids, e.g., acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupiradifurone.

[0219] (5) Allosteric modulators of nicotinic acetylcholine receptor (nAChR), such as, for example, spinosyns, e.g. e.g., spinetoram and spinosad.

[0220] (6) Allosteric modulators of glutamate-dependent chloride channels (GluCl), such as, for example, avermectins / milbemycins, for example, abamectin, emamectin benzoate, lepimectin and milbemectin.

[0221] (7) Mimics of juvenile hormone, such as, for example, juvenile hormone analogues, e.g., hydroprene, quinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0222] (8) Various non-specific inhibitors (multisite), such as, for example, alkyl halides, e.g., methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartrate emetic generators or methyl isocyanate, e.g., diazomet and metam.

[0223] (9) Chordonal Organ Modulators, such as pimetrozine or flonicamide.

[0224] (10) Mite growth inhibitors, such as clofentezine, hexthiazine and diflovidazine or ethoxazole.

[0225] (11) Microbial disruptors of the insect intestinal membrane, such as, for example, Bacillus thuringiensis subspecies israelensis, Bacillus Petition 870250021756, dated 03 / 19 / 2025, page 66 / 233 63 / 107 sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis kurstaki subspecies, Bacillus thuringiensis tenebrionis subspecies, and Bt plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1.

[0226] (12) Mitochondrial ATP synthase inhibitors, such as ATP disruptors, for example, diafenthiuron or organotin compounds, for example, azocyclotine, cyexatine and fenbutatine oxide or propargite or tetradifon.

[0227] (13) Uncouplers of oxidative phosphorylation via disruption of the proton gradient, such as, for example, chlorfenapyr, DNOC and sulfluramide.

[0228] (14) Nicotinic acetylcholine receptor channel blockers, such as bensultap, cartap hydrochloride, thiocilam and thiosultap-sodium.

[0229] (15) Type 0 chitin biosynthesis inhibitors, such as bistrifluron, chlorfluazuron, diflubenzuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0230] (16) Chitin biosynthesis inhibitors, type 1, for example, buprofezin.

[0231] (17) Molt disruptor (in particular for Diptera, i.e., dipterans), such as cyromazine.

[0232] (18) Ecdysone receptor agonists, such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0233] (19) Octopamine receptor agonists, such as amitraz.

[0234] (20) Inhibitors of mitochondrial complex III electron transport, such as, for example, hydramethylnon or acequinoline or fluacripyrim.

[0235] (21) Inhibitors of mitochondrial complex I electron transport, such as, for example, from the METI acaricide group, e.g., phenazaquine, fenpyroximate, pirimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone Petition 870250021756, dated 03 / 19 / 2025, page 67 / 233 64 / 107 (Derris).

[0236] (22) Voltage-dependent sodium channel blockers, such as indoxacarb or metaflumizone.

[0237] (23) Acetyl CoA carboxylase inhibitors, such as, for example, tetronic and tetramic acid derivatives, e.g., spirodiclofen, spiromesifene and spirotetramat.

[0238] (24) Inhibitors of mitochondrial complex IV electron transport, such as, for example, phosphines, e.g., aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, e.g., calcium cyanide, potassium cyanide and sodium cyanide.

[0239] (25) Inhibitors of mitochondrial complex II electron transport, such as, for example, beta-ketonitrile derivatives, e.g., cyanopyrafene and cyflumethophene and carboxanilides, such as, for example, pirilubumide.

[0240] (28) Ryanodine receptor modulators, such as, for example, diamides, e.g., chlorantraniliprole, cyantraniliprole and flubendiamide,

[0241] additional active compounds such as, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclotiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Quinomethionate, Chlorprolethrin, Cryolite, Cyclaniliprol, Cycloxapride, Cyalodimide, Dichlormezothiaz, Dicofol, Epsilon-Metofluthrin, Epsilon-Monfluthrin, Flomethoquine, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopiram, Fluralaner, Fluxamethamide, Fufenozide, Guadipir, Heptafluthrin, Imidaclotiz, Iprodione, Kappa-Bifentrin, Kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Piridalil, Pirifluquinazone, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprol, Tetrachlorantraniliprol, Tigolaner, Thioxazafen, Thiofluoximate, Triflumezopyrim and iodomethane;In addition, preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), and also the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H Emission 870250021756, dated 03 / 19 / 2025, page 68 / 233; 65 / 107 1,2,4-triazol-5-amine (known from document no. WO2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1 -yl]-5-fluorospiro[indol-3,4'piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from document no. WO2003 / 106457) (CAS 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from document no. WO2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from document No. WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from document no. EP2647626) (CAS 1440516-42-6), 4-(but-2-in-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from document no. WO2004 / 099160) (CAS 792914-58-0), PF1364 (known from document no. 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 no. WO2012 / 029672) (CAS 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridilidene]-1,1,1-trifluoro-propan-2-one (known from document no. WO2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-carboxamide (known from document no. WO2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazol-3-carboxamide (known from document no. CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(c / s-1-oxide-3-thiethanyl)-benzamide, 4-[5-(3,5-dichlorophenyl) -4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1oxide-3-thiethanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-di-hydro-5-(trifluoromethyl)3-isoxazolyl]-2-methyl-N-(c / s-1-oxido-3-tiethanil)benzamide (acquired from document no. WO 2013 / 050317 A1) (CAS 1332628),- N-[3-chloro-1-(3-pyridinyl)1 H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide, (+)-N-[3-chloro-1 Petition 8702500 / 10.17253, de 69 / 233, 66 / 107 (3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide and (-)-N[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from documents No. WO 2013 / 162715 A2, WO 2013 / 162716 A2, 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 document no. CN 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 document no. CN 103109816 A) (CAS 1232543-85-9);N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazol-5-carboxamide (known from document no. 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 no. WO 2011 / 085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (known from document no. CN 101337940 A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hyhydrazinecarboxamide (known from document no. CN 101715774 A) (CAS 1232543-85-9); ester of 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2yl)phenyl-cyclopropanecarboxylic acid (known from document no. 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 document no. CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-, 1-[N-[4-[1-[4(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-manopyranose (known from document no. US 2014 / 0275503 A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl)-Petition 870250021756, dated 03 / 19 / 2025, p. 70 / 233; 67 / 107 pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-ant / )-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-azabicyclo[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 (known from documents no. WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide (known from documents no. WO 2015 / 058021 A1, WO 2015 / 058028 A1) (CAS 1477919-27-9) and N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)1H-pyrazol-5-carboxamide (known from document no. CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from document No. WO 2013 / 115391 A1) (CAS 1449021-97-9), 3(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one (known from documents No. WO 2010 / 066780 A1, WO 2011 / 151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8diazaspiro[4.5]decane-2,4-dione (known from document no. WO 2014 / 187846 A1) (CAS 1638765-58-8), methyl ester of 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4,5]dec-3-en-4-yl-carbonic acid (known from documents no. WO 2010 / 066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinilidene]-2,2,2-trifluoroacetamide (known from documents no. DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)pyridinilidene]-2,2,2-trifluoroacetamide, (known from document no. WO 2016005276 A1) (CAS 1689566-03-7), [N(Z)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)pyridinilidene]-2,2,2-trifluoroacetamide, (CAS 1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from documents no. WO 2011 / 105506 A1, WO 2016 / 133011 A1). Petition 870250021756, dated 03 / 19 / 2025, page 71 / 233 68 / 107 (CAS 1332838-17-1).

[0242] 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, dichlormide, fenclorazol (-ethyl), fenclorim, flurazol, fluxofenim, furilazol, isoxadifeno (-ethyl), mefenpir (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)-amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0243] Examples of herbicides that could be mixed with the compounds of formula (I) and compositions comprising them are:

[0244] Acetochlor, acifluorfeno, acifluorfeno sodium, aclonifeno, alachlor, alidoclor, aloxidim, aloxidim sodium, ametrina, amicarbazona, amidoclor, amidosulfurona, acido 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5fluoropyridine-2-carboxylic acid, aminociclopyraclor, aminociclo-pirachlor de potassium, aminociclopirachlor de methyl, aminopiralida, amitrol, sulfamato de ammonium, anilofos, asulam, atrazine, azaphenidine, azimsulfuron, beflubutamida, benazolin, benazolin de etila, benfluralin, benfuresate, bensulfuron, bensulfuron de methyl, bensulide, bentazona, benzobiciclon, benzofenap, biciclopiron, bifenox, bilanafos, bilanafos sódico, bispiribac, bispiribac sódico, bromacil, bromobutida, bromofenoxim, bromoxinil, butirato de bromoxinil, potassium, heptanoato, e octanoato, busoxinona, butaclor, butafenacil, butamifos, butenaclor, butralin, butroxidim, butilato, cafenstrol, carbetamida, carfentrazona, carfentrazona de etila, cloramben, clorbromuron, clorfenac, clorfenac sódico, clorfenprop,chlorflurenol, methyl chlorflurenol, cloridazon, chlorimuron, ethylachlorophthalim chlorimuron, chlorotoluron, dimethyl chlortal, chlorsulfuron, cinidon, ethyl cynidon, cimethylin, cinosulfuron, clacifos, clethodim, clodinafop, propargyl clodinafop, clomazone, clomeprop, clopyralid, cloransulam, methyl cloransulam, cumiluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, Petition 870250021756, dated 03 / 19 / 2025, page 72 / 233 69 / 107 ciclosulfamuron, cicloxidim, cialofop, cialofop de butila, ciprazina, 2,4-D, 2,4-D-butotil, -butila, -dimetilamônio, -diolamin, -etila, -2-etilexila, isobutila, -isooctila, -iso-propilaamônio, -potássio, -triisopropanolamônio e -trolamina, 2,4-DB, 2,4-DB de butila, dimetilamônio, -isooctila, -potássio e -sódio, daimuron (dymron), dalapon, dazomet, n-decanol, desmedifam, pirazolato de detosila (DTP), dicamba, diclobenil, 2-(2,4dichlorobenzil)-4,4-dimethyl-1,2-oxazolidin-3-ona, 2-(2,5-dichlorobenzil)-4,4-dimethyl-1,2oxazolidin-3-ona, dichlor-prop, dichlorprop-P, diclofop, diclofop de methyla, diclofop-P de methyla, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr sodium, dimefuron, dimepiperate, dimethaclor, dimetamethrin, dimethenamida, dimetenamidaP, dimetrasulfuron, dinitramine, dinoterb, difenamida, diquat, diquat-dibromid, dithiopir, diuron, DNOC, endothal, EPTC, esprocarb, etalfluralin, etametsulfuron, etametsulfuron de methyla, ethiozin, ethofumesate, etoxifen,ethyl ethoxyfen, ethoxysulfuron, ethobenzanide, F-9600, F-5231, i.e. N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5oxo-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethanesulfonamide, F-7967, i.e. 3-[7-chloro5-fluoro-2-(trifluoro-methyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, ethyl fenoxaprop, ethyl fenoxa-prop-P, fenoxasulfone, phenquinotrione, fentrazamide, flamprop, flamprop-M isopropyl, methyl flamprop-M, flaza-sulfuron, florasulam, fluazifop, fluazifop-P, butyl fluazifop, butyl fluazifop-P, flucarbazone, sodium flucarbazone, flucetosulfuron, fluchloralin, flufenacet, ethyl flufenpyr, flumetsulam, flumiclorac, pentyl flumiclorac, flumioxazin, fluometuron, flurenol, butyl flurenol, methyl dimethylammonium, fluoroglycophene, ethyl fluoroglycophene, flupropanate, flupyrsulfurone, sodium flupyrsulfuronmethyl, fluridone, flurochloridone, fluroxypyr, fluroxypyrmeptyl, flurtamone,flutiacet, methyl flutiacet, fomesafene, sodium fomesafene, foransulfurone, fosamine, glyphosinate, ammonium glyphosinate, sodium glyphosinate-P, ammonium glyphosinate-P, sodium glyphosate-P, glyphosate, ammonium glyphosate, isopropyl ammonium, diammonium, dimethylammonium, -potassium, -sodium and trimesium, H, Petition 870250021756, dated 03 / 19 / 2025, page 73 / 233 70 / 107 9201, that is, O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halauxifene, methyl halauxifene, halosaphene, halosulfuron, methyl halosulfuron, haloxifop, haloxifop-P, haloxifop-ethoxyethyl, haloxifop-P-ethoxyethyl, methyl haloxifop, methyl haloxifop-P, hexazinone, HW-02, that is, 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate, imazametabenz, methyl imazametabenz, imazamox, ammonium imazamox, imazapic, ammonium imazapic, imazapyr, imazapyr-isopropylammonium, imazaquine, ammonium imazaquine, imazethapyr, imazethapyr of imium, imazosulfurone, indanofan, indaziflam, iodosulfuron, iodo-sulfuron-methyl-sodium, ioxynil, ioxynil octanoate, potassium and sodium, ipfencarbazone, iso-proturon, isouron, isoxaben, isoxaflutol, carbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotil, -dimethylammonium,-2-ethylhexyl, isopropylammonium, potassium and sodium, MCPB, methyl MCPB, ethyl and sodium, mecoprop, mecoprop sodium and butotil, mecoprop-P, mecoprop-P-butotil, dimethylammonium, 2-ethylhexyl and potassium, mefenacet, mefluidide, mesosulfuron, methyl mesosulfuron, mesotrione, metabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, metabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, methoxuron, metribuzin, metsulfuron, methyl metsulfuron, molinat, monolinuron, monosulfuron, monosulfuron ester, MT-5950, i.e., N-(3-chloro-4-isopropylphenyl)-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)-methanone, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargila, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat,paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlor-phenol, pentoxazone, petoxamide, petroleum oils, phenmedifam, picloram, picolinafen, pinoxaden, piperofos, pretilachlor, primisulfuron, Petition 870250021756, dated 03 / 19 / 2025, page 74 / 233 71 / 107 primisulfuron de methyl, prodiamine, profoxidim, prometon, prometrina, propachlor, propanil, propaquizafop, propazine, profam, propisoclor, propóxi-carbazona, propoxicarbazona de sódio, propirisulfuron, propizamida, prosulfocarb, prosulfuron, piraclonil, piraflufen, piraflufen de ethyl, pirasulfotol, pyrazolinato (pyrazolato), pirazosulfuron, pirazosulfuron de ethyl, pirazoxifen, piribambenz, piribambenz de isopropila, piribambenz de propila, piribenzoxim, piributycarb, piridafol, piridato, piriftalida, piriminobac, piriminobac de methyl, pirimisulfan, piritiobac, piritiobac de sodium, pyroxasulfona, piroxsulam, quinclorac, quinmerac, quino-clamine, quizalofop, quizalofop de etila, quizalofop-P, quizalofop-P de etila, quizalofop-P-tefurila, rimsulfuron, saflufenacil, setoxidim, siduron, simazine, simethrin, SL-261, sulcotrion, sulfentrazona, sulfometuron, sulfometuron de methyla, sulfosulfuron, SYN-523, SYP 249, ou seja, 1-etoxi-3-metil-1-oxobut-3-en-2-il 5-[2-cloro-4-(trifluorometil)fenoxi]-2nitrobenzoato, SYP-300, ou seja, 1-[7-fluoro-3-oxo-4-(prop-2-in-1-il)-3,4-di-hidro-2H1,4-benzoxazin-6-il]-3-propil-2-tioxoimidazolidina-4,5-diona, 2,3,6-TBA, TCA (ácido tricloroacetico), TCA de sódio, tebutiuron, tefuriltriona, tembotriona, tepraloxidim, terbacil, terbucarb, terbumeton, terbutilazin, terbutrin, tenilclor, thiazopir, tiencarbazona, tiencarbazona de methyl, tifensulfuron, tifensulfuron de methyl, thiobencarb, tiafenacil, tolpiralate, topramezona, tralcoxidim, triafamona, tri-alato, triasulfuron, triaziflam, tribenuron, tribenuron de methyl, triclopyr, triethazine, trifloxysulfuron, trifloxysulfuron sodium, trifludimoxazin, trifluralin, triflusulfuron, methyl triflusulfuron, trito-sulfuron, urea sulfate, vernolate, what follows composed of: Petition 870250021756, dated 03 / 19 / 2025, p. 75 / 233 72 / 107

[0245] Examples of plant growth regulators are:

[0246]

[0246] Acibenzolar, methyl acibenzolar-S, 5-aminolevulinic acid, ancimidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, chlorprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, sodium dikegulac, endotal, dipotassium endotal, disodium endotal, e-mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, butyl flurenol, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, chloride mepiquat, 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, prohexadione, calcium prohexadione, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, ethyl trinexapac, tsitodef, uniconazole,uniconazole-P., Methods and uses

[0247] The compounds of formula (I) and the compositions comprising them have potent microbicidal activity. They can be used to control unwanted microorganisms, such as unwanted fungi and bacteria. They can be particularly useful in protecting agricultural crops (they control microorganisms that cause plant diseases) or in protecting materials (e.g., industrial materials, forestry materials, stored goods) as described in more detail below in this document. More specifically, the compounds of formula (I) and the compositions comprising Petition 870250021756, dated 03 / 19 / 2025, page 76 / 233 73 / 107 These can be used to protect seeds, germinating seeds, emerged seedlings, plants, plant parts, fruits, harvested products and / or the soil in which the plants grow against unwanted microorganisms.

[0248] Control or controlling, as used in this document, encompasses the protective, curative, and eradicative treatment of unwanted microorganisms. Unwanted 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.

[0249] More specifically, the compounds of formula (I) and the compositions comprising them can be used as fungicides. For the purposes of this descriptive report, the term fungicide refers to a compound or composition that can be used in agricultural crop protection for the control of unwanted fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and / or for the control of Oomycetes, more preferably for the control of Basidiomycetes (causative agents of rust diseases).

[0250] The present invention also relates to a method for controlling unwanted 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 habitat (to plants, plant parts, seeds, fruits or the soil in which the plants grow).

[0251] Typically, when the compound and composition of the invention are used in curative or protective methods to control phytopathogenic fungi Petition 870250021756, dated 03 / 19 / 2025, page 77 / 233 74 / 107 and / or phytopathogenic oomycetes, an effective and plant-compatible quantity thereof is applied to the plants, plant parts, fruits, seeds, or to the soil or substrates in which the plants grow. Suitable substrates that can be used for plant cultivation 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. An effective and plant-compatible quantity means a quantity that is sufficient to control or destroy the fungi present or likely to appear in the growing area and that does not cause any appreciable symptoms of phytotoxicity to said agricultural crops.This quantity can 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 ability of one skilled in the art. Plants and plant parts

[0252] The compounds of formula (I) and compositions comprising them may be applied to any plants or parts of plants.

[0253] Plants means all plants and plant populations, such as wild plants or cultivated plants, whether desired or undesired (including naturally occurring agricultural crops). Agricultural crops may be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations thereof, including genetically modified plants (GMOs or transgenic plants) and plant cultivars that are eligible for and not eligible for protection under plant breeders' rights.

[0254] Plant parts are understood to be all parts and organs of plants. Petition 870250021756, dated 03 / 19 / 2025, page 78 / 233 75 / 107 above and below ground, such as shoots, leaves, flowers, and roots, examples of which include leaves, needles, stalks, stems, flowers, fruiting bodies, fruits, and seeds, as well as roots, tubers, and rhizomes. Plant parts also include harvested material and material from vegetative and generative propagation, for example, cuttings, tubers, rhizomes, seedlings, and seeds.

[0255] Plants that can be treated according to the methods of the invention include the following: cotton, flax, vine, fruits, vegetables, such as Rosaceae sp. (for example, 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. (for example, banana and plantain crops), Rubiaceae sp. (for example, coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example, lemons, oranges and grapefruit); Solanaceae sp. (for example, 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., maize, peat, 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, radish 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, chard, beet); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.

[0256] In some preferred modalities, species of wild plants and Petition 870250021756, dated 03 / 19 / 2025, p. 79 / 233 76 / 107 plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or fusion of protoplasts, and also parts thereof, are treated in accordance with the methods of the invention.

[0257] 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 parts thereof 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.

[0258] The methods according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g., plants or seeds. Genetically modified plants (or transgenic plants) are plants whose 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 nuclear, chloroplast, or mitochondrial genome, provides the transformed plant with new or improved agronomic properties or otherwise by expressing a protein or polypeptide of interest, or by downregulating or silencing another gene (or genes) that is 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 specific location in the plant genome is called a transformation event or transgenic event.

[0259] Plants and plant cultivars that can be treated by the methods Petition 870250021756, dated 03 / 19 / 2025, page 80 / 233 77 / 107 revealed above include all plants that have genetic material that confers useful and particularly advantageous characteristics to those plants (whether obtained through reproduction and / or biotechnological means).

[0260] 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, that is, said plants show improved defense against animal and microbial pests, such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.

[0261] 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 temperature, 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.

[0262] 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, increased germination efficiency and accelerated maturation. Yield may, in addition, 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, Petition 870250021756, dated 03 / 19 / 2025, page 81 / 233 78 / 107 number of seeds per pod or ear, seed weight, improved seed filling, reduced seed dispersal, reduced pod dehiscence, and lodging resistance. Additional yield characteristics include seed composition such as carbohydrate content and composition, e.g., cottonseed or starch, protein content, oil content and composition, nutritional value, reduction of antinutritional compounds, improved processability, and better storage stability.

[0263] 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 that generally results in higher yield, vigor, health and resistance to biotic and abiotic stresses.

[0264] 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, i.e., plants that have become tolerant to one or more given herbicides. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such herbicide tolerance.

[0265] 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, i.e., plants that have become resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such insect resistance.

[0266] Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated by the methods Petition 870250021756, dated 03 / 19 / 2025, page 82 / 233 79 / 107 revealed above include plants and plant cultivars that are tolerant to abiotic stresses. Such plants can be obtained through genetic transformation or by selecting plants containing a mutation that confers such stress resistance.

[0267] 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 altered quantity, quality and / or storage stability of the harvested product and / or altered properties of specific ingredients of the harvested product.

[0268] 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. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such altered fiber characteristics.

[0269] 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 oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such altered oil profile characteristics.

[0270] 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 oilseed plants or related Brassica, with altered shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation that confers such altered shattering characteristics and Petition 870250021756, dated 03 / 19 / 2025, page 83 / 233 80 / 107 includes plants such as oleaginous rapeseed plants with delayed or reduced grain shedding.

[0271] 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

[0272] The methods disclosed above can be used to control microorganisms, in particular phytopathogenic microorganisms such as phytopathogenic fungi, which cause diseases such as:

[0273] 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), Uncinula species (e.g., Uncinula necator);

[0274] diseases caused by rust disease pathogens, such as Gymnosporangium species (e.g., Gymnosporangium sabinae), Hemileia species (e.g., Hemileia vastatrix), Phakopsora species (e.g., Phakopsora pachyrhizi or Phakopsora meibomiae), Puccinia species (e.g., Puccinia recondita, Puccinia graminis or Puccinia striiformis), Uromyces species (e.g., Uromyces appendiculatus);

[0275] diseases caused by pathogens of 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), Pythium species (e.g., Pythium ultimum); Petition 870250021756, dated 03 / 19 / 2025, page 84 / 233 81 / 107

[0276] 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), Diaporthe species (e.g., Diaporthe citri), Elsinoe species (e.g., Elsinoe fawcettii), Gloeosporium species (e.g., Gloeosporium laeticolor), Glomerella species (e.g., Glomerella cingulate), Guignardia species (e.g., Guignardia bidwelli), Leptosphaeria species (e.g., Leptosphaeria maculans), Magnaporthe species (e.g., Magnaporthe grisea), Microdochium species (e.g., Microdochium nivale), Mycosphaerella species (e.g., Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis), Phaeosphaeria species (e.g., Phaeosphaeria nodorum), Pyrenophora species (e.g., Pyrenophora teres or Pyrenophora tritici repentis), Ramularia species (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),.

[0277] diseases of the roots and stems 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);

[0278] ear and panicle diseases (including maize ears) Petition 870250021756, dated 03 / 19 / 2025, page 85 / 233 82 / 107 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 purpurea), Fusarium species, (e.g., Fusarium culmorum), Gibberella species (e.g., e.g., Gibberella zeae), Monographella species, (e.g., Monographella nivalis), Stagnospora species, (e.g., Stagnospora nodorum);

[0279] diseases caused by smut fungi, for example, Sphacelotheca species (e.g., Sphacelotheca reiliana), Tilletia species (e.g., Tilletia caries or Tilletia controversa), Urocystis species (e.g., Urocystis occulta), Ustilago species (e.g., Ustilago nuda);

[0280] 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 (e.g., Sclerotinia sclerotiorum), Verticillium species (e.g., Verticillium alboatrum);

[0281] diseases of rot and rot transmitted by seeds from the soil, and also diseases of seedlings, caused, for example, by the species Alternaria (e.g., Alternaria brassicicola), the species Aphanomyces (e.g., Aphanomyces euteiches), the species Ascochyta (e.g., Ascochyta lens), the species Aspergillus (e.g., Aspergillus flavus), the species Cladosporium (e.g., Cladosporium herbarum), the species Cochliobolus (e.g., Cochliobolus sativus (conidia form: Drechslera, Bipolaris Syn: Helminthosporium)), species Colletotrichum (e.g., Colletotrichum coccodes), species Fusarium (e.g., Fusarium culmorum), species Gibberella (e.g., Gibberella zeae), species Macrophomina (e.g., Macrophomina phaseolina), species Microdochium (e.g., Microdochium nivale), species Monograph (p. ex., Monographella nivalis), Penicillium species (e.g., Penicillium expansum), Phoma species (e.g., Phoma lingam), Phomopsis species (e.g., Phomopsis sojae), Petition 870250021756, dated 03 / 19 / 2025, page 86 / 233 83 / 107 Phytophthora species (e.g., Phytophthora cactorum), Pyrenophora species (e.g., Pyrenophora graminea), Pyricularia species (e.g., Pyricularia oryzae), Pythium species (e.g., Pythium ultimum), Rhizoctonia species (e.g., Rhizoctonia solani), Rhizopus species (e.g., 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);

[0282] cancers, galls and witches' brooms caused, for example, by Nectria species (e.g., Nectria galligena);

[0283] wilting caused, for example, by Monilinia species (e.g., Monilinia laxa);

[0284] deformations of leaves, flowers and fruits caused, for example, by Exobasidium species (e.g., Exobasidium vexans), Taphrina species (e.g., Taphrina deformans);

[0285] degenerative diseases in woody plants, caused, for example, by Esca species (e.g., Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea), Ganoderma species (e.g., Ganoderma boninense);

[0286] diseases of flowers and seeds caused, for example, by Botrytis species (e.g., Botrytis cinerea);

[0287] tuber diseases caused, for example, by Rhizoctonia species (e.g., Rhizoctonia solani), Helminthosporium species (e.g., Helminthosporium solani);

[0288] 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).

[0289] In particular, compounds of formula (I) and compositions that Petition 870250021756, dated 03 / 19 / 2025, page 87 / 233 84 / 107 include the same and are effective in controlling phytopathogenic fungi that cause rust diseases. Seed Treatment

[0290] The method of controlling unwanted microorganisms can be used to protect seeds from phytopathogenic microorganisms, such as fungi.

[0291] The term “seed (or seeds)” as used in this document includes dormant seed, prepared seed, pre-germinated seed and seed with emerged roots and leaves.

[0292] Thus, the present invention also relates to a method for protecting seeds and / or agricultural crops from unwanted 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 (or compounds) 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.

[0293] Seed treatment can be carried out before sowing, at the time of sowing or immediately after.

[0294] When seed treatment is carried out before sowing (e.g., 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 (or compounds) of formula (I) or a composition comprising the same (as such or after dilution), the seeds and the compound (or compounds) of formula (I) or the composition comprising the same are mixed until a homogeneous distribution on the seeds is obtained. If suitable, the seeds may then be dried.

[0295] The invention also relates to seeds treated with one or more Petition 870250021756, dated 03 / 19 / 2025, p. 88 / 233 85 / 107 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 emerging from said treated seeds. A large part 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 small damage can result in the death of the plant.

[0296] Therefore, the present invention also relates to a method for protecting seeds, germinating plants and emerged seedlings, more generally to a method for protecting agricultural crops from phytopathogenic microorganisms, comprising the step of using seeds treated with one or more compounds of formula (I) or a composition comprising the same.

[0297] Preferably, the seed is treated in a state where it is sufficiently stable so that no damage occurs during 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, coverings, 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 immediately after preparation, or seeds stored in prepared or pre-germinated conditions, or seeds sown in nursery trays, ribbons or paper.

[0298] The amount of compound (or compounds) of formula (I) or Petition 870250021756, dated 03 / 19 / 2025, p. 89 / 233 86 / 107 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 especially 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 (or compounds) of formula (I) or composition comprising the same to be applied to the seed, in order to achieve optimal protection of the seed and the germinating plant with a minimum amount of compound (or compounds) of formula (I) or composition comprising the same being employed.

[0299] 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 metallic powders, granules, inactivated seed coating material, and also ULV formulations. The formulations may be ready-to-use formulations or may be concentrates that need to be diluted before use.

[0300] These formulations are prepared in a known manner, for example, by mixing the active ingredient or a mixture thereof with customary additives, for example, customary extenders and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins and also water.

[0301] These formulations are prepared in a known manner, by Petition 870250021756, dated 03 / 19 / 2025, page 90 / 233 87 / 107 mixture of active ingredients or combinations of active ingredients with customary additives, for example, customary extenders and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins and also water.

[0302] 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. Alkylnaphthalenesulfonates, such as diisopropyl- or diisobutylnaphthalenesulfonates, may be used preferably. 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.Non-ionic or anionic dispersants, or mixtures of non-ionic or anionic dispersants, may preferably be used. Useful non-ionic dispersants include especially ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristerilphenol polyglycol ethers, and phosphate or sulfate derivatives thereof. Suitable anionic dispersants are especially lignosulfonates, polyacrylic acid salts, and arylsulfonate / 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 preferably be used. Preservatives that may be present... Petition 870250021756, dated 03 / 19 / 2025, page 91 / 233 88 / 107 present in seed treatment formulations are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal. 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 customary binders usable in seed treatment products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tylose.

[0303] The compounds of formula (I) and the compositions comprising them are suitable for protecting seeds of any variety of plant 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. The treatment of wheat, soybean, rapeseed, maize and rice seeds is of particular importance.

[0304] 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

[0305] The compound of formula (I) can be applied as such or, by Petition 870250021756, dated 03 / 19 / 2025, page 92 / 233 89 / 107 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.

[0306] Application is carried out in the usual manner, for example, by watering, sprinkling, atomizing, diffusion, spraying, foaming, spreading and the like. It is also possible to apply the compound of formula (I) by the ultra-low volume method, via a drip irrigation system or irrigation application, to apply it in a furrow or inject it into the soil, stem or trunk. It is additionally possible to apply the compound of formula (I) by means of a wound seal, paint or other wound dressing.

[0307] 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 subject of the treatment (plant, plant part, fruit, seed or soil), the type of treatment (spraying, sprinkling, 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 agricultural crop and the environmental conditions.

[0308] 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 treatment of plant parts, such as leaves, the application rate can vary from 0.1 to 10000 g / ha, preferably from 10 to 1000 g / ha, more preferably from 50 to 300 g / ha (in the case of irrigation or drip application, it is still possible to reduce the application rate, especially when Petition 870250021756, dated 03 / 19 / 2025, p. 93 / 233 90 / 107 inert substrates such as rock wool or perlite are used). 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 10000 g / ha, preferably from 1 to 5000 g / ha.

[0309] These application rates are merely examples and are not intended to limit the scope of the present invention. Material Protection

[0310] 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 unwanted microorganisms.

[0311] In addition, the compound and composition of the invention can be used as antifouling compositions, individually or in combinations with other active ingredients.

[0312] 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 against microbial alteration or destruction may include adhesives, glues, paper, wallpaper and cardboard, textiles, carpets, leather, wood, fibers and fabrics, paints and plastic articles, cooling 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, Petition 870250021756, dated 03 / 19 / 2025, page 94 / 233 91 / 107 adhesives, sizes, paper and cardboard, leather, wood, inks, cooling lubricants and heat transfer fluids, with preference given to wood.

[0313] The compound and composition of the invention can prevent adverse effects such as rotting, decomposition, discoloration, color change or mold formation.

[0314] In the case of wood treatment, the compound and composition of the invention can also be used against fungal diseases likely to develop on or within the wood.

[0315] Wood means all types of wood species, and all types of wood 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.

[0316] The compound and composition of the invention can also be used to protect storage goods. Storage goods are understood to be natural substances of plant or animal origin or processed products thereof that are of natural origin and 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 unprocessed wood, such as timber for construction, poles and electricity barriers, or in the form of finished products, such as furniture. Storage goods of animal origin are, for example, animal hides, leather, skins and Petition 870250021756, dated 03 / 19 / 2025, page 95 / 233 92 / 107 hairs. The compound and composition of the invention can prevent adverse effects such as rotting, decomposition, discoloration, color alteration, or mold formation.

[0317] 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 preferably act against fungi, especially molds, wood-discoloring 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.

[0318] Aspects of the present teaching can be better understood in light of the following examples, which should not be interpreted as limiting the scope of the present teaching in any way. EXAMPLES

[0319] The following examples illustrate, but are not limited to, the preparation and effectiveness of the compounds of formula (I) according to the invention. Synthesis of compounds of formula I Petition 870250021756, dated 03 / 19 / 2025, p. 96 / 233 93 / 107 3-[4-(1-Benzofuran-3-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (compound I-002)

[0320] 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran (87 mg, 0.35 mmol) and [1,1-B / s(di-tert-butylphosphino)ferrocene]dichloropalladium (II) (11 mg, 0.016 mmol) were added to a solution of cesium carbonate (115 mg, 0.35 mmol) in water (0.8 ml) and a solution of 3-(4-bromophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (100 mg, 0.32 mmol) in dioxane (2.4 ml). The mixture was stirred at 85°C for 1 h and then cooled to rt. The reaction mixture was then concentrated and diluted with dichloromethane. The suspension was placed in a 2g 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 yield the title compound (54 mg, 48% yield).

[0321] MS (ESI): 348 [M+H]+ 3-[4-(Pyrazolo[1,5-a]pyrimidin-3-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2oxazol-5-ol (compound I-005)

[0322] A mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)pyrazolo[1,5-a]pyrimidine (54 mg, 0.39 mmol) and Tetraqu / s(triphenylphosphine)palladium (0) Petition 870250021756, dated 03 / 19 / 2025, page 97 / 233 94 / 107 (20 mg, 0.018 mmol) were added to 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 (100 mg, 0.32 mmol) in 1,2-dimethoxyethane (3 ml). The mixture was stirred at 80°C for 1 h and then cooled to rt. Water and dichloromethane were then added and the two layers were separated. The organic layer was filtered through 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 yield 3-(4'-fluoro[biphenyl]-4-yl)-5(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (57 mg, 50% yield).

[0323] 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine (87 mg, 0.36 mmol), 3-(4-bromophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (100 mg, 0.32 mmol), Tetraqu / s(triphenylphosphine)palladium (0) (19 mg, 0.016 mmol) and cesium carbonate (115 mg, 0.36 mmol) were dissolved in degassed dioxane (3 ml) and degassed water (1 ml). The mixture was stirred at 80°C for 1 h, cooled to rt and diluted in 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 yield the title compound (65 mg, 55% yield) as a yellow solid.

[0324] MS (ESI): 349 [M+H]+

[0325] The compounds in Table 1 were prepared in analogy to the examples given above. Table 1: Compounds according to formula (I) Petition 870250021756, dated 03 / 19 / 2025, pp. 98 / 233 95 / 107 (I) Ex No. 3.94[a] I.005 FH pyrazolo[1,5-a]pyrim idin-3-yl 2.46[a] I.006 FH pyrazolo[1,5-a]pyridin-3-yl 2.75[a] I.007 FH 1,3-benzothiazol-2-yl 3.62[a] I.008 FH 2-F 1 H-indole-6-yl 3.37[a] I.009 Cl H 1 H-indol-6-yl 3.34[a] 1.010 FH 3-F 1 H-indol-6-yl 3.34[a] 1.011 FH imidazo[1,2-a]pyrim idin-6-yl 1.23[a] I.012 FH - [1,3]thiazolo[4,5-c]pyridin-2-yl 2.00[a]

[0326] 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 using the following methods:

[0327] [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). Petition 870250021756, dated 03 / 19 / 2025, p. 99 / 233 96 / 107

[0328] [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).

[0329] [c]The logP value 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).

[0330] If more than one logP value is available within the same method, all values ​​are provided and separated by “+”.

[0331] Calibration was performed with linear chain alkanones (with 3 to 16 carbon atoms) with known logP values ​​(measurement of logP values ​​using retention times with linear interpolation between successive alkanones). Lambda-max values ​​were determined using UV spectra from 200 nm to 400 nm and peak values ​​from chromatographic signals. NMR peak lists

[0332] NMR data from selected examples are written in the form of 1H NMR peak lists. For each signal peak, the δ value in ppm and the signal intensity are listed in square brackets. Periods and commas are used as delimiters between the δ value - signal intensity pairs.

[0333] The list of peaks in an example therefore has the form:

[0334] δ1 (intensity1); δ2 (intensity2);..........; δι (intensityi);......; δn (intensityn)

[0335] 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 mid-signals and their relative intensity compared to the most intense signal in the spectrum can be shown. Petition 870250021756, dated 03 / 19 / 2025, pp. 100 / 233 97 / 107

[0336] To calibrate the chemical shift for 1H spectra, tetramethylsilane and / or the chemical shift of the solvent used were employed, especially in the case of spectra measured in DMSO. Therefore, in NMR peak lists, the tetramethylsilane peak may occur, but not necessarily.

[0337] 1H NMR peak lists are similar to classic 1H NMR printouts and therefore generally contain all the peaks that are listed in the classic NMR interpretation.

[0338] In addition, they may show signs of classical 1H NMR imprinting similar to solvents, stereoisomers of the target compounds, which are also the subject of the invention, and / or impurity peaks.

[0339] 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 the present 1H NMR peak lists and generally have on average a high intensity.

[0340] 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%).

[0341] Such stereoisomers and / or impurities may be typical for the specific preparation process. Therefore, their peaks may help to recognize the reproduction of the present preparation process by means of “fingerprint byproducts”.

[0342] An expert, 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 could be similar to the relevant peak in the classical 1H NMR interpretation. Petition 870250021756, dated 03 / 19 / 2025, pp. 101 / 233 98 / 107

[0343] Additional details on the description of NMR data with peak lists can be found in the publication “Citation of NMR Peaklist Data in Patent Applications” from Research Disclosure Database Number 564025. 1.001: 1H NMR (300.2 MHz, CDCI3): δ= 17.0718 (0.6); 15.3721 (0.6); 13.5108 (0.6); 9.5368 (16.0); 8.7410 (13.6); 8.7132 (15.0); 8.5800 (0.6); 8.1756 (6.2); 8.1476 (8.5); 8.0194 (10.2); 7.9952 (15.1); 7.9678 (5.6); 7.8681 (13.6); 7.8402 (13.8); 7.7885 (5.2); 7.7333 (9.2); 7.7081 (10.6); 7.6842 (5.0); 7.6446 (1.4); 7.6010 (0.9); 7.5892 (0.9); 7.5669 (0.8); 7.5222 (0.6); 7.4915 (0.6); 7.4322 (0.6); 7.4083 (0.6); 7.3567 (1.0); 7.3457 (1.3); 7.2985 (100.4); 7.2919 (25.7); 7.1844 (0.8); 7.1473 (0.7); 6.9476 (0.8); 4.4183 (0.6); 4.3693 (0.6); 4.1390 ​​(1.2); 4.1180 (1.2); 4.0844 (1.3); 4.0565 (1.3); 4.0181 (1.2); 3.9970 (1.2); 3.9539 (1.0); 3.9001 (1.1); 3.8628 (4.5); 3.8041 (7.4); 3.6646 (5.3); 3.6408 (3.1); 3.6060 (3.8); 3.5086 (0.7); 3.4236 (0.7); 3.2169 (0.6); 2.9932 (8.7); 2.9458 (0.7); 2.9153 (7.7); 2.6580 (0.6); 1.9363 (0.6); 1.9120 (0.6); 1.8646 (0.6); 1.8437 (0.7); 1.8156 (1.0); 1.7431 (1.6); 1.6147 (14.3); 1.4636 (1.4); 1.4532 (1.2); 1.4189 (1.2); 1.3647 (1.2); 1.3418 (1.1); 1.3248 (1.0); 1.2898 (1.3); 1.2441 (1.0);1.1996 (1.0); 1.1831 (1.0); 1.1658 (0.7); 1.1306 (0.6); 1.0580 (0.6); 0.2742 (0.6); 0.2334 (0.8); 0.1990 (0.6); 0.1867 (0.6); 0.1705 (0.8); 0.1609 (0.7); 0.1440 (0.6); 0.0373 (114.4); 0.0306 (28.2); -0.1512 (0.6); 1.002: RMN de1H (400.1 MHz, d6-DMSO): δ= 8.6559 (13.8); 8.5153 (15.2); 7.9954 (3.7); 7.9774 (4.3); 7.9742 (3.9); 7.9524 (1.2); 7.9016 (5.3); 7.8802 (16.0); 7.8587 (15.6); 7.8373 (5.2); 7.7058 (4.3); 7.6872 (4.7); 7.4498 (1.5); 7.4464 (1.8); 7.4316 (3.9); 7.4284 (3.7); 7.4124 (4.0); 7.4082 (6.2); 7.4048 (4.3); 7.3892 (4.1); 7.3863 (4.2); 7.3711 (1.6); 7.3682 (1.4); 4.0126 (4.5); 3.9663 (5.6); 3.6317 (3.5); 3.5853 (2.8); 3.3042 (127.2); 2.8904 (7.6); 2.7316 (6.5); 2.5050 (25.0); 2.5006 (33.1); 2.4962 (24.1); 1.2351 (0.4); 0.0079 (1.2); -0.0002 (22.8); -0.0084 (1.1) I.003: RMN de1H (400.2 MHz, d6-DMSO): δ= 8.7221 (0.9); 8.0685 (0.6); 8.0455 (0.7); 8.0235 (7.2); 8.0018 (2.2); 7.9975 (1.9); 7.9540 (2.6); 7.9280 (0.7); 7.9148 (4.2); 7.8936 (8.6); 7.8763 (1.6); 7.8704 (2.1); 7.8354 (6.5); 7.8143 (3.8); 7.4420 (0.7); 7.4386 (0.9); 7.4244 (2.5); 7.4206 (2.5); 7.4115 (2.8); 7.4069 (4.0); 7.4018 (2.4); 7.3930 (2.1); 7.3890 (2.0); 7.3750 (0.8); 7.3711 (0.6); 4.0024 (2.2); 3.9563 (2.8); 3.6235 (1.8); 3.5771 (1.5); 3.3297 (18.0); 2.8915 (16.0); 2.7499 (0.5); 2.7329 (14.2); 2.6766 (0.3); 2.6723 (0.4); 2.6175 (2.0); 2.5120 (34.4); 2.5078 (58.6); 2.5033 (70.5); 2.4988 (48.9); 2.4944 (23.0); 2.3346 (0.4); 2.3302 (0.4); 1.2378 (1.2); 0.0079 (0.5); -0.0002 (5.6) Petition 870250021756, dated 03 / 19 / 2025, pp. 102 / 233 99 / 107 1.004: 1H NMR (400.2 MHz, d6-DMSO): δ = 8.6941 (4.5); 8.0454 (4.4); 8.0241 (5.6); 7.9549 (2.2); 7.8675 (5.5); 7.8461 (4.4); 7.7091 (2.0); 7.6913 (2.2); 7.6690 (2.0); 7.6488 (2.3); 7.6473 (2.2); 7.6029 (5.1); 7.3874 (1.0); 7.3842 (1.1); 7.3692 (1.8); 7.3663 (2.0); 7.3490 (1.5); 7.3455 (1.4); 7.3130 (1.7); 7.3106 (1.8); 7.2938 (2.2); 7.2921 (2.2); 7.2757 (1.0); 7.2734 (1.0); 4.0145 (2.1); 3.9683 (2.6); 3.6301 (1.5); 3.5840 (1.2); 3.3314 (13.7); 2.8922 (16.0); 2.7340 (13.2); 2.7334 (13.3); 2.5134 (16.0); 2.5090 (28.4); 2.5044 (35.2); 2.4999 (24.3); 2.4953 (11.2); -0.0002 (3.2) 1,005: RMN de1H (300.2 MHz, d6-DMSO): δ= 9.2473 (1.4); 9.2415 (1.5); 9.2239 (1.5); 9.2181 (1.4); 8.9053 (4.6); 8.7571 (1.5); 8.7513 (1.5); 8.7435 (1.6); 8.7378 (1.4); 8.6509 (4.2); 8.3291 (2.9); 8.3005 (3.3); 7.8278 (3.2); 7.7992 (2.9); 7.2070 (1.4); 7,1934 (1,3); 7.1836 (1.3); 7.1700 (1.3); 4.0143 (1.2); 3.9528 (1.6); 3.6404 (1.0); 3.5796 (0.8); 3.3481 (16.0); 2.5339 (2.4); 2.5282 (5.2); 2.5221 (7.2); 2.5161 (5.3); 0.0187 (6.6) 1.006: NMR de1H (300.2 MHz, CDCI3): δ= 8.1816 (0.6); 7.7085 (0.6); 7.6621 (0.5); 7.2986 (1.9); 3.7524 (0.4); 2.0240 (0.4); 1.2781 (16.0); 0.0362 (1.6) 1.007: NMR de1H (300.2 MHz, CDCI3): δ = 8.2031 (1.8); 8.1751 (2.2); 8.1547 (1.1); 8.1280 (1.2); 8.0360 (2.7); 7.9828 (1.0); 7.9562 (1.1); 7.8278 (2.0); 7.7996 (1.8); 7.5952 (0.4); 7.5912 (0.5); 7.5673 (1.0); 7.5440 (0.6); 7.5400 (0.7); 7.4928 (0.6); 7.4890 (0.8); 7.4628 (0.9); 7.4422 (0.4); 7.4385 (0.5); 7.2996 (7.0); 3.8145 (0.6); 3.7555 (1.0); 3.6249 (0.7); 3.5659 (0.4); 2.9922 (16.0); 2.9107 (14.8); 1.6730 (1.3); 1.3953 (2.5); 0.0471 (0.4); 0.0362 (8.2) 1.008: RMN de1H (400.1 MHz, CDCI3): δ= 9.7881 (2.2); 8.0108 (3.4); 7.9723 (3.7); 7.9232 (1.5); 7.9029 (3.0); 7.8835 (1.8); 7.7040 (2.9); 7.6831 (3.4); 7.6664 (5.2); 7.5226 (2.8); 7.5020 (2.7); 7.4444 (2.6); 7.4121 (2.6); 7.3511 (12.6); 7.3437 (6.6); 7.2911 (4.0); 7.2851 (3.5); 6.5440 (3.7); 3.7921 (1.8); 3.7462 (2.9); 3.6091 (2.5); 3.5622 (1.5); 2.9604 (16.0); 2.8779 (15.5); 2.5770 (0.8); 2.4047 (15.4); 1.3346 (0.4); 1.2558 (5.9); 0.8781 (1.0); 0.8539 (1.0); -0.0002 (11.6); 0.0073 (6.4) 1.009: RMN de1H (400.1 MHz, d6-DMSO): δ= 11.1998 (1.5); 8.6346 (2.3); 7.9515 (1.7); 7.7935 (16.0); 7.7081 (3.4); 7.6479 (1.9); 7.6273 (2.2); 7.4108 (1.8); 7.4047 (1.9); 7.3810 (1.8); 7.3601 (1.5); 6.4632 (2.3); 3.9768 (0.9); 3.9302 (1.2); 3.6186 (1.8); 3.5719 (1.4); 3.2995 (30.1); 2.8921 (11.6); 2.7340 (9.5); 2.5096 (7.5); 2.5053 (14.3); 2.5009 (18.7); 2.4964 (13.3); 1.2413 (0.9); -0.0002 (9.9) I.010: NMR de1H (400.1 MHz, CDCl3): δ= 8.2901 (0.8); 8.0028 (2.3); 7.7343 (2.2); 7.7136 (2.4); 7.6372 (2.7); 7.6104 (1.2); 7.5908 (2.4); 7.5700 (1.5); 7.5172 (1.6); 7.5135 (1.8); 7.4892 (3.8); 7.4731 (1.6); 7.4690 (1.2); 7.3359 (1.9); 7.3153 (1.7); 7.2992 (1.8); 7.2921 (2.5); 7.2853 (1.8); 7.2581 (15.0); 6.6086 (1.5); 6.6034 (2.1); 4.1795 (0.4); 3.7541 (1.8); 3.7098 (2.7); 3.5573 (1.7); 3.5126 (1.1); 2.9533 (16.0); 2.8762 (14.4); 1.5735 (2.8); 1.2854 (0.7); 1.2570 (4.1); 0.8965 (0.4); 0.8806 (0.8); 0.8626 (0.6); 0.8533 (0.6); 0.8368 (0.5); -0.0002 (17.1) Petition 870250021756, dated 03 / 19 / 2025, pp. 103 / 233 100 / 107 1.011: 1H NMR (400.1 MHz, d6-DMSO): δ= 9.4470 (0.4); 9.4283 (3.8); 9.4221 (3.9); 9.0258 (2.0); 8.9640 (3.7); 8.9578 (3.5); 8.6616 (4.4); 8.6528 (1.9); 8.6211 (0.5); 8.2957 (2.6); 8.0027 (0.4); 7.9517 (3.0); 7.9351 (5.2); 7.9292 (3.8); 7.9076 (8.6); 7.8838 (8.4); 7.8625 (3.1); 7.8497 (1.0); 7.8285 (0.5); 7.7797 (5.4); 7.7549 (1.4); 7.6950 (0.5); 7.6752 (0.6); 7.3595 (0.5); 7.3383 (0.4); 6.8574 (0.3); 4.1825 (0.4); 4.1662 (0.4); 3.9991 (2.5); 3.9850 (0.5); 3.9675 (0.5); 3.9528 (3.3); 3.9392 (0.6); 3.9227 (0.4); 3.6365 (2.2); 3.5909 (1.8); 3.5598 (0.4); 3.5137 (0.3); 3.4094 (0.5); 3.3062 (340.3); 2.8947 (16.0); 2.7541 (0.6); 2.7364 (14.2); 2.5495 (0.5); 2.5074 (38.0); 2.5030 (50.3); 2.4987 (37.3); 1.4075 (3.2); 1.2371 (1.1); 1.1784 (0.4); 1.1592 (0.8); 1.1420 (0.4); 1.1256 (0.7); -0.0002 (11.7) I. 012: 1H NMR (400.2 MHz, d6-DMSO): δ= 9.3656 (6.1); 8.7889 (0.8); 8.5779 (3.4); 8.5644 (3.7); 8.2856 (3.1); 8.2712 (3.6); 8.2653 (6.4); 8.2441 (7.1); 7.9594 (7.0); 7.9385 (5.8); 7.8827 (0.4); 7.8621 (0.5); 7.6928 (0.5); 7.6721 (0.4); 6.5479 (0.4); 4.0593 (2.5); 4.0130 (3.2); 3.6574 (2.2); 3.6109 (1.8); 3.3451 (55.7); 2.8922 (16.0); 2.7493 (0.4); 2.7333 (13.9); 2.7323 (14.2); 2.6783 (0.4); 2.6737 (0.6); 2.6696 (0.4); 2.5135 (38.1); 2.5093 (72.4); 2.5048 (92.5); 2.5003 (67.2); 2.4960 (33.2); 2.3360 (0.4); 2.3315 (0.5); 2.3272 (0.4); 1.3097 (1.2); 0.0079 (0.4); 0.0002 (9.6); -0.0084 (0.4) BIOLOGICAL DATA Example: preventive in vivo test in Puccinia recondita (brown rust in wheat) Solvent 5% by volume Dimethyl Sulfoxide 10% by volume of Acetone Emulsifier 1 μl of Tween® 80 per mg of active ingredient

[0344] 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.

[0345] 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.

[0346] 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 870250021756, dated 03 / 19 / 2025, page 104 / 233 101 / 107

[0347] 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.

[0348] 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.006

[0349] 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.005; I.007; I.008

[0350] 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.001 Example: preventive in vivo test on Phakospora pachyrhizi (soybean rust) Solvent 5% by volume Dimethyl Sulfoxide 10% by volume of Acetone Emulsifier 1 μl of Tween® 80 per mg of active ingredient

[0351] 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.

[0352] 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.

[0353] After 24 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Phakospora pachyrhizi spores. The contaminated soybean plants were incubated for 24 hours at 24°C and 100% Petition 870250021756, dated 03 / 19 / 2025, page 105 / 233 102 / 107 relative humidity and then for 10 days at 24°C and 70-80% relative humidity.

[0354] 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.

[0355] 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.001; I.005 Example. In vitro cell test of Pyricularia oryzae DMSO solvent: Culture Medium: 14.6 g of anhydrous D-glucose (VWR), 7.1 g of Mycological Peptone (Oxoide), 1.4 g of granulated yeast extract (Merck), QSP 1 liter Inoculum: spore suspension

[0356] 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%.

[0357] A suspension of Poryzae spores was prepared and diluted to the desired spore density.

[0358] The fungicides were evaluated for their ability to inhibit spore germination and mycelial growth in a liquid culture assay. The compounds were added at the desired concentration to the culture medium containing spores. After 5 days of incubation, the fungal toxicity of the compounds was determined by spectrometric measurement of mycelial growth. Fungal growth inhibition was determined by comparing absorbance values ​​in wells containing the fungicides with the absorbance in control wells without fungicides. Petition 870250021756, dated 03 / 19 / 2025, pp. 106 / 233 103 / 107

[0359] 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

[0360] 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.001; I.002; I.005; I.006; I.008; I.009; I.010 Example. In vitro cell test of Rhizoctonia solani' DMSO solvent: Culture Medium: 14.6 g of anhydrous D-glucose (VWR), 7.1 g of Mycological Peptone (Oxoide), 1.4 g of granulated yeast extract (Merck), QSP 1 liter mycelial suspension inoculum

[0361] 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%.

[0362] The inoculum was prepared from a preculture of R. solani grown in liquid medium by homogenization using a mixer. The concentration of ground mycelium in the inoculum was estimated and adjusted to the desired optical density (OD).

[0363] Fungicides were evaluated for their ability to inhibit mycelial growth in a liquid culture assay. The compounds were added at the desired concentrations to the culture medium containing the mycelial suspension. After 5 days of incubation, the fungicidal efficacy of the compounds was determined by spectrometric measurement of mycelial growth. Fungal growth inhibition was determined by comparing the absorbance values ​​in wells containing the fungicides with the absorbance in control wells without fungicides. Petition 870250021756, dated 03 / 19 / 2025, page 107 / 233 104 / 107 fungicides.

[0364] 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.006

[0365] 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.002; I.008; I.009; I.010 Example. In vitro cell test of Colletotrichum lindemuthianum DMSO solvent: Culture Medium: 14.6 g of anhydrous D-glucose (VWR), 7.1 g of Mycological Peptone (Oxoide), 1.4 g of granulated yeast extract (Merck), QSP 1 liter Inoculum: spore suspension

[0366] 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%.

[0367] A spore suspension of C. lindemuthianum was prepared and diluted to the desired spore density.

[0368] The fungicides were evaluated for their ability to inhibit spore germination and mycelial growth in a liquid culture assay. The compounds were added at the desired concentration to the culture medium containing spores. After 6 days of incubation, the fungal toxicity of the compounds was determined by spectrometric measurement of mycelial growth. Fungal growth inhibition was determined by comparing absorbance values ​​in wells containing the fungicides with the absorbance in control wells without fungicides. Petition 870250021756, dated 03 / 19 / 2025, pp. 108 / 233 105 / 107

[0369] 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.009

[0370] 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.007

[0371] 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.001; I.002; I.005; I.006; I.008; I.012 Example: preventive in vivo 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

[0372] 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 in water to the desired concentration.

[0373] To test 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 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 a relative atmospheric humidity of 95%.

[0374] The plants remained in the incubation chamber at approximately 24°C and a relative atmospheric humidity of approximately 80% and a day / night interval of 12 h. Petition 870250021756, dated 03 / 19 / 2025, page 109 / 233 106 / 107

[0375] 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 was 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

[0376] 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 in water to the desired concentration.

[0377] 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 h without light in an incubation chamber at approximately 24°C and a relative atmospheric humidity of 95%.

[0378] The plants remained in the incubation chamber at approximately 24°C and a relative atmospheric humidity of approximately 80% and a day / night interval of 12 h.

[0379] Two days after inoculation, the plants were sprayed with the active compound preparation at the indicated application rate and remained in the incubation chamber.

[0380] 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 was observed. Example: in vivo lasting activity test in Phakopsora (soybean) test Solvent: 24.5 parts by weight of acetone Petition 870250021756, dated 03 / 19 / 2025, page 110 / 233 107 / 107 24.5 parts by weight of dimethyl sulfoxide Emulsifier: 1 part by weight of polyoxyethylene sorbitan monooleate

[0381] 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 in water to the desired concentration.

[0382] To test the long-lasting 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 atmospheric humidity of approximately 80% and a day / night interval of 12 h.

[0383] 8 days after application, the plants were inoculated with an aqueous suspension of spores of the causal agent of soybean rust (Phakopsora pachyrhizi) and remained for 24 h without light in the incubation chamber at approximately 24°C and a relative atmospheric humidity of 95 .

[0384] The plants remained in the incubation chamber at approximately 24°C and a relative atmospheric humidity of approximately 80% and a day / night interval of 12 h.

[0385] 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 was observed.

Claims

1. A compound characterized in that it is selected from the group consisting of: 3-(4-quinazolin-2-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-benzofuran-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-benzothiophen-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-benzofuran-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1-benzofuran-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-pyrazolo[1,5-a]pyrimidin-3-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-pyrazolo[1,5-a]pyridin-3-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[2-fluoro-4-(1H-indol-6-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[chloro(difluoro)methyl]-3-[4-(1H-indol-6-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[3-fluoro-4-(1H-indol-6-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-imidazo[1,2-a]pyrimidin-6-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol and 3-[4-([1,3]thiazolo[4,5-c]pyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,or a salt or N-oxide thereof.

2. Composition CHARACTERIZED in that it comprises at least one compound of formula (I), as defined in claim 1, and at least one agriculturally acceptable carrier.

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

4. 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 a composition, as defined in claim 2, to plants, plant parts, seeds, fruits or the soil in which the plants grow.