Hydroxyisoxazoline compounds and derivatives thereof, composition, use of said compound and method for the control of phytopathogenic fungi.
Novel hydroxy-isoxazoline compounds offer improved fungicidal properties, enhancing control of phytopathogenic fungi by addressing environmental and economic demands.
Patent Information
- Authority / Receiving Office
- BR · BR
- Patent Type
- Patents
- Current Assignee / Owner
- BAYER AG
- Filing Date
- 2020-06-18
- Publication Date
- 2026-07-07
AI Technical Summary
There is a need for new fungicidal compounds that address growing environmental and economic demands, including improvements in spectrum of action, safety profile, selectivity, application rate, residue formation, and prevention of fungicide resistance.
Development of novel hydroxy-isoxazoline compounds and their derivatives, which can be used as fungicides, offering improved performance in controlling phytopathogenic fungi.
The novel hydroxy-isoxazoline compounds provide enhanced efficacy in controlling phytopathogenic fungi, addressing the limitations of existing fungicides.
Abstract
Description
"HYDROXY-ISOXAZOLINE COMPOUNDS AND DERIVATIVES THEREOF, COMPOSITION, USE OF SAID COMPOUND AND METHOD FOR THE CONTROL OF PHYTOPATHOGENIC FUNGI" TECHNICAL FIELD
[001] The present invention relates to the use of hydroxy-isoxazolines and derivatives thereof as fungicides. It also relates to new derivatives of hydroxy-isoxazolines, to their use as fungicides and to compositions comprising them. FUNDAMENTALS
[002] 3-Phenyl isoxazolines and their use as herbicides or insecticides are known from WO 99 / 05130, WO 2019 / 034602 and WO 2009 / 051956. Isoxazole derivatives are known to be useful as crop protection agents to combat or prevent infestations by microorganisms. For example, WO 2015 / 129773 discloses isoxazole derivatives that can be used as fungicides. WO 2006 / 031631 discloses substituted isoxazoles that can be used for the control of microbial pests, particularly fungal pests, in plants. More recently, hydroxy-isoxazoles have been disclosed as useful for the control of phytopathogenic fungi (WO 2018 / 202487).
[003] Several fungicidal agents have been developed so far. However, the need remains for the development of new fungicidal compounds in order to meet the growing environmental and economic demands placed on modern crop protection agents and compositions. This includes, for example, improvements in spectrum of action, safety profile, selectivity, application rate, residue formation and favorable preparation capacity. It may also be desirable to have new compounds to prevent the emergence of fungicide resistance. Petition 870260051039, dated 05 / 28 / 2026, page 5 / 314 2 / 149
[004] The present invention provides novel fungicidal compounds that have advantages over known compounds and compositions in at least some of these respects. SUMMARY
[005] The present invention relates to compounds of formula (I): (I) where R1, R2, X, m, ne Het are recited in this report, as well as their salts, N-oxides and solvates.
[006] The present invention relates to a composition comprising at least one compound of formula (I), as defined in this report, and at least one agriculturally suitable carrier.
[007] The present invention relates to a method for controlling phytopathogenic fungi comprising the step of applying at least one compound of formula (I), as defined in this report, or a composition, as defined in this report, to plants, plant parts, seeds, fruits or the soil in which the plants grow. DEFINITIONS
[008] The term “alkyl”, as used in this report, in the context of alkyl or alkylsulfonyl, alkylsulfinyl, alkylthio, alkylamino, for example, should be understood as preferably meaning branched and unbranched alkyl, meaning, for example, methyl, ethyl, n-propyl, / so-propyl, n-butyl, / so-butyl, tert Petition 870260051039, dated 05 / 28 / 2026, p. 6 / 314 3 / 149 butyl, sec-butyl, pentyl, / so-pentyl, hexyl, heptyl, octyl, nonyl and decyl and isomers thereof.
[009] The term “haloalkyl”, as used in this report, should preferably be understood to mean branched and unbranched alkyl, as defined above, in which one or more of the hydrogen substituents are substituted in the same or different ways by halogen. Particularly and preferably, said haloalkyl is, for example, chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromobutyl, trifluoromethyl, iodoethyl and isomers thereof.
[010] The term “alkoxy”, as used in this report, should preferably be understood to mean branched and unbranched alkoxy, meaning, for example, methoxy, ethoxy, propyloxy, / so-propyloxy, butyloxy, / so-butyloxy, tert-butyloxy, sec-butyloxy, pentyloxy, / so-pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy and dodecyloxy and isomers thereof.
[011] The term “haloalkoxy”, as used in this report, should 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, for example, chloromethoxy, fluoromethoxy, pentafluoroethoxy, fluoropropyloxy, difluoromethyloxy, trichloromethoxy, 2,2,2-trifluoroethoxy, bromobutyloxy, trifluoromethoxy, iodoethoxy and isomers thereof.
[012] The term “carbocyclyl”, as used in this report, refers to a non-aromatic carbon-containing mono- or polycyclic (fused, spiro or bridged) ring that may be saturated or partially unsaturated, with 3 to 10 carbon atoms in the ring or 3 to 7 carbon atoms. Examples of carbocyclyl include cycloalkyl and cycloalkenyl groups. Examples of saturated carbocyclyl, also referred to in this report as “cycloalkyl”, include, but are not limited to Petition 870260051039, dated 05 / 28 / 2026, p. 7 / 314 4 / 149 cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl groups. Examples of partially unsaturated carbocyclyl groups include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl or cyclodecenyl groups, wherein the linkage of said cycloalkyl group to the remainder of the molecule may be provided by a single or double bond.
[013] The term “heterocyclyl”, as used in this report, refers to three- to ten-membered, preferably three- to nine-membered, saturated or partially unsaturated heterocycles (including mono-, bi- or tricyclic heterocycles) containing one to four heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. If the ring contains more than one oxygen atom, they are not directly adjacent. A polycyclic heterocyclyl may contain fused, spiro or bridging ring junctions. Examples of heterocyclyl group include, but are not limited to, oxiranyl, aziridinyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2thiazolidinyl,4-tiazolidinila, 5-tiazolidinila, 2-imidazolidinila, 4-imidazolidinila, 1,2,4oxadiazolidin-3-ila, 1,2,4-oxadiazolidin-5-ila, 1,2,4-tiadiazolidin-3-ila, 1,2,4tiadiazolidin-5-ila, 1,2,4-triazolidin-3-ila, 1,3,4-oxadiazolidin-2-ila, 1,3,4-tiadiazolidin-2ila, 1,3,4-triazolidin-2-ila, 2,3-di-hidrofur-2-ila, 2,3-di-hidrofur-3-ila, 2,4-di-hidrofur-2ila, 2,4-di-hidrofur-3-ila, 2,3-di-hidrotien-2-ila, 2,3-di-hidrotien-3-ila, 2,4-di-hidrotien-2ila, 2,4-di-hidrotien-3-ila, 2-pirrolin-2-ila, 2-pirrolin-3-ila, 3-pirrolin-2-ila, 3-pirrolin-3-ila, 2-isoxazolin-3-ila, 3-isoxazolin-3-ila, 4-isoxazolin-3-ila, 2-isoxazolin-4-ila, 3isoxazolin-4-ila, 4-isoxazolin-4-ila, 2-isoxazolin-5-ila, 3-isoxazolin-5-ila, 4-isoxazolin-5-ila, 2-isotiazolin-3-ila, 3-isotiazolin-3-ila, 4-isotiazolin-3-ila 2-isotiazolin-4-ila, 3Petição 870260051039, on 05 / 28 / 2026, page. 8 / 314, 5 / 149 isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin5-yl, 2,3-di-hydropyrazol-1-yl, 2,3-di-hydropyrazol-2-yl, 2,3-di-hydropyrazol-3-yl, 2,3-di hydropyrazol-4-yl, 2,3-di-hydropyrazol-5-yl, hydropyrazol-3-yl, 3,4-di-hydropyrazol-4-yl, hydropyrazol-1-yl, 4,5-di-hydropyrazol-3-yl, 3,4-di-hydropyrazol-1-yl, 3,4-di3,4-di-hydropyrazol-5-yl, 4,5-di4,5-di-hydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-di-hydrooxazol-2-yl, 2,3-di-hydrooxazol-3-yl, 2,3-di-hydrooxazol-4-yl, 2,3-di-hydrooxazol-5-yl, 3,4-di-hydrooxazol-2-yl, 3,4-di-hydrooxazol-3-yl, 3,4-di-hydrooxazol-4-yl, 3,4-di-hydrooxazol-5-yl, 3,4-di-hydrooxazol-2-yl, 3,4-di-hydrooxazol-3-yl, 3,4-di-hydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5yl, 2-tetra-hydropyranyl, 4-tetra-hydropyranyl, 2-tetra-hydrothienyl, 3-hexhydropyridazinyl, 4-hexhydropyridazinyl, 2-hexhydropyridinyl, 4hexhydropyridinyl, 5-hexhydropyridinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2yl, 1,2,4-hexahydrotriazin-3-yl, indole-1-yl, indole-2-yl, indole-3-yl, indole-4-yl, indole-5yl, indole-6-yl, indole-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazole-5-ila, indazol-1-ila, indazol-3-ila, indazol-4-ila, indazol-5-ila, indazol-6-ila, indazol-7-ila,indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 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-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl. This definition also applies to heterocyclyl as part of a composite substituent, for example, heterocyclylalkyl etc., unless defined elsewhere., Petition 870260051039, 05 / 28 / 2026, p. 9 / 314 6 / 1
[014] The term “halogen” or “Hal”, as used in this report, should be understood to mean fluorine, chlorine, bromine or iodine.
[015] The term “halo” in parentheses (for example, “C1-C6-(halo)alkyl”) designates the optional presence of one or more halogen substituents which may be the same or different.
[016] The term “alkenyl”, as used in this report, should preferably be understood to mean branched and unbranched alkenyl, for example, a vinyl group, propen-1-yl, propen-2-yl, but-1-en-1-yl, but-1-en-2-yl, but-2-en-1-yl, but-2-en-2-yl, but-1-en-3-yl, 2-methyl-prop-2-en-1-yl or 2-methyl-prop-1en-1-yl.
[017] The term “alkynyl”, as used in this report, should preferably be understood to mean branched and unbranched alkynyl, for example, an ethynyl group, prop-1-yn-1-yl, but-1-yn-1-yl, but-2-yn-1-yl or but-3-yn-1-yl.
[018] The term “aryl”, as used in this report, 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 should further be understood that when said aryl group is substituted by one or more substituents, said substituents may be in any position on said aryl rings. In particular, in the case of aryl being a phenyl group, said 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). Petition 870260051039, dated 05 / 28 / 2026, p. 10 / 314 7 / 149
[019] The term “heteroaryl”, as used in this report, refers to an aromatic ring system containing 5 to 15 member atoms, or 5 to 12 member atoms, of which carbons and one or more heteroatoms which may be identical or different selected from O, N, and S. If the ring contains more than one oxygen atom, they are not directly adjacent. The 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 8 to 15, or 8 to 12 member atoms (carbon and heteroatoms). The monocyclic heteroaryl may contain 5 to 8 member atoms. Examples of heteroaryl compounds include, but are not limited to, thiazolyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, thia4H-pyrazolyl, etc., and benzo derivatives thereof, such as, for example, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzotriazolyl, indazolyl, indolyl, isoindolyl, etc.; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, etc., and benzo derivatives thereof, such as, for example, quinolinyl, isoquinolinyl, etc.; or azocinyl, indolizinyl, purinyl, etc., and benzo derivatives thereof; or cinolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl or oxepinyl, etc. It should also be understood that, in the case where said heteroaryl group is replaced by one or more substituents, said substituents may occupy any one or more positions in said heteroaryl rings.Specifically, if heteroaryl is a pyridyl group, for example, said substituents may occupy any one or more of the positions 2, 3, 4, 5 and / or 6 with respect to the nitrogen atom in the pyridine ring. This definition also applies to heteroaryl as part of a compound substituent (e.g., heteroaryloxy). Petition 870260051039, dated 05 / 28 / 2026, p. 11 / 314 8 / 149
[020] As used in this report, the term “C1-C6”, for example, in the context of the definition of “C1-C6-alkyl” or “C1-C6-alkoxy”, should be understood as meaning a group with a finite number of carbon atoms from 1 to 6, that is, 1, 2, 3, 4, 5 or 6 carbon atoms.
[021] The terms “acyclic radicals”, as used in this report, in the expressions “in which acyclic radicals may be substituted” designate any of the acyclic groups recited in the paragraph preceding said expressions, or any acyclic portion of a composite group (for example, the C1-C8-alkyl portion of aryl-C1-C8-alkyl).
[022] The term “cyclic radicals”, as used in this report, in the expressions “in which cyclic radicals can be substituted” means any of the cyclic groups, whether alicyclic or aromatic, mentioned in the paragraph before said expressions, or any cyclic portion of a composite group (for example, the aryl portion of aryl-C1-C6-alkyl).
[023] In a group containing an acyclic moiety and a cyclic moiety (for example, aryl-C1-C6-alkyl), each of these moieties can be substituted independently of the other.
[024] The term “leaving group”, as used in this report, should be understood to mean a group that is displaced from a compound in a substitution or elimination reaction, for example, a halogen atom, a trifluoromethanesulfonate (“triflate”) group, alkoxy, methanesulfonate, ptoluenesulfonate, etc. DETAILED DESCRIPTION ACTIVE INGREDIENTS
[025] The present invention relates to compounds of formula (I): Petition 870260051039, dated 05 / 28 / 2026, page 12 / 314 9 / 149 (I) in which R1 is selected from the group consisting of hydrogen, Ci-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, -C1-C8-alkyl-aryl, -C1-Ce-alkylC1-Ce-alkoxy, -Si(C1-Ce-alkyl)3, -SiAryl(C1-C8-alkyl)2, -C1-C8-alkyl-C3-C8-cycloalkyl, aryl, heteroaryl, -C1-C8-alkyl-heteroaryl, di-C1-C8-alkylphosphate, -C(=O)Ra, C(=O)N(Ra)2, -C1-C6-alkyl-OC(=O)Rae -C1-C6-alkyl-C(=O)Ra, com Raselected from the group consisting of hydrogen, amino, C1-C10-alkyl, C1-C6-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylsulfanyl, C1-C8-alkylamino, di-C1-C8alkylamino, -C1-C6-alkyl-C1-C6-alkoxy, C3-Cw-carbocyclyl, C3-C10-halocarbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, heterocyclyloxy, aryloxy and heteroaryloxy,where the acyclic radicals R1 or Ra can be replaced by one or more substituents R1a and where the cyclic radicals R1 or Ra can be replaced by one or more substituents R1c; X is an atom of hydrogen, fluorine, or chlorine; M is 0, 1, or 2; Het is a heteroarila of 6 members; right? 0, 1, 2, 3 or 4; R2 is a substituent independently selected from the group consisting of halogen, cyano, hydroxyl, sulfanyl, sulfinyl, sulfonyl, amino, nitro, C1-C6. Petition 870260051039, dated 05 / 28 / 2026, page 13 / 314 10 / 149 alkyl, Ci-C6-haloalkyl, Ci-C6-hydroxyalkyl, Ci-C6-cyanoalkyl, Ci-C6-alkoxy, CiC6-haloalkoxy, Ci-C6-alkylamine, di-Ci-C6-alkylamino, C2-Calk6-C2-alkenyl C2-C6-hydroxyalkenyl, C2-C6-cyanoalkenyl, C2-C6-alkynyl, C2-Cehaloalkynyl, C2-C6-hydroxyalkynyl, C2-C6-cyanoalkynyl, Ci-C6-alkylsulfanyl, pentafluoro-Xe- Ci-C6-alkylsulfinyl, arylsulfinyl, Ci-Ce alkylsulfonyl, arylsulfonyl, C3-Cio-carbocyclyl, 3- to i0-membered heterocyclyl, aryl, heteroaryl, C3-Ci0-carbocyclyloxy, 3-to-heterocyclyloxy, aryloxy 10-membered -Si(Ci-Ce-alkyl)3, -C(=O)R21, -C(=O)OR21, -C(=O)N(R21)2,C(=O)N(OR2i)R2i, -C(=O)NR2iN(R2i)2,-C(=S)2,(R2i -C(=NR2i)R2i,C(=NR2i)N(R2i)2, -C(=NOR2i)R2i, -N(R2i)2, -NR2iC(=O)OR2i, -N(OR2i)C(=O)OR2i, NR2iC(=NR)O2)N(=R2i)N(R2i -N(OR2i)C(=S)R2i, -NR2iC(=S)R2i,NR2iC(=S)N(R2i)2, -NR2iC(=NR2i)R2i, -OC(=O)R2i, -OC(=O)N(R2i)2, NR21S2(=1 -N=CR21-N(R21)2, -S(=O)2R21, -S(=O)2N(R21)2,-P(=O)(OR21)2, -O-C1C6-(halo)alkyl-aryl, -Ci-C6-(halo)alkyl-C3-Ci0-carbocyclyl, -Ci-C6-(halo)alkyl-O-C3Ci0-carbocyclyl de -(3Cytero)Cyl6 members, -C1-C6 (halo)alkyl-O-heterocycler from 3 to i0 members, -Ci-C6-(halo)alkyl-aryl, -Ci-C6 (halo)alkyl-heteroaryl, -Ci-C6-(halo)alkyl-heteroaryl,-(Caryl2-Cal Ci-C6-(halo)alkyl-C(=O)R2i, -Ci-C6-(halo)alkyl-C(=O)OR2i, -Ci-C6-(halo)alkylC(=O)N(R2i)2, -Ci-C6-(halo)alkyl-C(iOR,=iO)N C(=O)NR2iN(R2i)2, -Ci-C6-(halo)alkyl-C(=S)N(R2i)2, -Ci-C6-(halo)alkyl-Ci-C6-(halo)alkylC(=NR21)R21, -Ci-Ce-(halo)alkyl-C(=NR21)N(R21)2, -Ci-C6-(halo)alkyl-C(=NOH)R21, Ci-C6-(halo)alkyl-N(R2i)2, -Ci-C6-(halo)alkyl-NR2iC(=O)OR2i, -Ci-C6-(halo)alkylN(OR21)C(=O)OR21, -C1-C6-(halo)N(C2=1-NR21) -C1-C6-(halo)alkylNR21C(=O)R21, -C1-C6-(halo)alkyl-N(OR21)C(=O)R21, -C1-C6-(halo)alkylNR21C(=S)R21, -C1-C6-(C2)(=1-SNR21) -C1-C6-(halo)alkylNR21C(=NR21)R21, -C1-C6-(halo)alkyl-OC(=O)R21, -C1-C6-(halo)alkyl-OC(=O)N(R21)2, -Ci-Ce-(halo)alkyl-NR21S(=O)2R21, -Ci-C6-(halo)alkyl-N=CR21-N(R21)2, -Ci-CePetition 870260051039, dated 28 / 05 / pá2026 14 / 314 11 / 149 (halo)alkyl-SR21, -Ci-C6-(halo)alkyl-S(=O)R21, -Ci-C6-(halo)alkyl-S(=O)OR21, -CiC6-(halo)alkyl-S(=O)2R21, -C1-C6-(halo)alkyl-S(=O)2OR21, -C1-Ce-(halo)alkylS(=O)2N(R21)2 and -C1-C6-(halo)alkyl-P(=O)(OR21)2, wherein R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, C3C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl and -C1-C6(halo)alkyl-aryl, in which the radicals R2 and R21acyclic radicals can be replaced by one or more R22a substituents; R2 and R21cyclic radicals can be replaced by one or more R22c substituents. R1a, R22a, R1ce R22csão independently selected from the group consisting of halogen atom, nitro, hydroxyla, cyano, carboxyla, amino, sulfanila, pentafluoro-X6-sulfanila, formila, carbamoila, carbamate, C1-C6-alkyla, C3C7-cicloalkyla, C1-C6-haloalkyla, C3-C8-halocicloalkyla, C2-C6-(halo)alkenila, C2C6-(halo)alkynila, C1-C6-alkylamino, di-C1-C6-alkylamino, -Si(C1-C6-alkyl)3, C1-C6(halo)alkoxyC1-C6-(halo)alkylsulfanila, C1-C6-(halo)alkylcarbonila, C1-C6alkylcarbamoila, 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; As long as the compost gives formula (I) it is not: 3-[4-(2-methoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(pyridin-3-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydroxy-1,2,2 3-[4-(pyrimidine-5-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(6-fluoropyridin-3-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydroxa,zol-1 N-(4-{4-[5-hydroxy-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-3-yl]phenyl}pyridine-2yl)acetamide, Petition 870260051039, dated 5 / 28 / 2026, p. 15 / 314 12 / 149 N-(5-{4-[5-hydroxy-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-3-yl]phenyl}pyridine-2yl)acetamide, 3-[4-(6-methoxypyridine-3-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(2-fluoropyridin-4-yl)phenyl]-5-(trifluoromethyl)-oxa,5-zol-2-5 3-[4-(pyridin-4-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(3-fluoropyridin-4-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydrol-zol-1,2 3-[4-(4-methoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol, 3-[4-(2-fluoropyridin-3-yl)phenyl]-5-(trifluoromethyl)-oxa,5-zol-2-5 3-[4-(3-methoxypyridine-4-yl)phenyl]-5-(trifluoromethyl)-4,5-di-hydro-1,2-oxazol-5-ol.
[026] The excluded compounds are disclosed in WO 2019 / 122393.
[027] The invention includes pure stereoisomers of the compound of formula (I) and any mixture of these isomers.
[028] Not covered in this report are compounds resulting from combinations that are contrary to natural laws and which the person skilled in the art would therefore exclude based on their specialist knowledge. For example, ring structures with three or more adjacent oxygen atoms are excluded.
[029] 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 both pure stereoisomers and any mixture of these isomers. Where a compound may be present in two or more tautomeric forms in equilibrium, reference to the compound by means of a tautomeric description shall be considered as including all tautomeric forms.
[030] 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 Petition 870260051039, dated 05 / 28 / 2026, p. 16 / 314 13 / 149 concerning 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 all possible mixtures, in all proportions.
[031] The compound of formula (I) may suitably be in its free form, salt form, N-oxide form or solvate form (e.g., hydrate).
[032] Depending on the nature of the substituents, the compound of formula (I) may be present in the form of the free compound and / or a salt thereof, such as an agriculturally active salt.
[033] Agriculturally active salts include acid addition salts of inorganic and organic acids, as well as salts of usual 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, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or di-unsaturated fatty acids with 6 to 20 carbon atoms, alkylsulfuric monoesters, alkylsulfonic acids (sulfonic acids with straight or branched chain alkyl radicals with 1 to 20 carbon atoms).Arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, carrying one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids with straight or branched alkyl radicals with 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, carrying one or two phosphonic acid radicals), where the alkyl and aryl radicals may carry other substituents, therefore, Petition 870260051039, dated 05 / 28 / 2026, page 17 / 314 14 / 149 example, p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
[034] Solvates of compounds of formula (I) or their salts are stoichiometric compositions of the compounds with solvents.
[035] Compounds of formula (I) can exist in multiple crystalline and / or amorphous forms. Crystalline forms include non-solvated crystalline forms, solvates, and hydrates.
[036] The compounds of formula (I) are referred to in this report as “active ingredients”.
[037] In some embodiments, in formula (I) above, R1 is selected from the group consisting of hydrogen, C1-C6-alkyl, C3-C8cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, -C1-C6-alkyl-aryl, -C1-Ce-alkyl-C1-Ce-alkoxy, -Si(C1-Ce-alkyl)3, -SiAryl(C1-Ce-alkyl)2, -C(=O)Ra, -C(=O)N(Ra)2, -C1-Ce-alkylOC(=O)Ra and -C1-C6-alkyl-C(=O)Ra, with Ras selected from the group consisting of C1-C10-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-alkoxy, C3-Cw-carbocyclyl, 3- to 10-membered heterocyclyl, aryl and heteroaryl. The acyclic or cyclic radicals R1 or Ra can be substituted as described in this report.
[038] In some embodiments, in formula (I) above, R1 is selected from the group consisting of hydrogen, C1-Cw-alkyl, -Si(C1-C6alkyl)3, -C(=O)Ra and -C1-C6-alkyl-C(=O)Ra, with Ras selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, -C1-C6-alkyl-C1-C6alkoxy, C3-C10-carbocyclyl, aryl and heteroaryl. The acyclic or cyclic radicals R1 or Ra may be substituted as described in this report.
[039] In some embodiments, in formula (I) above, R1 is selected from the group consisting of hydrogen, C1-C6-alkyl and -C(=O)Ra Petition 870260051039, dated 05 / 28 / 2026, p. 18 / 314 15 / 149 where Ra is a C1-C6 alkyl (e.g., methyl). The acyclic radicals R1 or Ra can be substituted as described in this report.
[040] In some embodiments, in formula (I) above, R1 is a hydrogen atom.
[041] In some embodiments, in formula (I) above, m represents 0 or 1.
[042] In some embodiments, in formula (I) above, m represents 1.
[043] In some embodiments, in formula (I) above, m represents 0.
[044] In some embodiments, in formula (I) above, Het is a 6-membered heteroaryl comprising one, two, or three nitrogen atoms.
[045] In some embodiments, in formula (I) above, Het is pyridinyl, pyridazinyl, pirimidinyl or pyrazinyl.
[046] In some embodiments, in formula (I) above, Het is pyridazinyl or pyrazinyl.
[047] In some embodiments, in formula (I) above, Het is pyridinyl or pirimidinyl.
[048] In some embodiments, in formula (I) above, X is a fluorine atom.
[049] In some embodiments, in formula (I) above, X is a hydrogen atom.
[050] In some embodiments, in formula (I) above, X is a chlorine atom.
[051] In some embodiments, in formula (I) above, R1 is a hydrogen atom and X is a fluorine atom or a chlorine atom. Petition 870260051039, dated 05 / 28 / 2026, page 19 / 314 16 / 149
[052] In some embodiments, in formula (I) above, n represents 0, 1 or 2.
[053] In some embodiments, in formula (I) above, n represents 0 or 1.
[054] In some other embodiments, in formula (I) above, n represents 2.
[055] In some embodiments, in formula (I) above,
[056] when R1 is hydrogen, X is fluorine, m is 0 and Het is 3-pyridinyl, 4-pyridinyl or 5-pyrimidinyl, n is not 0; and when R1 is hydrogen, X is fluorine, m is 0, Het is 3-pyridinyl or 4-pyridinyl and n is 1, R2 is not methoxy, fluorine or acetamide. In other words, in these embodiments, compounds are excluded, where R1 is hydrogen, X is fluorine, m is 0, Het is 3-pyridinyl, 4-pyridinyl or 5-pyrimidinyl and n is 0, and compounds are excluded, where R1 is hydrogen, X is fluorine, m is 0, Het is 3-pyridinyl or 4-pyridinyl, n is 1 and R2 is methoxy, fluorine or acetamide.
[057] In some embodiments, compounds are excluded, wherein, in formula (I) above, Het is pyridinyl or pyrimidinyl and n is 0, and compounds are excluded, wherein Het is pyridinyl, n is 1 and R2 is methoxy, fluorine or acetamide.
[058] In some embodiments, in formula (I) above, n is 1, 2, 3 or 4; and compounds are excluded, in which, in formula (I) above, n is 1 and R2 is methoxy, fluorine or acetamide.
[059] In some embodiments, in formula (I) above, 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, Petition 870260051039, dated 05 / 28 / 2026, page 20 / 314 17 / 149 arylsulfonyl, C3-Cio-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, C3-Cio-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, C(=O)R21, -ORC(21,=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, -NR21S(=O)2 -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-3 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, -C -C1-C6-(halo)alkyl-C(=O)R21, -C1C6-(halo)alkyl-C(=O)OR21, -C1-C6-(halo)alkyl-C(=O)N(R21)2, -C1-C6-(halo)alkylC(=O)N(OR)21,1 -C1-C6-(halo)alkyl-C(=O)NR21N(R21)2, -C1-C6-(halo)alkylC(=S)N(R21)2,-C1-C6-(halo)alquil-N(R21)2, -C1-C6-(halo)alquil-NR21C(=O)OR21, -C1C6-(halo)alquil-NR21C(=O)N(R21)2, -C1-C6-(halo)alquil-NR21C(=O)R21, -C1-C6(halo)alquil-NR21C(=S)R21, -C1-C6-(halo)alquil-NR21C(=S)N(R21)2, -C1-C6-(halo)alquilOC(=O)R21, -C1-C6-(halo)alquil-OC(=O)N(R21)2, -C1-C6-(halo)alquil-NR21S(=O)2R21, C1-C6-(halo)alquil-SR21, -C1-C6-(halo)alquil-S(=O)R21, -C1-C6-(halo)alquil-S(=O)OR21, -C1-C6-(halo)alquil-S(=O)2R21, -C1-C6-(halo)alquil-S(=O)2OR21e -C1-C6-(halo)alquilS(=O)2N(R21)2, where R21 is as described in this report, preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6(halo)alquila, aryla and -C1-C6-(halo)alquil-aryla. The roots R2 and R21acíclicos and the roots R2 and R21cíclicos can be replaced, as described in this report.,
[060] In some embodiments, in formula (I) above, 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., Petition 870260051039, dated 05 / 28 / 2026, page 21 / 314 18 / 149 example, dimethylamino), C1-C6-alkylsulfanyl (e.g., methylsulfanyl), C3-C10-carbocyclyl (preferably, C3-C6-carbocyclyl, e.g., cyclopropyl, cyclopentyl), aryl (e.g., phenyl), heteroaryl (preferably, 5- or 6-membered heteroaryl comprising one or two heteroatoms, e.g., thienyl, pyridinyl), -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-C1-Ce-(halo)alkyl-aryl, -C1-C6(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-aryl, -C1-C6(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21e -C1-C6-(halo)alkyl-C(=O)OR21 with R21 described in this report, preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl. The acyclic or cyclic radicals R2 and R21 may be substituted, as described in this report, preferably substituted by halogen or C1-C6-(halo)alkyl.
[061] Examples of suitable -C(=O)R21 radicals include -C(=O)-C1-C6(halo)alkyl (e.g., methyl carbonyl).
[062] Examples of suitable -C(=O)OR21 radicals include -C(=O)-O-C1-C6(halo)alkyl (e.g., tert-butyl oxycarbonyl).
[063] Examples of suitable -N(R21)2 radicals include -NH-C1-C6(halo)alkyl-aryl (preferably, -NH-C1-C6-(halo)alkyl-phenyl, for example, -NHCH2-phenyl).
[064] Examples of suitable -O-C1-C6-(halo)alkyl-aryl include -O-C1-C6(halo)alkyl-phenyl (e.g., -O-CH2-phenyl).
[065] Examples of suitable -C1-C6-(halo)alkyl-aryl include -C1-C6(halo)alkyl-phenyl (e.g., -CH2-phenyl).
[066] 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). Petition 870260051039, dated 05 / 28 / 2026, p. 22 / 314 19 / 149
[067] Examples of suitable -C1-C6-(halo)alkyl-OR21 include -C1-C6(halo)alkyl-O-C1-C6-(halo)alkyl (e.g., methoxyethyl).
[068] Examples of suitable -C1-C6-(halo)alkyl-C(=O)OR21 include C1-C6(halo)alkyl-C(=O)OH and C1-Ce-(halo)alkyl-C(=O)-OC1-Ce-(halo)alkyl.
[069] In some embodiments, in formula (I) above, R2 is independently selected from the group consisting of halogen, cyano, 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-alkynyl, C1-C6-alkylsulfanyl, aryl, heteroaryl, aryloxy, -C(=O)R21, -N(R21)2, -O-C1-C6(halo)alkyl-aryl and -C1-C6-(halo)alkyl-aryl with R21 described in this report, preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl, and wherein the acyclic and cyclic R2 radicals may be substituted, as described in this report, preferably substituted by halogen or C1-C6-(halo)alkyl.
[070] In some embodiments, in formula (I) above, n is 1, 2, 3 or 4, preferably n is 1 or 2, and R2 is independently selected from the group consisting of chlorine, bromine, iodine, cyano, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-cyanoalkyl, C2-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkynyl, C1-C6-alkylsulfanyl, aryl, heteroaryl, aryloxy, C(=O)R21, -N(R21)2, -O-C1-C6-(halo)alkyl-aryl and -C1-C6-(halo)alkyl-aryl, with R21 described in this report, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6(halo)alkyl-aryl, and wherein the acyclic and cyclic radicals R2 may be substituted, as described in this report, preferably substituted by halogen or C1-C6-(halo)alkyl. Petition 870260051039, dated 05 / 28 / 2026, page 23 / 314 20 / 149
[071] In some embodiments, in formula (I) above, R2 is independently selected from the group consisting of cyano, alkyl, C1-C6-haloalkyl, C2-C6-alkynyl and -C(=O)H,
[072] In some embodiments, in formula (I) above, R2 is independently selected from the group consisting of fluorine, chlorine, cyano, amino, methyl, ethyl, n-propyl, / so-propyl, n-butyl, / so-butyl, tert-butyl, sec-butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, hydroxymethyl, cyanomethyl, methoxy, ethoxy, propyloxy, / so-propyloxy, butyloxy, / so-butyloxy, tert-butyloxy, sec-butyloxy, difluoromethyloxy, trifluoromethyloxy, methylamino, dimethylamino, ethinyl, methylsulfanyl, phenyl, pyridinyl, phenyloxy, formyl, benzylamino, benzyloxy and benzyl, wherein phenyl, phenyloxy and pyridinyl may be substituted for fluorine.
[073] In some embodiments, in formula (I) above, n is 1, 2, 3 or 4, preferably n is 1 or 2, and R2 is independently selected from the group consisting of chlorine, cyano, amino, methyl, ethyl, n-propyl, / so-propyl, n-butyl, / so-butyl, tert-butyl, sec-butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, hydroxymethyl, cyanomethyl, ethoxy, propyloxy, / so-propyloxy, butyloxy, / so-butyloxy, tert-butyloxy, sec-butyloxy, difluoromethyloxy, trifluoromethyloxy, methylamino, dimethylamino, ethinyl, methylsulfanyl, phenyl, pyridinyl, phenyloxy, formyl, benzylamino, benzyloxy and benzyl, wherein phenyl, phenyloxy and pyridinyl may be substituted for fluorine.
[074] The definitions specified above of R1, R2, X, m, ne Het can be combined in various ways to provide sub-classes of the compounds, according to the invention.
[075] Non-limiting examples of subclasses of compounds include the subclasses described in this report below. Petition 870260051039, dated 05 / 28 / 2026, p. 24 / 314 21 / 149
[076] In some embodiments (referred to in this report as embodiment Ia), the compounds of the present invention are the compounds of formula (I) in what R1 is selected from the group consisting of hydrogen, C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, -C1-C8-alkyl-aryl, -C1-Ce-alkylC1-Ce-alkoxy, -Si(C1-Ce-alkyl)3, -SiAryl(C1-C8-alkyl)2, -C1-C8-alkyl-C3-C8-cycloalkyl, aryl, heteroaryl, -C1-C8-alkyl-heteroaryl, di-C1-C8-alkylphosphate, -C(=O)Ra, C(=O)N(Ra)2, -C1-C6-alkyl-OC(=O)Rae -C1-C6-alkyl-C(=O)Ra, com Raselected from the group consisting of hydrogen, amino, C1-C10-alkyl, C1-C6-haloalkyl, C2-C8-alkenyl, C2-C8-haloalkenyl, C2-C8-alkynyl, C2-C8-haloalkynyl, C1-C8-alkoxy, C1-C8-haloalkoxy, C1-C8-alkylsulfanyl, C1-C8-alkylamino, di-C1-C8-alkylamino, -C1-C6-alkyl-C1-C6-alkoxy, C3-C10-carbocyclyl, C3-C10-halocarbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, heterocyclyloxy, aryloxy and heteroaryloxywhere the acyclic radicals R1 or Ra can be replaced by one or more substituents R1a and where the acyclic radicals R1 or Ra can be replaced by one or more substituents R1c; m is 0 or 1; Het is a 6-membered heteroaryl group comprising one or two nitrogen atoms, preferably Het is pyridinyl, pyridazinyl, pyrimidinyl or pyrazinyl; Petition 870260051039, dated 05 / 28 / 2026, p. 25 / 314 22 / 149 X is an atom of hydrogen, fluorine, or chlorine; N is 0, 1 or 2, preferably 0 or 1; R2 is independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6hydroxyalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy, Cloch-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6haloalkynyl, C1-C6-alkylsulfanyl, arylsulfanyl, C1-C6-alkylsulfinil, arylsulfinil, C1C6-alkylsulfonyl, arylsulfonyl, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, C3-C10-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, -C(O21)(O21,=ORC) -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,C(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, -NR21S(=O)2R21, -NR21C(=R21) S(=O)2N(R21)2, -O-C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl,-C1C6-(halo)alkyl-O-C3-C10-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)alkylaryl, -C1-C6-(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, -C1C6-(halo)alkyl-C(=O)N(R21)2, -C1-C6-(halo)alkyl-C(=O)N(OR21)R21, -C1-C6(halo)alkyl-C(=O)NR21N(R21)2, -C1-C6-(halo)alkyl-C(=S)N(R21)2, -C1-C6-(halo)alkylN(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)OR21, -C1-C6-(halo)alkyl-NR21C(=O)N(R21)2, C1-C6-(halo)alkyl-NR21C(=O)R21, -C1-C6-(halo)alkyl-NR21C(=S)R21, -C1-C6(halo)alkyl-NR21C(=S)N(R21)2, -C1-C6-(halo)alkyl-OC(=O)R21, -C1-C6-(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, in which R21 is as described in this report,Preferably R21 is selected independently. Petition 870260051039, dated 05 / 28 / 2026, p. 26 / 314 23 / 149 from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6(halo)alkyl-aryl, wherein the acyclic radicals R2 and R21 may be substituted by one or more R22a substituents and the cyclic radicals R2 and R21 may be substituted by one or more R22c, R22a and R22c substituents described in this report.
[077] In some embodiments (referred to in this report as embodiment Ib), the compounds of the present invention are the compounds of formula (I) in what R1 is selected from the group consisting of hydrogen, C1-C6-alkyl, -Si(C1-C6-alkyl)3, -C(=O)Ra, and -C1-C6-alkylC(=O)Ra, with R1 selected from the group consisting of C1-C10-alkyl, C1C6-haloalkyl, C1-C6-alkoxy, -C1-C6-alkyl-C1-C6-alkoxy, C3-C10-carbocyclyl, aryl and heteroaryl, wherein the acyclic radicals R1 or Ra may be substituted by one or more substituents R1a and wherein the acyclic radicals R1 or Ra may be substituted by one or more substituents R1c; R1a and R1c disclosed in this report, m is 0 or 1; Het is a 6-membered heteroaryl group comprising one or two nitrogen atoms, preferably Het is pyridinyl, pyridazinyl, pyrimidinyl or pyrazinyl; X is an atom of hydrogen, fluorine, or chlorine; right, 0, 1 or 2, preferably 0 or 1; Petition 870260051039, dated 05 / 28 / 2026, p. 27 / 314 24 / 149 R2 is independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6hydroxyalkyl, C1-C6-cyanoalkyl, C1-C6-alkoxy, Cloch-C6-alkyl, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6haloalkynyl, C1-C6-alkylsulfanyl, arylsulfanyl, C1-C6-alkylsulfinil, arylsulfinil, C1C6-alkylsulfonyl, arylsulfonyl, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, aryl, heteroaryl, C3-C10-carbocyclyloxy, 3- to 10-membered heterocyclyloxy, aryloxy, heteroaryloxy, -CO -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,C(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, -NR21S(=O)2R21, -NR21C(=R21) S(=O)2N(R21)2, -O-C1-C6-(halo)alkyl-aryl, -C1-C6-(halo)alkyl-C3-C10-carbocyclyl,-C1C6-(halo)alkyl-O-C3-C10-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)alkylaryl, -C1-C6-(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, -C1C6-(halo)alkyl-C(=O)N(R21)2, -C1-C6-(halo)alkyl-C(=O)N(OR21)R21, -C1-C6(halo)alkyl-C(=O)NR21N(R21)2, -C1-C6-(halo)alkyl-C(=S)N(R21)2, -C1-C6-(halo)alkylN(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)OR21, -C1-C6-(halo)alkyl-NR21C(=O)N(R21)2, C1-C6-(halo)alkyl-NR21C(=O)R21, -C1-C6-(halo)alkyl-NR21C(=S)R21, -C1-C6(halo)alkyl-NR21C(=S)N(R21)2, -C1-C6-(halo)alkyl-OC(=O)R21, -C1-C6-(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, in which R21 is described in this report,Preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6(halo)alkyl-aryl, Petition 870260051039, dated 05 / 28 / 2026, p. 28 / 314 25 / 149 wherein the acyclic radicals R2 and R21 can be replaced by one or more substituents R22a and the cyclic radicals R2 and R21 can be replaced by one or more substituents R22c, R22a and R22c described in this report.
[078] In some embodiments (referred to in this report as embodiment Ic), the compounds of the present invention are the compounds of formula (I) in what R1 is selected from the group consisting of hydrogen, C1-C6-alkyl and -C(=O)Ra, wherein Ra is a C1-C6-alkyl (e.g., methyl), into which the acyclic radicals R1 or Ra may be substituted, as described in this report; m is 0 or 1; Het is a 6-membered heteroaryl group comprising one or two nitrogen atoms, preferably Het is pyridinyl, pyridazinyl, pyrimidinyl or pyrazinyl; X is an atom of hydrogen, fluorine, or chlorine, preferably fluorine or chlorine; N is 0, 1 or 2, preferably 0 or 1; R2 is independently selected from the group consisting of halogen, cyano, hydroxy, sulfanyl, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6hydroxyalkyl, 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-C6haloalkynyl, C1-C6-alkylsulfanyl, arylsulfanyl, C1-C6-alkylsulfinyl, arylsulfinyl, C1C6-alkylsulfonyl, arylsulfonyl, C3-C10-carbocyclyl, 3- to 10-membered heterocyclyl, Petition 870260051039, dated 05 / 28 / 2026, page 29 / 314 26 / 149 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(OR21,1,1 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(=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, -CO -C1-C6-(halo)alkyl-C3-C10-carbocyclyl, -C1C6-(halo)alkyl-O-C3-C10-carbocyclyl -C1-C6-(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-O-3 members, -C1-C6-(halo)alkyl, -C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-heteroaryloxy, -C1-C6(halo)alkyl-OR21, -C1-C6-(halo)alkyl-C(=,O) -C1-C6-(halo)alkyl-C(=O)OR21, -C1C6-(halo)alkyl-C(=O)N(R21)2, -C1-C6-(halo)alkyl-C(=O)N(OR21)R21, -C1-C6(halo)alkyl-C(=O)OR2 -C1-C6-(halo)alkyl-C(=S)N(R21)2, -C1-Ce-(halo)alkylN(R21)2, -C1-C6-(halo)alkyl-NR21C(=O)OR21,-C1-C6-(halo)alkyl-NR21C(=O)N(R21)2, C1-C6-(halo)alkyl-NR21C(=O)R21, -C1-C6-(halo)alkyl-NR21C(=S)R21, -C1-C6(halo)alkyl-NR21C(=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)2OR21 and -C1-C6-(halo)alkyl-S(=O)2N(R21)2, wherein R21 is described in this report, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6(halo)alkyl-aryl, wherein the acyclic radicals R2 and R21 may be substituted by one or more substituents R22 and the cyclic radicals R2 and R21 may be substituted by one or more substituents R22c, R22a and R22c described in this report.
[079] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), R1 is a hydrogen atom. Petition 870260051039, dated 05 / 28 / 2026, page 30 / 314 27 / 149
[080] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), Het is selected from the group consisting of pyridinyl, pyridazinyl, pyrimidinyl and pyrazinyl. In some of these embodiments, when Het is pyridinyl or pyrimidinyl, n is not 0; and when Het is pyridinyl and n is 1, R2 is not methoxy, fluorine or acetaminophen.
[081] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), X is hydrogen.
[082] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), X is fluorine.
[083] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), X is chlorine.
[084] In some embodiments, according to embodiment (Ia), (Ib) and (Ic), R1 is a hydrogen atom and X is a chlorine atom.
[085] In some embodiments, according to embodiment (Ia), (Ib) and (Ic), R1 is a hydrogen atom and X is a fluorine atom.
[086] In some embodiments, according to embodiment (Ia), (Ib) and (Ic), n is 1, 2, 3 or 4; and compounds are excluded, where n is 1 and R2 is methoxy, fluorine or acetamide.
[087] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), n is 1.
[088] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), n is 1 in is 0.
[089] 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, Petition 870260051039, dated 05 / 28 / 2026, page 31 / 314 28 / 149 isopropyl, butyl, isobutyl), C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-alkylamino (e.g. methylamino), di-C1-C6-alkylamino, C1-C6-alkylsulfanyl, C3-Cio-carbocyclyl, aryl (e.g. phenyl), heteroaryl, -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-C1-C6(halo)alkyl-aryl, -Ci-C6-(halo)alkylheterocyclyl 3 to 10 members, -C1-C6(halo)alkyl-aryl, -Ci-C6-(halo)alkylheteroaryl, -Ci-C6-(halo)alkyl-OR2ie -Ci-C6(halo)alkyl-C(=O)OR21com R21 being described in this report, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl. The acyclic and cyclic radicals R2 may be substituted, as described in this report, preferably substituted by halogen or C1-C6-(halo)alkyl.In some of these embodiments, R2 is independently selected from the group consisting of chlorine, bromine, iodine, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C1-C6-alkylsulfanyl, C3-C10-carbocyclyl, aryl (e.g., phenyl), heteroaryl, -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-C1-C6-(halo)alkylaryl, -C1-C6-(halo)alkyl-heterocyclyl of 3 to 10 members, -C1-C6-(halo)alkyl-aryl, C1-C6-(halo)alkyl-heteroaryl, -C1-C6-(halo)alkyl-OR21e -C1-C6-(halo)alkylC(=O)OR21 with R21 being described in this report, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl. The acyclic and cyclic radicals R2 may be substituted as described in this report; preferably substituted by halogen or C1-C6-(halo)alkyl.
[090] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), when Ri is hydrogen, X is fluorine, m is 0 and Het is 3-pyridinyl, 4-pyridinyl or 5-pyridinyl, n is not 0; and when Ri is hydrogen, X is fluorine, m is 0 and Het is 3-pyridinyl or 4-pyridinyl and n is 1, R2 is not methoxy, fluorine or acetamide. Petition 870260051039, dated 05 / 28 / 2026, page 32 / 314 29 / 149
[091] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), n is 1, 2, 3 or 4, preferably 1 or 2; and Het is pyridazinyl, pyrimidinyl or pyrazinyl.
[092] In some embodiments, according to embodiments (Ia), (Ib) and (Ic), n is 1, 2, 3 or 4, preferably 1 or 2; Het is pyridinyl, and R2 is independently selected from the group consisting of chlorine, bromine, iodine, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkoxy, C1-C6alkylamino, di-C1-C6-alkylamino, C1-C6-alkylsulfanyl, Ca-Cw-carbocyclyl, aryl (e.g., phenyl), heteroaryl, -C(=O)R21, -C(=O)OR21, -N(R21)2, -O-C1-C6-(halo)alkylaryl, -C1-C6-3 to 10 membered (halo)alkylheterocyclyl, -C1-C6-(halo)alkylaryl, C1-C6-(halo)alkylheteroaryl, -C1-C6-(halo)alkyl-OR21e -C1-C6-(halo)alkylC(=O)OR21 with R21 being described in this report, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl. The acyclic and cyclic radicals R2 may be substituted as described in this report; preferably substituted by halogen or C1-C6-(halo)alkyl.
[093] In some embodiments (referred to in this report as embodiment Id), the compounds of the present invention are the compounds of formula (I) Petition 870260051039, dated 05 / 28 / 2026, page 33 / 314 30 / 149 in which R1 is hydrogen; m is 0 or 1; Het is pyridinyl, pyridazinyl, pyrimidinyl or pyrazinyl; X is a fluorine or chlorine atom, preferably a fluorine atom; N is 0, 1, or 2; R2 is independently selected from the group consisting of halogen, cyano, 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-alkynyl, C1-C6-alkylsulfanyl, aryl, heteroaryl, aryloxy, -C(=O)R21, -N(R21)2, O-C1-C6-(halo)alkyl-aryl and -C1-C6-(halo)alkyl-aryl, with R21 being described in this report and wherein the acyclic and cyclic radicals R2 may be substituted as described in this report. Preferably, R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl and the acyclic and cyclic radicals R2 may be substituted by halogen or C1-C6-(halo)alkyl.
[094] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), n is 1 or 2, and R2 is independently selected from the group consisting of chlorine, bromine, iodine, cyano, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-cyanoalkyl, C2-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkynyl, C1-C6-alkylsulfanyl, aryl, heteroaryl, aryloxy, C(=O)R21, -N(R21)2, -O-C1-C6-(halo)alkyl-aryl and -C1-C6-(halo)alkyl-aryl, with R21 being described in this report, preferably R21 is independently selected from the group consisting of hydrogen, C1-C6-(halo)alkyl, aryl and -C1-C6-(halo)alkyl-aryl. The acyclic and cyclic R2 radicals can be substituted, Petition 870260051039, dated 05 / 28 / 2026, p. 34 / 314 31 / 149 as described in this report, preferably replaced by halogen or C16-(halo)alkyl.
[095] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), n is 1 or 2, and R2 is selected independently from the group consisting of cyano, alkyl, C1-C6-haloalkyl, C2-C6-alkynyl and -C(=O)H.
[096] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), n is 1 or 2, and R2 is independently selected from the group consisting of chlorine, cyano, amino, methyl, ethyl, n-propyl, / so-propyl, n-butyl, / so-butyl, tert-butyl, sec-butyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, hydroxymethyl, cyanomethyl, ethoxy, propyloxy, / so-propyloxy, butyloxy, / so-butyloxy, tert-butyloxy, sec-butyloxy, difluoromethyloxy, trifluoromethyloxy, methylamino, dimethylamino, ethinyl, methylsulfanyl, phenyl, pyridinyl, phenyloxy, formyl, benzylamino, benzyloxy and benzyl, wherein phenyl, phenyloxy and pyridinyl may be substituted for fluorine.
[097] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), n is 2.
[098] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), m represents 1.
[099] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), m represents 0.
[0100] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), Het is pyridazinyl or pyrazinyl. Petition 870260051039, dated 05 / 28 / 2026, p. 35 / 314 32 / 149
[0101] In some embodiments, according to embodiments (Ia), (Ib), (Ic) and (Id), Het is pyridinyl or pyrimidinyl. In some of these embodiments, Het is 2-pyridinyl.
[0102] The present invention also relates to any compounds of formula (I) disclosed in Table 1.
[0103] The present invention relates to compounds of formula (I) selected from the group consisting of 3-[4-[2-(methylamino)pyrimidin-5-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 6-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-2-carbonitrile, 3-[3-fluoro-4-(6-methoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[2-(4-fluorophenyl)pyridin-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-chloropyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[2-fluoro-4-(2-methoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-phenylpyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-pyridin-2-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[6-(trifluoromethyl)pyridin-2-yl]phenyl]-4H-1,2-oxazol-5-ol, 3-[4-[2-(dimethylamino)pyrimidin-5-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(6-chloropyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-methylpyrimidin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[chloro(difluoro)methyl]-3-[4-(6-methoxypyridin-3-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(3-chloropyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-phenylpyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[2-fluoro-4-(2-fluoropyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[chloro(difluoro)methyl]-3-[4-(2-fluoropyridin-4-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(3-methylpyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-methoxypyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(6-methylsulfanylpyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, Petition 870260051039, de 28 / 05 / 2026, pág. 36 / 314 33 / 149 3-[4-(2-methoxypyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-methylsulfanylpyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[3-fluoro-4-(6-fluoropyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-(4-(trifluoromethyl)pyrimidin-5-yl]phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(6-methylpyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-methylsulfanylpyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-propan-2-ylpyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-methoxypyrimidin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridino-2-carbonitrile, 3-[4-(2-methylpyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[5-(4-fluorophenyl)pyridin-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[2-(trifluoromethyl)pyrimidin-5-yl]phenyl]-4H-1,2-oxazol-5-ol,3-[4-[6-(benzylamino)pyridin-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[3-fluoro-4-(2-methoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[chloro(difluoro)methyl]-3-[4-(2-methoxypyridin-3-yl)phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(6-methoxypyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(6-methoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-chloropyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[2-fluoro-4-(6-methoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[3-fluoro-4-(2-fluoropyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[3-(4-fluorophenyl)pyridin-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-methylpyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[6-(4-fluorophenyl)pyridin-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-[4-[5-hidróxi-5-(trifluorometil)-4H-1,2-oxazol-3-yl]phenyl]pyrimidino-4carbonitrile, 5-[4-[5-hidróxi-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]2-oxazol-3-yl]phenyl]pyrimidine-2carbonitrile, Petition 870260051039, dated 05 / 28 / 2026, page 37 / 314 34 / 149 3-[4-(2-methylpyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(6-phenylpyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-phenylpyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2,6-difluoropyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-methylpyrazin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-aminopyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-fluoropyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-fluoropyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-fluoropyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(6-fluoropyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-(3-(trifluoromethyl)pyridin-4-yl]phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(2-ethynylpyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-ethynylpyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol,5-(trifluoromethyl)-3-[4-[6-(trifluoromethyl)pyridazin-3-yl]phenyl]-4H-1,2-oxazol-5-ol, 4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-2-carbonitrile, 3-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-2-carbonitrile, 3-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-4-carbonitrile, 2-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-4-carbonitrile, 3-[4-(3-methoxypyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[2-(hydroxymethyl)pyridin-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 2-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-3-carbonitrile, 3-[4-(2-fluoropyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 4-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-2-carbaldehyde, 3-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-2-carbaldehyde, 2-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridine-4-carbaldehyde,3-[4-(2-chloro-6-fluoropyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[6-(trifluoromethyl)pyridin-3-yl]phenyl]-4H-1,2-oxazol-5-ol, Petition 870260051039, de 28 / 05 / 2026, pág. 38 / 314 35 / 149 3-[4-(2,5-dichloropyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-aminopyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[2-(2-fluorophenóxi)pyridin-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[4-(trifluoromethyl)pyrimidin-2-yl]phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(2-hydroxypyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[2-[(2-methylpropan-2-yl)oxy]pyrimidin-5-yl]phenyl]-5-(trifluoromethyl)-4H-1,2oxazol-5-ol, 3-[4-(2-chloropyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(5-chloropyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(6-chloropyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-chloropyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-chloropyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-chloropyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-ethoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-ethoxypyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-fluoro-2-methoxypyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 2-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]-4(trifluoromethyl)pyridino-3-carbonitrile, 3-[4-[2-(difluoromethyl)pyridin-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-tert-butylpyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-propoxypyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[2-(difluoromethoxy)pyridin-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2,4-difluoropyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[2-(trifluoromethyl)pyridin-3-yl]phenyl]-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[4-(trifluoromethyl)pyridin-2-yl]phenyl]-4H-1,2-oxazol-5-ol, 3-[4-[5-(dimethoxymethyl)pyridin-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, Petition 870260051039, de 28 / 05 / 2026, pág. 39 / 314 36 / 149 3-[4-[2-[chloro(difluoro)methyl]pyridin-4-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[4-(2-fluoropyridin-4-yl)pyrimidin-2-yl]phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[6-methoxy-4-(trifluoromethyl)pyridin-3-yl]phenyl]-5-(trifluoromethyl)-4H-1,2oxazol-5-ol, 3-[4-(2-methoxypyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 5-(trifluoromethyl)-3-[4-[3-(trifluoromethyl)pyridin-2-yl]phenyl]-4H-1,2-oxazol-5-ol, 3-[4-(2-aminopyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-methylpyridin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(2-phenylmethoxypyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-fluoropyridin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(4-methylpyridazin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-[5-hydroxi-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyrazino-2-carbonitrile, 2-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyrimidino-4carbonitrile, 3-[4-(4-methoxypyrimidin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(3-methoxypyrazin-2-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 2-[2-[4-[5-hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridin-4yl]acetonitrile, 3-(4-pyrazin-2-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-(4-pyrimidin-2-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol, 3-[4-(6-methylpyridazin-3-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol and 3-[4-(2,5-difluoropyridin-4-yl)phenyl]-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol.
[0104] The compounds of formula (I), according to the present invention, can be used as fungicides (i.e., for the control of fungi). Petition 870260051039, dated 05 / 28 / 2026, page 40 / 314 37 / 149 phytopathogenic, in particular, fungi that cause rust diseases, or Oomycetes in crop protection). PROCESSES FOR THE PREPARATION OF FORMULA I COMPOUNDS
[0105] The compounds of formula (I) can be prepared according to the processes described in WO 2008 / 006561 and WO 2019 / 122393.
[0106] 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 Petition 870260051039, dated 05 / 28 / 2026, page 41 / 314 38 / 149 LC-MS liquid chromatography-mass spectrometry MS mass spectrometry NMR nuclear magnetic resonance spectroscopy: chemical substitutions (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-propanephosphonic acid TEA Triethylamine TFA trifluoroacetic acid THF Tetrahydrofuran
[0107] It should be understood that, when in aqueous medium, compounds of formula (I'), where R1 is hydrogen and R2, X, m, ne Het are defined in this report above, may be present in a reversible equilibrium with the corresponding open form (i.e., compounds of formula (I'-I)). X F Het The m R2)n HO I' I'-I General synthetic routes for compounds of general formula I
[0108] The present invention also relates to processes for the preparation of compounds of formula (I). Unless otherwise indicated, the radicals X, R1, R2, m, ne, Het have the meanings given above for the Petition 870260051039, dated 05 / 28 / 2026, p. 42 / 314 39 / 149 compounds of formula (I). These definitions apply not only to the final products of formula (I), but also to all intermediates.
[0109] The compounds of formula (I'), wherein R1 = H, can be prepared, according to process P1, by reacting diketones of formula (II) with hydroxylamine (or its hydrochloride salt) in the presence of a base, such as sodium hydroxide or sodium acetate in water, and / or in a solvent, such as ethanol (as previously described in J. Org. Chem., 1995, 60, 3907 to 3909) or in the presence of an acid, such as acetic acid, optionally in a solvent such as ethanol (as described, for example, in the Journal of Heterocyclic Chemistry, 2010, 47(6), 1310 to 1316). (I') (II) Process P1
[0110] Diketones of formula (II) can be prepared according to known procedures (see, for example, WO 2008006561), 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. Petition 870260051039, dated 05 / 28 / 2026, p. 43 / 314 40 / 149 (III) R2)n O(F)m m OO R2)n(φ P2 Process
[0111] It should be understood that the intermediates of formula (II), according to the invention, in which X, R2, m, ne Het are defined in this report above, may be present as the diketone form (as represented in the 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.
[0112] The compounds of formula (III) may be commercially available or may be prepared from readily available compounds according to known procedures.
[0113] The compounds of formula (I) can be prepared, according to process P3, by reacting the 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, the Journal of Heterocyclic Chemistry, 2005, 42(7), 1253 to 1255). Process P3 LG1—R1 (IV) (I) Petition 870260051039, dated 05 / 28 / 2026, p. 44 / 314 41 / 149
[0114] The compounds of formula (IV) may be commercially available or may be prepared from readily available compounds according to known procedures.
[0115] 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 means of a crosslinking 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, cesium carbonate) and a catalyst (such as, for example, Tetracis(triphenylphosphine)palladium (0)) in a solvent, such as, for example, dioxane and water. R1—O W1 ( F)m(V) (0 Process P4
[0116] The compounds of formula (V) can be prepared from readily available compounds in a manner analogous to processes P1 and P2.
[0117] 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 crosslinking reaction. Petition 870260051039, dated 05 / 28 / 2026, page 45 / 314 42 / 149
[0118] 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 means of a crosslinking 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, Tetracis(triphenylphosphine)palladium (0)), in a solvent, such as, for example, dioxane and water. (0 (VII) x F R1~O M2 Process P5
[0119] The compounds of formula (VIII) may be commercially available or may be prepared from readily available compounds according to known procedures.
[0120] The compounds of formula (VII) can be prepared, according to process P6, from the compounds of formula (V), wherein W1 is a leaving group, such as bromine, for example, by halogen-metal exchange or by palladium-catalyzed borylation. Processes P6 and P5 can be combined into a single-step process. Petition 870260051039, dated 05 / 28 / 2026, page 46 / 314 43 / 149 XF (V) R1-0 W1 R1-0 F (VII) M2 Process P6
[0121] According to the invention, processes P1 to P6 can be carried out, if appropriate, in the presence of a solvent, and, if appropriate, in the presence of a base.
[0122] 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 optionally halogenated, aliphatic, alicyclic or aromatic hydrocarbons, 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.
[0123] Suitable bases for carrying out processes P1 to P6, according to the invention, are inorganic and organic bases that are commonly used for such reactions. Preference is given to the use of alkaline earth metal, alkali metal hydride, alkali metal hydroxides or alkali metal alkoxides, such as sodium hydroxide, sodium hydride, calcium hydroxide, potassium hydroxide, tert-butoxide of Petition 870260051039, dated 05 / 28 / 2026, page 47 / 314 44 / 149 potassium or other ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate and also tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, 1,4-diazabicyclo[2,2,2]octane (DABCO), 1,5-diazabicyclo[4,3,0]non-5-ene (DBN) or 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU).
[0124] When carrying out processes P1 to P6, according to the invention, the reaction temperature can be independently varied within a relatively wide range. In general, the processes, according to the invention, are carried out at temperatures between -20 °C and 160 °C.
[0125] 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.
[0126] The processing is carried out by conventional 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 conventional methods, such as chromatography or recrystallization, from any impurities that may still be present.
[0127] 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. Petition 870260051039, dated 05 / 28 / 2026, page 48 / 314 45 / 149
[0128] The aspects of the present teaching can be further understood in the light of the following examples, which should not be interpreted as limiting the scope of the present teaching in any way. Compositions and formulations
[0129] The present invention also 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.
[0130] 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.
[0131] A carrier is a solid or liquid substance, natural or synthetic, organic or inorganic, that is generally inert. The carrier generally improves 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 powders such as kaolin, clays, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, and synthetic rock powders such as finely divided silica, alumina, and silicates. Examples of solid carriers typically useful for preparing granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, and dolomite, synthetic granules of inorganic and organic powders, and granules of organic material such as paper, sawdust, coconut husks, corn cobs, and tobacco stalks.Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include polar and non-polar organic chemical liquids, for example, from the aromatic and non-aromatic hydrocarbon classes (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, alkylnaphthalenes, etc.). Petition 870260051039, dated 05 / 28 / 2026, page 49 / 314 46 / 149 aromatic or aliphatic chlorinated hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be 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 can also be a liquefied gaseous extender, that is, a liquid that is gaseous at standard temperature and under standard pressure, for example, aerosol propellants such as halohydrocarbons, butane, propane, nitrogen, and carbon dioxide.The amount of 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.
[0132] The composition may also comprise one or more acceptable auxiliaries that are usual for the formulation of compositions (e.g., agrochemical compositions), such as one or more surfactants.
[0133] The surfactant may be an ionic (cationic or anionic) or non-ionic surfactant, such as ionic or non-ionic emulsifiers, foam formers, dispersants, 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. Petition 870260051039, dated 05 / 28 / 2026, page 50 / 314 47 / 149 of compounds containing sulfates, sulfonates, phosphates (e.g., alkyl sulfonates, alkylsulfates, aryl sulfonates) and protein hydrolysates, residual liquors of lignosulfite and methylcellulose. 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 surfactants typically ranges from 5 to 40% by weight of the composition.
[0134] Other examples of auxiliaries that are commonly used in the formulation of agrochemical compositions include water repellents, siccants, binders (adhesive, bonding agent, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose), thickeners, stabilizers (e.g., cold stabilizers, preservatives, antioxidants, light stabilizers or other agents that improve chemical and / or physical stability), colorants or pigments (such as inorganic pigments, e.g., iron oxide, titanium oxide and Prussian Blue;organic colorants (e.g., alizarin, azo and metal phthalocyanine dyes), antifoaming agents (e.g., silicone and magnesium stearate antifoaming agents), preservatives (e.g., dichlorophene and benzyl alcohol hemiformal), 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 trace nutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts), protective colloids, thixotropic substances, penetrants, sequestering and complexing agents.
[0135] The choice of auxiliaries is related to the intended method of application of the compound of formula (I) and / or to the physical properties. In addition, the Petition 870260051039, dated 05 / 28 / 2026, page 51 / 314 48 / 149 auxiliary substances can be chosen to impart particular properties (technical, physical and / or biological properties) to the compositions or forms of use prepared from them. The choice of auxiliary substances can allow the customization of the compositions for specific needs.
[0136] The composition may be in any usual form, such as solutions (e.g., aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, dispersion 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.
[0137] 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 means of a suitable device, such as a spraying or dusting device. Alternatively, the composition may be supplied to the end user in the form of concentrates which must be diluted, preferably with water, before use.
[0138] The composition can be prepared in conventional ways, for example, by mixing compound formula (I) with one or more suitable auxiliaries, such as those disclosed in this report above.
[0139] 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).
[0140] The compounds and compositions comprising them may be mixed with other active ingredients, such as fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, regulators of Petition 870260051039, dated 05 / 28 / 2026, page 52 / 314 49 / 149 growth, plant protection agents or semiochemicals. This can broaden the spectrum of activity or prevent the development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are published in the Pesticide Manual, 17th Edition.
[0141] Examples of fungicides that can be mixed with the compounds of formula (I) and with the composition of the invention are: 1) Inibidores da biossíntese de ergosterol, por exemplo, (1,001) ciproconazol, (1.002) difenoconazol, (1.003) epoxiconazol, (1.004) fenexamida, (1.005) fenpropidina, (1.006) fenpropimorf, (1.007) fenpirazamina, (1.008) fluquinconazol, (1.009) flutriafol, (1.010) imazalil, (1.011) sulfato de imazalil, (1.012) ipconazol, (1.013) metconazol, (1.014) miclobutanil, (1.015) paclobutrazol, (1.016) procloraz, (1.017) propiconazol, (1.018) protioconazol, (1.019) pirisoxazol, (1.020) espiroxamina, (1.021) tebuconazol, (1.022) tetraconazol, (1.023) triadimenol, (1.024) tridemorf, (1.025) triticonazol, (1.026) (1R,2S,5S)-5-(4-clorobenzil)-2-(clorometil)-2metil-1 -(1 H-1,2,4-triazol-1 -ilmetil)ciclopentanol, (1.027) (1 S,2R,5R)-5-(4-clorobenzil)2-(clorometil)-2-metil-1 -(1 H-1,2,4-triazol-1 -ilmetil)ciclopentanol, (1.028) (2R)-2-(1clorociclopropil)-4-[(1 R)-2,2-diclorociclopropil]-1 -(1 H-1,2,4-triazol-1 -il)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1 -(1 H-1,2,4-triazol-1 yl)butan-2-ol, (1,030) (2R)-2-[4-(4-chlorophenoxy)-fluoromethyl-2-(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, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1 S)-2,2-dichlorocyclopropyl]-1 -(1 H-1,2,4-triazol-1 -yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-methyl-(phenyl-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, (1.037) 1 -({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy-4-methyl pethium)] 870260051039, of 28 / 05 / 2026, page 53 / 314. 50 / 149 1,3-dioxolan-2-yl}methyl)-1 H-1,2,4-triazole, (1.038) 1 -({(2S,4S)-2-[2-chloro-4-(4chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole (1.038). thiocyanate of 1 -{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazol-5-yl, (1,040) thiocyanate of 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H1,2,4-triazol-5-yl, (1,041) thiocyanate of 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazol-5-yla, (1.042) 2-[(2R,4R,5R)-1 -(2,4dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3-thiona, (1.043) 2-[(2R,4R,5S)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1,044) 2-[(2R,4S,5R)-1 -(2,4-dichlorophenyl)-5-hydroxy2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazole-3thiona, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1.047) 2,1[R,5R) -(2,4-dichlorophenyl)-5hydroxy-2,6,6-trimethyl-heptane-4-yl]-2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1,048) 2[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H1,2,4-triazol-3-thione, (1,049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1,050) 2-[1 -(2,4-dichlorophenyl)-5hydroxy-2,6,6-trimethyl-heptan-4-yl]-2,4-di-hydro-3H-1,2,4-triazol-3-thione, (1,051) 2-[2chloro-4-(2,4-dichlorophenoxy-1,1)phenyl -yl)propan-2-ol, (1,052) 2-[2-chloro4-(4-chlorophenoxy)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)butan-2-ol, (1,053) 2-[4-(4-chlorophenoxy(trifluoromethyl]-2)(trifluoromethyl) H-1,2,4-triazol-1 -yl)butan-2-ol, (1,054) 2-[4-(4-chlorophenoxy)-2(trifluoromethyl)phenyl]-1 -(1 H-1,2,4-triazol-1 -yl)pentan-2-ol, (1,05fluco056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-di-hydro-3H-1,2,4triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)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-thiona, (1.059) 5-(4chlorobenzyl)-2-(chloromethyl-1)-(1-1) H-1,2,4-triazole-1 -ylmethyl)ciclopentanol, (1.060). Petition 870260051039, of 28 / 05 / 2026, p. 54 / 314 51 / 149 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1 -{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4difluorophenyl)oxiran-2-yl]methyl}-1 H-1,2,4-triazole, (1.063) N'-(2,5-dimethyl-4-{[3-(1, 1,2,2tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N'-(2,5dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-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-N-methylimidoformamide, (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-[(2,2,3,3tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N'-(2,5dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.071) N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N'-(4-{[3(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N'-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methyl-formamide (1.07). N'-[5-bromo-6-(2,3-di-hydro-1 H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-Nmethylimidoformamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-Nethyl-N-methylimidoformamide, (1.076) N'-{5-bromo-6-[(1 R)-1 -(3,5-difluorophenyl)ethoxy]-2methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1,077) N'-{5-bromo-6-[(1S)-1-(3,5difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-methylimidoformamide, (1.078) N'-{5bromo-6-[(cis-4-isopropylcyclo-hexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-Nmethylimidoformamide, (1.079) N'-{5-bromo-6-[(trans-4-isopropylcyclo-hexyl)oxy]-2methylpyridine-3-yl}-N-ethyl-N-methylimidoformamide, (1,080) N'-{5-bromo-6-[1 -(3,5difluorophenyl)ethoxy]-2-methylpyridine-3-yl}-N-ethyl-N-methylimidoformamide, (1,081) ipfentrifluconazole, (1,082) 2-[4-(4-chlorophenoxy)-2-(trifluorophenyl)H-1,ão14-Pethyl) 870260051039, dated 5 / 28 / 2026, pp. 55 / 314. 52 / 149 triazol-1-yl)propan-2-ol, (1,083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1(1,2,4-triazol-1 -yl)propan-2-ol, (1,084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 (1,2,4-triazol-1 -yl)propan-2-ol, (1,085) 3-[2-(1 -chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazol-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-(2,2,2-1- hydroxy-1-phenylethyl)phenyl]-N-methylimidoformamide, (1,088) N'-{5-bromo-2-methyl-6-[(1propoxypropan-2-yl)oxy]pyridine-3-yl}-N-ethyl-N-methylimidoformamide, (1,089) penco1, hexa1, (1,091) fenbuconazole and (1,092) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]2-hydroxy-3-(1,2,4-triazol-1-yl)methyl propanoate. 2) Respiratory chain inhibitors in complex I or II, e.g., (2.001) benzovindiflupir, (2.002) bixaphene, (2.003) boscalid, (2.004) carboxine, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad (2.008) furametpir, (2.009) Isofetamide, (2.010) isopyrazam (antiepimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (antiepimeric enantiomer 1S,4R,9R), 1RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (non-epimeric enantiomer 1R,4SR,9SR), (2.015) isopirazam (synepimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syne-epimeric racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pidiflumethofen, (2.020) pidiflumetofen, (2.020) pidixalum, (2.021) sedaifnoid. (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-di-hydro-1H-inden-4-yl)-1Hpyrazol-4-carboxamide, (2,023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-hydro-1-4-yl-inden-4-yl H-pyrazole-4-carboxamide, (2024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1 H-inden-4-yl]-1 H-pyrazol-4-carboxamide, (2,025) 1 -methyl-3-(trifluoromethyl)-trifN-yl-[2-2' 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-1H-inden-4-yl)-1 H-pyrazol-4-carboxamide, (2,028). Petition 870260051039, dated 5 / 28 / 2026, p. 56 / 314 53 / 149 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) fluindapyr, (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-tetra-hidro-1,4metanonaftalen-5-il]-3-(difluorometil)-1-metil-1H-pirazol-4-carboxamida, (2.040) N[(1 S,4R)-9-(diclorometileno)-1,2,3,4-tetra-hidro-1,4-metanonaftalen-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-[2cloro-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-isopropilbenzil)-1-metil-1H-pirazol-4carboxamida, (2.047) N-ciclopropil-3-(difluorometil)-5-fluoro-N-(2-isopropil-5metilbenzil)-1 -metil-1 H-pirazol-4-carboxamida, (2.048) N-ciclopropil-3-(difluorometil)5-fluoro-N-(2-isopropilbenzil)-1 -metil-1 H-pirazol-4-carbotioamida, (2.049) Nciclopropil-3-(difluorometil)-5-fluoro-N-(2-isopropilbenzil)-1-metil-1H-pirazol-4. Petição 870260051039, de 28 / 05 / 2026, pág. 57 / 314 54 / 149 carboxamida, (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) pirapropona, (2.058) N-[rac-(1S,2S)-2(2,4-diclorofenil)ciclobutil]-2-(trifluorometil)nicotinamida, (2.059) N-[(1 S,2S)-2-(2,4diclorofenil)ciclobutil]-2-(trifluorometil)nicotinamida. 3) Respiratory chain inhibitors in complex III, for example, (3.001) ametoctradine, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumetoxystrobin, (3.005) coumoxystrobin, (3.006) ciazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) cresoxim-methyl, (3.014) metominostrobin, (3.015) orisastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyramethostrobin, (3.019) pyroxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2[({[(1 E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2(methoxy-imino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1 -(4-chlorophenyl)-1H-pyrazol-3yl]oxy}-2-(methoxy-imino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3,024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamide, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclo-hexyl)-3-formamido-2hydroxybenzamide, (3,028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1 H-pyrazol-3-yl]oxy}-2. Petition 870260051039, of 28 / 05 / 2026, p. 58 / 314 55 / 149 (methoxy-imino)-N,3-dimethylpent-3-enamide, (3.029) {5-[3-(2,4-dimethylphenyl)-1 H-pyrazol1-yl]-2-methylbenzyl}methyl carbamate, (3.030) methyltetraprole, (3.031) florxamid. 4) Inhibitors of mitosis and cell division, for example, (4.001) carbendazim, (4.002) dietofencarb, (4.003) etaboxam, (4.004) fluopicolida, (4.005) pencicuron, (4.006) thiabendazol, (4.007) thiophanate-methyla, (4.008) zoxamida, (4.009) pyridaclomethyla, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.025) N(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1 H-pyrazol-5-amine, (4.026) fluopimomida. 5) Compounds capable of having an action on multiple sites, for example, (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) Petition 870260051039, dated 05 / 28 / 2026, page 59 / 314 56 / 149 metiram zinc, (5.017) copper oxine, (5.018) propineb, (5.019) sulfur and sulfur preparations, including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]diti-yne[2,3c][1,2]thiazol-3-carbonitrile. 6) Compounds capable of inducing a host defense, for example, (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) thiadinil. 7) Inhibitors of the biosynthesis of amino acids and / or proteins, for example, (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline. 8) Inhibitors of ATP production, for example, (8.001) silthiofam. 9) Cell wall synthesis inhibitors, e.g. (9,001) bentiavalicarb, (9,002) dimetomorph, (9,003) flumorph, (9,004) iprovalicarb, (9,005) mandipropamid, (9,006) pyrimorph, (9,007) valifenalate, (9,008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one. 10) Lipid and membrane synthesis inhibitors, for example, (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl. 11) Inhibitors of melanin biosynthesis, for example, (11.001) tricyclazole, (11.002) tolprocarb. 12) Nucleic acid synthesis inhibitors, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (ciralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam). 13) Signal transduction inhibitors, for example, (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxifen, (13.006) vinclozolin. Petition 870260051039, dated 05 / 28 / 2026, page 60 / 314 57 / 149 14) Compounds capable of acting as an uncoupler, for example, (14.001) fluazinam, (14.002) meptildinocap. 15) Other fungicides selected from the group consisting of (15.001) abscisic acid, (15.002) bentiazole, (15.003) betoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) cufraneb, (15.008) ciflufenamid, (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) nitrothal-isopropyl, (15,021) oxamocarb, (15,022) oxathiapiproline, (15,023) oxyphenthy-in, (15,024) pentachlorophenol and salts, (15,025) phosphorous acid and its salts, (15,026) propamocarb-fosetylate, (15,027) pyriofenone (clazafenone), (15,028) tebufloquine, (15,029) teclophthalam, (15,030) tolnifanide, (15,031) 1 -(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-di-hydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine1 -yl)-2-[5-methyl-3,)(zoethyl-yl-1 Horomethyl-pyl (15,033) 2-(6-benzylpyridine-2yl)quinazoline, (15,034) dipimethitrone, (15,035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1yl]-1 -[4-(4-(in-{pro5-[2-2 -yloxy)phenyl]-4,5-di-hydro-1,2-oxazol-3-yl}-1,3-thiazol-2yl)piperidin-1 -yl]ethanone, (15,036) 2-[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl] -[4-(4-{5-[2chloro-6-(prop-2-in-1 -yloxy)phenyl]-4,5-di-hydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidine-1yl]ethanone, (15.037) -[3-methyl) H-pyrazol-1 -yl]-1 -[4-(4-{5-[2-fluoro-6(prop-2-in-1 -yloxy)phenyl]-4,5-di-hydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-03,8 (115.ethanone 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridine-2-yl]quinazoline, (15,039) methanosulfonate of 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1yl]acetyl}piperidine-4-yl)-1,3-thiazol-4-yl]-4,5-di-hydro-1,2-oxazol-5-chlorophenyl},1-3-040) methanosulfonate of 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-di-hydrophenyl}zol-1,3.-5-oi Petition 870260051039, dated 5 / 28 / 2026, p. 61 / 314 58 / 149 (15.041) ipflufenoquine, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3yl)óxi]phenyl}propan-2-ol, (15.043) fluoxapiproline, (15.044) methanesulfonate de 2-{3[2-(1-{[3,5-bis(difluoromethyl)-1 H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl, (15,045) 2-phenylphenol and sais, (15,046) 3-(4,4,5-trifluoro-3,3dimetil-3,4-di-hidroisoquinolin-1-il)quinolina, (15.047) quinofumelina, (15.048) 4amino-5-fluoropirimidin-2-ol (tautomeric form: 4-amino-5-fluoropirimidin-2(1H)ona), (15.049) ácido 4-oxo-4-[(2-feniletil)amino]butanoico, (15.050) 5-amino-1,3,4thiadiazol-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-in-1 -yl)thiophene-2-sulfonohidrazida, (15.052) 5-fluoro-2-[(4-fluorobenzyl)óxi]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4methylbenzyl)óxi]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) but-3-in-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5yl)(phenyl)methyleno]amino}óxy)metil]piridin-2-yl}carbamato, (15.056) (2Z)-3-amino-2cyano-3-phenylacrylato de ethyla, (15.057) ácido fenazino-1-carboxílico, (15.058) 3,4,5-trihidroxybenzoato de propyla, (15.059) quinolin-8-ol, (15.060) sulfato de quinolin-8-ol (2:1), (15.061) {6-[({[(1-metil-1 H-tetrazol-5-yl)(phenyl)methyleno]amino}óxi)metil]piridin-2il}carbamato de tert-butyla, (15.062) 5-fluoro-4-imino-3-metil-1-[(4-metilfenil)sulfonyl]3,4-di-hidropyrimidin-2(1H)-ona, (15.063) aminopirifen, (15.064) (N'-[2-cloro-4-(2fluorofenóxi)-5-metilfenil]-N-ethyl-N-metilimidoformamida), (15.065) (N'-(2-cloro-5-metil4-fenoxifenil)-N-ethyl-N-metilimidoformamida), (15.066) (2-{2-[(7,8-difluoro-2methylquinolin-3-yl)óxi]-6-fluorophenyl}propan-2-ol), (15.067) (5-bromo-1 -(5,6dimethylpyridin-3-yl)-3,3-dimethyl-3,4-di-hidroisoquinoline), (15.068) (3-(4,4-difluoro-5,5dimethyl-4,5-di-hidrothieno[2,3-c]pyridin-7-yl)quinoline), (15.069) (1-(4,5-dimethyl-1 Hbenzimidazol-1 -yl)-4,4-difluoro-3,3-dimethyl-3,4-di-hydroisoquinoline), (15,070) 8-fluoro3-(5-fluoro-3,3-dimethyl-quinone-1,4 (15,071) 8-fluoro-3-(5fluoro-3,3,4,4-tetramethyl-3,4-di-hydroisoquinolin-1-yl)quinolone, (15,072) 3-(4,4difluoro-3,3-dimethyl-3,4-diquino-8hydrofyl-quinoluene-hydroquinolone- (15,073) (N-methyl-Nphenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide), (15,074) {4-[5Petition 870260051039, dated 28 / 05 / 2026 62 / 314. 59 / 149 (trifluorometil)-1,2,4-oxadiazol-3-il]fenil}carbamato de metila, (15.075) (N-{4-[5(trifluorometil)-l ,2,4-oxadiazol-3-il]benzil}ciclopropanocarboxamida), (15.076) Nmetil-4-(5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.077) N-[(E)-metóxiiminometil]-4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.078) N-[(Z)metóxi-iminometil]-4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.079) N-[4[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]ciclopropanocarboxamida, (15.080) N-(2fluorofenil)-4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.081) 2,2-difluoroN-metil-2-[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]acetamida, (15.082) N-alil-N[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il)fenil]metil]acetamida, (15.083) N-[(E)-Nmetóxi-C-metil-carbonimidoil]-4-(5-(trifluorometil)-1,2,4-oxadiazol-3-il]benzamida, (15.084) N-[(Z)-N-metóxi-C-metil-carbonimidoil]-4-[5-(trifluorometil)-1,2,4-oxadiazol-3il]benzamida, (15.085) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoropropanamide, (15.090) 1-methoxy-1-methyl-3-[[4[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.091) 1,1 -diethyl-3-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)1,2,4-oxadiazol-3-yl]phenyl]methyl]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) Nmethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]propanamide, (15.098) 1 -methoxy-3-methyl-1 -[[4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 1,3-dimethoxy-1 -[[4-[5-(trifluoromethyl)-1,2,4Petição 870260051039, but 28 / 05 / 2026, p. 63 / 314. 60 / 149 oxadiazol-3-yl]phenyl]methyl]urea, (15.100) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3yl]phenyl]methyl]piperidin-2-one, (15.102) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4oxadiazol-3-yl]phenyl]methyl]iso-oxazolidin-3-one, (15.103) 5,5-dimethyl-2-[[4-[5(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.104) 3,3-dimethyl -[[4-[5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]piperidin-2-ona, (15.105) 1 -[[3 fluoro-4-(5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]azepan-2-ona, (15.106) 4,4 dimetil-2-[[4-(5-(trifluorometil)-1,2,4-oxadiazol-3-il]fenil]metil]isoxazolidin-3-ona, (15.107) 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-3-il]benzil}-1H-pirazol-4carboxilato 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)-1,2,4oxadiazol-3-il]benzil}butanamida, (15.111) N-(1-metilciclopropil)-4-[5-(trifluorometil)1,2,4-oxadiazol-3-il]benzamida, (15.112) N-(2,4-difluorofenil)-4-[5-(trifluorometil)1,2,4-oxadiazol-3-il]benzamida, (15.113) 1-(5,6-dimetilpiridin-3-il)-4,4-difluoro-3,3dimetil-3,4-di-hidroisoquinolina, (15.114) 1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115) 1 -(5-(fluoromethyl)-6-methyl-pyridin 3-yl)-4,4-difluoro-3,3-dimetil-3,4-di-hidroisoquinolina, (15.116) 1 -(6-(difluorometil)-5 methóxi-piridin-3-yl)-4,4-difluoro-3,3-dimetil-3,4-di-hidroisoquinolina, (15.117) 4-[5-(trifluorometil)-1,2,4-oxadiazol-3-yl]fenila dimetil carbamato, (15.118) N-{4-[5 (trifluorometil)-1,2,4-oxadiazol-3-yl]fenil}propanamida, (15.119) methanesulfonato de 3-[2-(1 -{[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl] 1,5-di-hydro-2,4-benzodioxepin-6-yl, (15,120) methanosulfonate of 9-fluoro-3-[2-(1 {[5-methyl-3-(trifluoromethyl)-1 H-pyrazol-1-yl]acetyl}piperizol-1,3-di-yl-yl] hydro-2,4-benzodioxepin-6-yl, (15,121) methanosulfonate of 3-[2-(1-{[3,5 bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperidine-4-yl)-1,3-thiazol-hydroyl-dio,2-di-6-yl]-ben (15,122) methanosulfonate of 3-[2-(1-{[3,5-bis(difluoromethyl)-1H Petition 870260051039, dated 5 / 28 / 2026, p. 64 / 314 61 / 149 pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin6-yl, (15,123) 1 -(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15,124) 8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2yl)quinoline-3-carboxamide, (15,125) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15,126) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8fluoroquinolino-3-carboxamide and (15,127) N-[(2S)-2,4-dimethyl-1-phenylpentan-2-yl]-8fluoroquinolino-3-carboxamide.
[0142] All named blending partners of classes (1) to (15), as described in this report above, may be present in the form of the free compound and / or, if their functional groups permit, an agriculturally acceptable salt thereof.
[0143] The compounds of formula (I) and compositions comprising them may be combined with one or more biological control agents.
[0144] Examples of biological control agents that can be combined with the compounds of formula (I) and compositions comprising them are: (a) Antibacterial agents selected from the group consisting of: (A1) bacteria, such as (A1.1) Bacillus subtilis, in particular, strain QST713 / AQ713 (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); (A1.2) 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); (A1.3) Bacillus pumilus, in particular, strain BU F-33 (with NRRL Accession No. 50185); (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available as Taegro® from Novozymes, US); (A1.5) a strain of Paenibacillus sp. with NRRL Accession No. B Petition 870260051039, dated 05 / 28 / 2026, page 65 / 314 62 / 149 50972 or Accession No. NRRL B-67129 and described in International Patent Publication No. WO 2016 / 154297; and (A2) fungi, such as (A2.1) Aureobasidium pullulans, in particular, blastospores of strain DSM14940; (A2.2) Aureobasidium pullulans blastospores of strain DSM 14941; (A2.3) Aureobasidium pullulans, in particular, mixtures of blastospores of strains DSM14940 and DSM14941; (B) Fungicides selected from the group consisting of: (B1) bacteria, for example, (B1.1) Bacillus subtilis, in particular, strain QST713 / AQ713 (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, strain QST2808 (available as SONATA® from Bayer CropScience LP, US, with NRRL Accession No. B-30087 and described in US Patent No. 6,245,551); (B1.3) Bacillus pumilus, in particular, strain GB34 (available as Yield Shield® from Bayer AG, DE); (B1.4) Bacillus pumilus, in particular, strain BU F-33 (with NRRL Accession No. 50185); (B1.5) Bacillus amyloliquefaciens, in particular, strain D747 (available as Double Nickel™ from Certis, US, with FERM Accession No. 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 Registrations Nos. 4764, 5454, 5096 and 5277); (B1.7) Bacillus amyloliquefaciens strain MBI 600 (available as SUBTILEX from BASF SE); (B1.8) Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, DE); (B1.9) Bacillus subtilis var. amyloliquefaciens strain 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. Petition 870260051039, dated 05 / 28 / 2026, p. 66 / 314 63 / 149 licheniformis, in particular, strain SB3086 (available as EcoGuard™ Biofungicide and Green Releaf from Novozymes); (B1.12) a strain of Paenibacillus sp. with NRRL Accession No. B-50972 or NRRL Accession No. B67129 and described in International Patent Publication No. WO 2016 / 154297.
[0145] In some embodiments, the biological control agent is a strain of Bacillus subtilis or Bacillus amyloliquefaciens that produces a fengicin- or plipastatin-like compound, an iturin-like compound and / or a surfactin-like compound. For basic 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 to 125. Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (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), Bacillus amyloliquefaciens strain D747 (available as Double Nickel™ from Certis, US, with FERM accession number BP-8234 and disclosed in US Patent No. 7,094,592); Bacillus subtilis MBI600 (available as SUBTILEX® from Becker Underwood, US EPA Reg.No. 71840 a 8); Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registrations Nos. 4764, 5454, 5096 and 5277); Bacillus amyloliquefaciens, in particular, 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 (B2) fungi, for example: (B2.1) Coniothyrium minitans, in particular, strain CON / M / 91-8 (DSM Accession No. 9660; for example, Contans® from Bayer); (B2.2) Metschnikowia fructicola, in particular, strain NRRL Y-30752 (by. Petition 870260051039, dated 05 / 28 / 2026, p. 67 / 314 64 / 149 example, Shemer®); (B2.3) Microsphaeropsis ochracea (e.g., Microx® from Prophyta); (B2.5) Trichoderma spp, including Trichoderma atroviride, strain SC1 described in International Application No. PCT / IT2008 / 000196); (B2.6) Trichoderma harzianum rifai strain KRL-AG2 (also known as strain T-22, / ATCC 208479, e.g., PLANTSHIELD T-22G, Rootshield®, and TurfShield from BioWorks, US); (B2.14) Gliocladium roseum, strain 321U from WF Stoneman Company LLC; (B2.35) Talaromyces flavus, strain V117b; (B2.36) Trichoderma asperellum, strain ICC 012 from Isagro; (B2.37) Trichoderma asperellum, strain SKT-1 (e.g., ECO-HOPE® from Kumiai Chemical Industry); (B2.38) Trichoderma atroviride, strain CNCM I-1237 (e.g., Esquive® WP from Agrauxine, FR); (B2.39) Trichoderma atroviride, strain No. V08 / 002387; (B2.40) Trichoderma atroviride, strain NMI No. V08 / 002388; (B2.41) Trichoderma atroviride, strain NMI No. V08 / 002389; (B2.42) Trichoderma atroviride, strain NMI No V08 / 002390; (B2.43) Trichoderma atroviride, strain LC52 (for example, Tenet by Agrimm Technologies Limited); (B2.44) Trichoderma atroviride, strain ATCC 20476 (IMI 206040); (B2.45) Trichoderma atroviride, strain T11 (IMI352941 / CECT20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (for example, Trichodex® from Makhteshim, US); (B2.49) Trichoderma harzianum, in particular, strain KD (for example, Trichoplus from Biological Control Products, SA (acquired by Becker Underwood)); (B2.50) Trichoderma harzianum, cepa ITEM 908 (por exemplo, Trianum-P a partir da Koppert); (B2.51) Trichoderma harzianum, cepa TH35 (por exemplo, Root-Pro por Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens), in particular, a cepa GL-21 (for example, SoilGard 12G por Certis, US); (B2.53) Trichoderma viride, cepa TV1 (por exemplo, Trianum-P por Koppert); (B2.54) Ampelomyces quisqualis, in particular, strain AQ 10 (e.g. AQ 10® by IntrachemBio Italia); (B2. 56) Aureobasidium pullulans, in particular, the blastospores of strain DSM14940; (B2. 57). Petition 870260051039, dated 05 / 28 / 2026, p. 68 / 314 65 / 149 Aureobasidium pullulans, in particular, the blastospores of strain DSM 14941; (B2.58) Aureobasidium pullulans, in particular, the mixtures of blastospores of strains DSM14940 and DSM 14941 (for example, 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 (for example, Prestop ® by AgBio Inc. and, also, for example, Primastop® by Kemira Agro Oy); (B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia of strain KV01 (e.g., Vertalec® by Koppert / Arysta); (B2.71) Penicillium vermiculatum; (B2.72) Anomalous Pichia, strain WRL-076 (NRRL Y-30842); (B2.75) Trichoderma atroviride , strain SKT-1 (FERM P-16510); (B2.76) Trichoderma atroviride , strain SKT-2 (FERM P16511); (B2.77) Trichoderma atroviride , strain SKT-3 (FERM P-17021); (B2.78) Trichoderma gamsii (formerly T .(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 by 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 the Trichoderma asperellum strain ICC 012 and the Trichoderma gamsii strain ICC 080 (product known, for example, as BIO-TAMTM from Bayer CropScience LP, US).
[0146] Other examples of biological control agents that can be combined with the compounds of formula (I) and compositions comprising them are: Petition 870260051039, dated 05 / 28 / 2026, p. 69 / 314 66 / 149 bacteria selected from the group consisting of Bacillus cereus, in particular, B. cereus strain CNCM I-1562 and Bacillus firmus, strain I-1582 (Accession No. CNCM I-1582), Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular, B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), B. thuringiensis subsp. aizawai, in particular, strain ABTS-1857 (SD-1372), B. thuringiensis subsp. kurstaki strain HD-1, B. thuringiensis subsp. tenebrionis cepa NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp (nematode Rotylenchulus reniformis)-PR3 (ATCC Accession No. SD-5834), Streptomyces microflavus cepa AQ6121 (= QRD 31.013, NRRL B50550) and Streptomyces galbus cepa AQ 6047 (NRRL Accession No. 30232); Selected fungi and yeasts from the group consisting of Beauveria bassiana, in particular, strain ATCC 74040, Lecanicillium spp, in particular, strain HRO LEC 12, Metarhizium anisopliae, in particular, strain F52 (DSM3884 or ATCC 90448), Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particular, strain IFPC 200613 or strain Apopka 97 (ATCC Accession No. 20874) and Paecilomyces lilacinus, in particular, P. lilacinus strain 251 (AGAL 89 / 030550); Selected viruses from the group consisting of Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydia pomonella (apple moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (sugar beet) mNPV, Spodoptera frugiperda (fall armyworm) mNPV and Spodoptera littoralis (African cotton bollworm) NPV. Bacteria and fungi that can be added as 'inoculants' to plants or plant parts or organs and which, by virtue of their particular properties, promote plant growth and plant health. Examples include: Agrobacterium spp, Azorhizobium caulinodans, Azospirillum spp, Azotobacter spp, Bradyrhizobium spp., Burkholderia spp., in particular, Burkholderia cepacia. Petition 870260051039, dated 05 / 28 / 2026, page 70 / 314 67 / 149 (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular, Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp. and Streptomyces spp. plant extracts and products formed by microorganisms, including proteins and secondary metabolites that can be used as biological control agents, such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, 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 / ryanodina, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrina, Viscum album, Brassicaceae extract, In particular, rapeseed powder or mustard powder.
[0147] Examples of insecticides, acaricides and nematicides, respectively, that can be mixed with the compounds of formula (I) and compositions comprising them are: (1) Acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, for example, alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, etiofencarb, fenobucarb, formetanate, furatiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimetacarb, XMC and xylylcarb; or organophosphates, for example, acephate, azamethifos, azinphos-ethyl, azinphosmethyl, cadusafos, chloridexifos, chlorfenvinfos, chlormefos, chlorpyrifos-methyl, coumafos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotofos, dimethoate, dimethylvinfos, disulfoton, EPN, ethion, etoprofos, famfur, fenamifos, fenitrothion, fenthion, Petition 870260051039, dated 05 / 28 / 2026, page 71 / 314 68 / 149 fostiazate, heptenofos, imiciafos, isofenfos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxation, malathion, mecarbam, methamidofos, metidation, mevinfos, monocrotofos, naled, ometoate, oxidemeton-methyl, parathion-methyl, fentoate, forate, fosalone, phosmet, phosfamidon, foxim, pirimifos-methyl, profenofos, propetanfos, protiofos, piraclofos, piridafenthion, quinalfos, sulfotep, tebupirimfos, temefos, terbufos, tetrachlorvinfos, thiometon, triazofos, trichlorfon and vamidothion. (2) GABA-activated chloride channel blockers, such as, for example, cyclodiene-organochlorines, for example, chlordane and endosulfan or phenylpyrazoles (fiprols), for example, etiprol and fipronil. (3) Sodium channel modulators, such as, for example, pyrethroids, for example, 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, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadethrin, monofluorothrin, permethrin, phenothrin [trans isomer (1R)], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer)], tralomethrin and transfluthrin or DDT or methoxychlor. (4) Competitive modulators of the nicotinic acetylcholine receptor (nAChR), such as, for example, neonicotinoids, for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupiradifurone. (5) Allosteric modulators of the nicotinic acetylcholine receptor (nAChR), such as, for example, spinosyns, for example, spinotoram and spinosad. Petition 870260051039, dated 05 / 28 / 2026, page 72 / 314 69 / 149 (6) Allosteric modulators of the glutamate-activated chloride channel (GluCl), such as, for example, avermectins / milbemycins, for example, abamectin, emamectin benzoate, lepimectin and milbemectin. (7) Mimics of juvenile hormone, such as, for example, analogues of juvenile hormone, for example, hydroprene, cynoprene and methoprene or fenoxycarb or pyriproxyfen. (8) Various non-specific inhibitors (multiple sites), such as, for example, alkyl halides, for example, methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic generators or methyl isocyanate, for example, diazomet and metam. (9) Modulators of chordotonal organs, such as, for example, pimetrozine or flonicamid. (10) Inhibitors of mite growth, such as, for example, clofentezine, hexthiazox and diflovidazine or ethoxazole. (11) Microbial disruptors of the insect intestinal membrane, such as, for example, Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and Bt plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1. (12) Mitochondrial ATP synthase inhibitors, such as ATP disruptors, such as, for example, diafenthiuron or organotin compounds, for example, azocyclotin, cyexatin and fenbutatin oxide or propargite or tetradifon. (13) Uncouplers of oxidative phosphorylation via disruption of the proton gradient, such as, for example, chlorfenapyr, DNOC and sulfluramid. (14) Nicotinic acetylcholine receptor channel blockers, such as, for example, bensultrap, cartap hydrochloride, tiocilam and tiosultrap-sodium. Petition 870260051039, dated 05 / 28 / 2026, page 73 / 314 70 / 149 (15) Chitin biosynthesis inhibitors, type 0, such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron. (16) Inhibitors of chitin biosynthesis, type 1, for example, buprofezin. (17) Molt disruptor (in particular, for Diptera, i.e., dipterans), such as, for example, cyromazine. (18) Ecdysone receptor agonists, such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide. (19) Octopamine receptor agonists, such as, for example, amitraz. (20) Inhibitors of mitochondrial complex III electron transport, such as, for example, hydramethylnon or acequinocil or fluacripyrim. (21) Inhibitors of mitochondrial complex I electron transport, such as, for example, from the METI acaricide group, for example, phenazaquin, fenpyroximate, pirimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris). (22) Voltage-dependent sodium channel blockers, such as, for example, indoxacarb or metaflumizone. (23) Acetyl CoA carboxylase inhibitors, such as, for example, tetronic and tetramic acid derivatives, for example, spirodiclofen, spiromesifen and spirotetramat. (24) Inhibitors of mitochondrial complex IV electron transport, such as, for example, phosphines, for example, aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, for example, calcium cyanide, potassium cyanide and sodium cyanide. (25) Inhibitors of mitochondrial complex II electron transport, such as, for example, beta-ketonitrile derivatives, for example, cyenopyrafene and cyflumethofen and carboxanilides, such as, for example, piflubumide. Petition 870260051039, dated 05 / 28 / 2026, page 74 / 314 71 / 149 (28) Ryanodine receptor modulators, such as, for example, diamides, for example, chlorantraniliprole, cyantraniliprole and flubendiamide, other active compounds, such as, for example, afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chlorprolethrin, cryolite, cyclaniliprol, cycloxapride, cylalodiamide, dichlormomethiothiaz, dicofol, epsilon-methofluthrin, epsilon-monfluthrin, flomethoquine, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprol, fluhexafon, fluopiram, fluralaner, fluxamethamide, fufenozide, guadipir, heptafluthrin, imidaclothiaz, Iprodione, kappa-bifenthrin, kappa-tefluthrin, lotilaner, meperfluthrin, paichongding, pyridalil, pirifluquinazone, piriminostrobin, spirobudiclofen, tetramethylfluthrin, tetratraniliprole, tetrachlorantraniliprole, tigolaner, thioxazafen, thiofluoximate, triflumezopyrim and iodomethane; in addition, preparations based on Bacillus firmus (I-1582, BioNeem,Votive), and also the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO 2006 / 043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4yl)methanone (known from WO 2003 / 106457) (CAS 637360-23-7), 2-chloro-N[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4(trifluoromethyl)phenyl]isonicotinamide (known from WO 2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4,5]dec3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), carbonate 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4,5]dec-3-en-4-yl ethyl (known from EP 2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160) (CAS 792914-58-0),PF1364 (known from JP 2010 / 018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO 2012 / 029672) (CAS 1363400-41-2), (3E)-3-[1-[(6-chloro-3-Petition 870260051039, dated 05 / 28 / 2026, page 75 / 314, 72 / 149 pyridyl)methyl]-2-pyridylideno]-1,1,1-trifluoro-propan-2-one (according to WO 2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-carboxamida (according to WO 2010 / 051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazol-3-carboxamida (contained starting from CN 103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-di-hidro-5(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(c / s-1-oxido-3-thiethanyl)-benzamida, 4-[5-(3,5dichlorophenyl)-4,5-di-hidro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-óxido-3thiethanyl)-benzamida and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-di-hidro-5-(trifluoromethyl)-3isoxazolyl]-2-methyl-N-(c / s-1-oxido-3-thietanyl)benzamida (confirmed starting from WO 2013 / 050317 A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-Netyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide,(+)-N-[3-chloro-1-(3-pyridinyl)-1Hpyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide and (-)-N-[3-chloro-1-(3pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide (known from 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 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 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, 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 WO 2011 / 085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4Petition 870260051039, of 05 / 28 / 2026, page 76 / 314 73 / 149 cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethyllidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinocarboxamide (known from CN 101715774 A) (CAS 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylcyclopropanecarboxylic acid ester (known from CN 103524422 A) (CAS 1542271-464); methyl ester of (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazino-4a(3H)carboxylic acid (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3O-ethyl-2,4-di-O-methyl-, 1 -[N-[4-[1 -[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1 H-1,2,4-triazol3-yl]phenyl]carbamate]-α-L-mannopyranose (known from US 2014 / 0275503 A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-aza-bicyclo[3,2,1]octane (CAS 1253850-56-4), (8-ant / )-8-(2cyclopropylmethoxy-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 WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-668), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide (known from WO 2015 / 058021 A1, 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 CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from WO 2013 / 115391 A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1 -methyl-1,8-diazaespiro[4,5]dec-3-en-2-one (known from WO 2010 / 066780 A1, WO 2011 / 151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaespiro[4,5]decane-2,4-dione (known from WO 2014 / 187846 A1) (CAS 1638765-58-8), ethyl ester of 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2oxo-1,8-diazaspiro[4,5]dec-3-en-4-yl-carbonic acid (known from WO, Petition 870260051039, dated 05 / 28 / 2026, page 77 / 314 74 / 149 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 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 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-[2propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3,3,1]nonane (known from WO 2011 / 105506 A1, WO 2016 / 133011 A1) (CAS 1332838-17-1). Examples of plant protection agents that can be mixed with the compounds of formula (I) and compositions comprising them are, for example, benoxacor, cloquintocet (-mexil), ciometrinil, cyprosulfamide, dichlormid, fenclorazol (-ethyl), fenclorim, flurazol, fluxofenim, furilazol, isoxadifen (-ethyl), mefenpir (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4azaespiro[4,5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).
[0148] Examples of herbicides that can be mixed with the compounds of formula (I) and compositions comprising them are:
[0149] Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, alidochlor, aloxidim, aloxidim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrol, ammonium sulfamate, anilophos, asulam, atrazine, azaphenidine, azimsulfuron, beflubutamid, benazoline, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclone, benzofenap, bicyclopyron, Bifenox, bilanafos, bilanafos-sodium, bispiribac, bisspiribac-sodium, Petition 870260051039, dated 05 / 28 / 2026, page 78 / 314 75 / 149 bromacil, bromobutide, bromophenoxim, bromoxynil, bromoxynyl-butyrate, -potassium, heptanoate, and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenaclor, butralin, butroxydim, butylate, cafenstrol, carbetamide, carfentrazone, carfentrazoneethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylline, cinosulfuron, clacifos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopiralid, cloransulam, cloransulam-methyl, cumiluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxidim, cialofop, cialofop-butyl, ciprazine, 2,4-D, 2,4-D-butyl, -butyl, -dimethylammonium, -diolamine, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolamine, and -trolamine, 2,4-DB, 2,4DB-butyl, -dimethylammonium, -iso-octyl,-potassium, and -sodium, daimuron (dimron), dalapon, dazomet, n-decanol, desmedifam, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzil)-4,4-dimethyl-1,2-oxazolidin-3-ona, 2-(2,5-dichlorobenzil)4,4-dimethyl-1,2-oxazolidin-3-ona, dichlorprop, dichlorprop-P, diclofop, diclofop-methyla, diclofop-P-methyla, diclosulam, difenzoquat, diflufenican, diflufenzopir, diflufenzopirsódico, dimefuron, dimepiperate, dimetachlor, dimetamethrin, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, difenamid, diquat, diquat-dibromid, dithiopir, diuron, DNOC, endothal, EPTC, esprocarb, etalfluralin, etamethsulfuron, etamethsulfuron-methyla, ethiozin, ethofumesate, etoxifen, etoxifen-ethyl, etoxissulfuron, etobenzanid, F-9600, F-5231, histo é, N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo4,5-di-hidro-1H-tetrazol-1-yl]phenyl}ethanesulfonamida, F-7967, histo é, 3-[7-chloro-5fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidino2,4(1H,3H)-diona, fenoxaprop,fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, phenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin Petition 870260051039, dated 05 / 28 / 2026, page 79 / 314 76 / 149 flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycophen, fluoroglycophen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methylsodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, flutiacet, flutiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, sodium, and -trimesium, H-9201, that is, O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxifop, haloxifop-P, haloxifop-ethoxyethyl, haloxifop-P-ethoxyethyl, haloxifop-methyl, haloxifop-P-methyl, hexazinone, HW-02, that is, 1-(dimethoxyphosphoryl)ethyl-(2,4-dichlorophenoxy)acetate, imazametabenz,imazametabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxinil, ioxiniloctanoate, -potassium and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutol, carbutilate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, cetospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotil, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium, and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotil, mecoprop-P, mecoprop-P-butotil, dimethylammonium, -2-ethylhexyl, and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, metabenzthiazuron, metam, metamifop, metamitron, metazaclor, metazosulfuron, metabenzthiazuron, methiopyrsulfuron, methiozoline,methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, methoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e., N-(3-chloro-4-isopropylphenyl)-2, Petition 870260051039, dated 05 / 28 / 2026, page 80 / 314 77 / 149 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, pentachlorphenol, pentoxazone, petoxamid, petroleum oils, fenmedifam, picloram, picolinafen, pinoxaden, piperofos, pretilaclor, primisulfuron, primisulfuron-methyl, prodiamine, profoxidim, prometon, promethrin, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxifen, piribambenz, piribambenz-isopropyl, piribambenzpropyl, pyribenzoxim,piributycarb, piridafol, piridato, piriftalid, piriminobac, piriminobac-metila, pirimisulfan, piritiobac, piritiobac-sódico, piroxassulfon, piroxsulam, quinclorac, quinmerac, quinoclamina, quizalofop, quizalofop-etila, quizalofop-P, quizalofop-P-etila, quizalofop-P-tefurila, rimsulfuron, saflufenacil, setoxidim, siduron, simazina, simetrin, SL-261, sulcotrion, sulfentrazona, sulfometuron, sulfometuron-metila, sulfossulfuron, SYN-523, SYP-249, isto é, 5-[2-cloro4-(trifluorometil)fenóxi]-2-nitrobenzoato de 1-etóxi-3-metil-1-oxobut-3-en-2-ila, SYP300, isto é, 1-[7-fluoro-3-oxo-4-(prop-2-in-1-il)-3,4-di-hidro-2H-1,4-benzoxazin-6-il]-3propil-2-tioxoimidazolidine-4,5-diona, 2,3,6-TBA, TCA (ácido tricloroacetico), TCAsódico, tebutiuron, tefuriltriona, tembotriona, tepraloxidim, terbacil, terbucarb, terbumeton, terbutilazine, terbutrin, tenilclor, tiazopir, tiencarbazona, thiencarbazonamethyla, thifensulfuron, thifensulfuron-methyla, thiobencarb, thiafenacil, tolpiralate, topramezona, tralcoxidim,triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triethazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazine, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, sulfate, Petition 870260051039, dated 05 / 28 / 2026, page 81 / 314 78 / 149 of urea, vernolate, XDE-848, ZJ-0862, that is, 3,4-dichloro-N-{2-[(4,6dimethoxypyrimidin-2-yl)oxy]benzyl}aniline and the following compounds:
[0150] Examples for plant growth regulators are:
[0151] Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancimidol, 6-benzylaminopurine, Brassinolid, catechin, chlormequat chloride, chlorprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dicegulac, dicegulac-sodium, endotal, endotal-dipotassium, -disodium and -mono(N,N-dimethylalkylammonium), ethephon, flumetraline, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, paclobutrazol, N-(2-phenylethyl)-beta-alanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P. Methods and uses
[0152] The compounds of formula (I) and the compositions comprising them have potent microbicidal activity. They can be used for the Petition 870260051039, dated 05 / 28 / 2026, page 82 / 314 79 / 149 control of unwanted microorganisms, such as unwanted fungi and bacteria. They can be particularly useful in crop protection (they control microorganisms that cause plant diseases) or to protect materials (e.g., industrial materials, wood, storage articles), as described in more detail in this report below. More specifically, the compounds of formula (I) and compositions comprising them can be used to protect seeds, germinating seeds, emerged seedlings, plants, plant parts, fruits, harvest articles and / or the soil in which the plants grow from unwanted microorganisms.
[0153] Control or control, as used in this report, 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 report below, these phytopathogenic microorganisms are the causal agents of a wide spectrum of plant diseases.
[0154] More specifically, the compounds of formula (I) and compositions comprising them can be used as fungicides. For the purpose of this descriptive report, the term “fungicide” refers to a compound or composition that can be used in crop protection for the control of 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).
[0155] The present invention also relates to a method for controlling unwanted microorganisms, such as phytopathogenic fungi, oomycetes and Petition 870260051039, dated 05 / 28 / 2026, page 83 / 314 80 / 149 bacteria, comprising the step of applying at least one compound of formula (I) or at least one 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).
[0156] Typically, when the compound and composition of the invention are used in curative or protective methods for the control of phytopathogenic fungi and / or phytopathogenic oomycetes, an effective and plant-compatible amount 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 to grow plants 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 beads. Effective and plant-compatible amount means an amount 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 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 experiments that are within the capabilities of a person skilled in the art. Plants and plant parts
[0157] The compounds of formula (I) and the compositions comprising them may be applied to any plants or parts of plants.
[0158] Plants means all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants that Petition 870260051039, dated 05 / 28 / 2026, page 84 / 314 81 / 149 can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including genetically modified plants (GMOs or transgenic plants) and plant cultivars that are protectable and unprotectable by plant breeding rights.
[0159] Plant parts are understood to be all parts and organs of plants above and below ground, such as shoots, leaves, flowers and roots, examples of which include leaves, needles, stems, trunks, flowers, fruiting bodies, fruits and seeds, and also roots, tubers and rhizomes. Plant parts also include harvested material and vegetative and generative propagation material, for example, cuttings, tubers, rhizomes, seedlings and seeds.
[0160] The 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 trees and plantations), Rubiaceae sp. (for example, coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example, lemons, oranges and grapefruits); 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 crop plants such as Gramineae sp.(e.g., corn, 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). Petition 870260051039, dated 05 / 28 / 2026, p. 85 / 314 82 / 149 mustard, horseradish and watercress), Fabaceae sp. (e.g., beans, peanuts), Papilionaceae sp. (e.g., soybeans), Solanaceae sp. (e.g., potatoes), Chenopodiaceae sp. (e.g., sugar beet, fodder beet, Swiss chard, beet); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.
[0161] In some preferred embodiments, wild plant species and plant cultivars, or those obtained by conventional biological reproduction methods, such as crossing or fusion of protoplasts, and also parts thereof, are treated in accordance with the methods of the invention.
[0162] 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. Plant cultivars are understood to be plants that have new properties (“traits”) and have been obtained by conventional breeding, mutagenesis or recombinant DNA techniques. They may be cultivars, varieties, bio- or genotypes.
[0163] The methods, according to the invention, can be used in the treatment of genetically modified organisms (GMOs), for example, plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The expression “heterologous gene” essentially means a gene that is supplied or constructed outside the plant and, when introduced into the nuclear, chloroplast or mitochondrial genome, provides the transformed plant with new or improved agronomic or other properties through the expression of a protein or polypeptide of Petition 870260051039, dated 05 / 28 / 2026, page 86 / 314 83 / 149 interest or through the downregulation or silencing of other genes that are present in the plant (using, for example, antisense technology, co-suppression technology, RNA interference - RNAi - technology or microRNA - miRNA technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.
[0164] Plants and plant cultivars that can be treated by the methods disclosed above include all plants that have genetic material that imparts particularly advantageous and useful traits to these plants (if obtained through reproduction and / or biotechnological means).
[0165] 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.
[0166] Plants and plant cultivars that can be treated by the methods disclosed above include those plants that are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, exposure to cold temperatures, exposure to heat, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.
[0167] Plants and plant cultivars that can be treated by the methods disclosed above include those plants characterized by increased yield characteristics. Increased yield in said plants may be the result, for example, of improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, Petition 870260051039, dated 05 / 28 / 2026, page 87 / 314 84 / 149 improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency, and accelerated maturation. Yield, moreover, can be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to early flowering, flowering control for hybrid seed production, seedling vigor, plant size, number and distance of internodes, root growth, seed size, fruit size, pod size, number of pods or ears, number of seeds per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence, and lodging resistance.Other yield traits 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.
[0168] 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 results in generally higher yield, vigor, health and resistance to biotic and abiotic stresses.
[0169] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that are herbicide-tolerant plants, that is, plants that become tolerant to one or more supplied herbicides. Such plants can be obtained by genetic transformation or by selecting plants containing a mutation that imparts such herbicide tolerance. Petition 870260051039, dated 05 / 28 / 2026, page 88 / 314 85 / 149
[0170] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that are insect-resistant transgenic plants, that is, plants that become resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selecting plants containing a mutation that imparts such resistance to the insect.
[0171] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars that are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation or by selecting plants containing a mutation that imparts such stress resistance.
[0172] 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.
[0173] 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 selecting plants that contain a mutation that communicates such altered fiber characteristics.
[0174] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated Petition 870260051039, dated 05 / 28 / 2026, page 89 / 314 86 / 149 by the methods disclosed above include plants and plant cultivars, such as rapeseed or related Brassica plants, with altered oil profile characteristics. Such plants may be obtained by genetic transformation or by selecting plants that contain a mutation that imparts such altered oil profile characteristics.
[0175] Plants and plant cultivars (obtained by plant biotechnology methods, such as genetic engineering) that can be treated by the methods disclosed above include plants and plant cultivars, such as rapeseed or related Brassica plants, with altered seed-breaking characteristics. Such plants can be obtained by genetic transformation or by selecting plants that contain a mutation that communicates such altered seed-breaking characteristics and include plants, such as rapeseed plants, with delayed or reduced seed-breaking.
[0176] 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
[0177] The methods disclosed above can be used to control microorganisms, in particular, phytopathogenic microorganisms, such as phytopathogenic fungi that cause diseases, such as: Diseases caused by powdery mildew pathogens, such as Blumeria species (e.g., Blumeria graminis), Podosphaera species (e.g., Podosphaera leucotricha), Sphaerotheca species (e.g., Sphaerotheca fuliginea), and Uncinula species (e.g., Uncinula necator); Petition 870260051039, dated 05 / 28 / 2026, page 90 / 314 87 / 149 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); Diseases caused by pathogens from the Oomycetes group, such as Albugo species (e.g., Albugo candida), Bremia species (e.g., Bremia lactucae), Peronospora species (e.g., Peronospora pisi or P. brassicae), Phytoftora species (e.g., Phytoftora infestans), Plasmopara species (e.g., Plasmopara viticola), Pseudoperonospora species (e.g., Pseudoperonospora humuli or Pseudoperonospora cubensis), and Pythium species (e.g., Pythium ultimum); Leaf spot diseases and leaf wilt diseases caused, for example, by Alternaria species (e.g., Alternaria solani), Cercospora species (e.g., Cercospora beticola), Cladiosporium species (e.g., Cladiosporium cucumerinum), Cochliobolus species (e.g., Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus), Colletotrichum species (e.g., Colletotrichum lindemuthanium), Cycloconium species (e.g., Cycloconium oleaginum), 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, Petition 870260051039, dated 05 / 28 / 2026, p. 91 / 314 88 / 149 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), root and stem diseases caused, for example, by Corticium species (e.g., Corticium graminearum), Fusarium species (e.g., Fusarium oxysporum), Gaeumannomyces species, (e.g., Gaeumannomyces graminis), Plasmodiophora species, (e.g., Plasmodiophora brassicae),species of Rhizoctonia, (e.g., Rhizoctonia solani), species of Sarocladium, (e.g., Sarocladium oryzae), species of Sclerotium, (e.g., Sclerotium oryzae), species of Tapesia, (e.g., Tapesia acuformis), species of Thielaviopsis, (e.g., Thielaviopsis basicola); Diseases of the ear and panicle (including corn ears) caused, for example, by Alternaria species (e.g., Alternaria spp.), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium cladosporioides), Claviceps species (e.g., Claviceps purpurea), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Monographella species (e.g., Monographella nivalis), and Stagnospora species (e.g., Stagnospora nodorum); diseases caused by smut fungi, for example, species of Sphacelotheca (e.g., Sphacelotheca reiliana), species of Tilletia (e.g., Petition 870260051039, dated 05 / 28 / 2026, page 92 / 314 89 / 149 example, Tilletia caries or Tilletia controversa), Urocystis species (e.g., Urocystis occulta), Ustilago species (e.g., Ustilago nuda); Fruit rot caused, for example, by Aspergillus species (e.g., Aspergillus flavus), Botrytis species (e.g., Botrytis cinerea), Penicillium species (e.g., Penicillium expansum or Penicillium purpurogenum), Rhizopus species (e.g., Rhizopus stolonifer), Sclerotinia species (e.g., Sclerotinia sclerotiorum), Verticillium species (e.g., Verticillium alboatrum); Diseases of rot and wilt transmitted by seeds and soil, and also diseases of seedlings caused, for example, by Alternaria species (e.g., Alternaria brassicicola), Aphanomyces species (e.g., Aphanomyces euteiches), Ascochyta species (e.g., Ascochyta lentis), Aspergillus species (e.g., Aspergillus flavus), Cladosporium species (e.g., Cladosporium herbarum), Cochliobolus species (e.g., Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium)), Colletotrichum species (e.g., Colletotrichum coccodes), Fusarium species (e.g., Fusarium culmorum), Gibberella species (e.g., Gibberella zeae), Macrophomina species (e.g., Macrophomina phaseolina), Microdochium species (e.g., Microdochium nivale), Monographella species (e.g. Monographella nivalis), Penicillium species (e.g. Penicillium expansum),species of Phoma (e.g., Phoma lingam), species of Phomopsis (e.g., Phomopsis sojae), species of Phytoftora (e.g., Phytoftora cactorum), species of Pyrenophora (e.g., Pyrenophora graminea), species of Piricularia (e.g., Piricularia oryzae), species of Pythium (e.g., Pythium ultimum), species of Rhizoctonia (e.g., Rhizoctonia solani), species of Rhizopus (e.g., Rhizopus oryzae), species of Sclerotium (e.g., Sclerotium rolfsii), species, Petition 870260051039, dated 05 / 28 / 2026, page 93 / 314 90 / 149 of Septoria (e.g., Septoria nodorum), species of Typhula (e.g., Typhula incarnate), species of Verticillium (e.g., Verticillium dahlia); Cancers, galls, and witches' brooms caused, for example, by species of Nectria (e.g., Nectria galligena); Wilt diseases caused, for example, by Monilinia species (e.g., Monilinia laxa); Deformities of leaves, flowers and fruits caused, for example, by Exobasidium species (e.g., Exobasidium vexans), Taphrina species (e.g., Taphrina deformans); Degenerative diseases in woody plants caused, for example, by species of Esca (e.g., Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea), species of Ganoderma (e.g., Ganoderma boninense); Diseases of flowers and seeds caused, for example, by Botrytis species (e.g., Botrytis cinerea); Plant tuber diseases caused, for example, by Rhizoctonia species (e.g., Rhizoctonia solani), Helminthosporium species (e.g., Helminthosporium solani); Diseases caused by bacterial pathogens, for example, Xanthomonas species (e.g., Xanthomonas campestris pv. oryzae), Pseudomonas species (e.g., Pseudomonas syringae pv. lachrymans), Erwinia species (e.g., Erwinia amylovora).
[0178] In particular, compounds of formula (I) and compositions comprising them are effective in controlling phytopathogenic fungi that cause rust diseases. Seed treatment Petition 870260051039, dated 05 / 28 / 2026, page 94 / 314 91 / 149
[0179] The method for controlling unwanted microorganisms can be used to protect seeds from phytopathogenic microorganisms, such as fungi.
[0180] The term “seeds”, as used in this report, includes dormant seed, prepared seed, pre-germinated seed and seed with emerged roots and leaves.
[0181] Thus, the present invention also relates to a method for protecting seeds and / or 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 the seeds with the compounds of formula (I) or a composition comprising the same not only protects the seeds from phytopathogenic microorganisms, but also the germinating plants, the emerged seedlings and the plants after emergence.
[0182] Seed treatment can be carried out before sowing, at the time of sowing or immediately afterwards.
[0183] When seed treatment is carried out before sowing (for example, so-called seed applications), seed treatment may be carried out as follows: the seeds may be placed in a mixer with a desired quantity of compounds of formula (I) or of a composition comprising the same (as such or after dilution), the seeds and the compounds of formula (I) or the composition comprising the same are mixed until a homogeneous distribution on the seeds is obtained. If appropriate, the seeds may then be dried.
[0184] The invention also relates to seeds treated with one or more compounds of formula (I) or a composition comprising them. As stated before, the use of treated seeds allows not only the protection of Petition 870260051039, dated 05 / 28 / 2026, p. 95 / 314 92 / 149 seeds before and after sowing against unwanted microorganisms, such as phytopathogenic fungi, but also allows the protection of germinating plants and young seedlings that emerge from said treated seeds. A large part of the damage to crop 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 shoots of the growing plant are particularly sensitive and even small damage can result in the death of the plant.
[0185] Therefore, the present invention also relates to a method for protecting seeds, germinating plants and emerged seedlings, more generally, to a method for protecting the crop from phytopathogenic microorganisms, comprising the step of using seeds treated with one or more compounds of formula (I) or a composition comprising the same.
[0186] Preferably, the seed is treated in a state where it is sufficiently stable so that no damage occurs during the course of treatment. In general, seeds can be treated at any time between harvest and shortly after sowing. It is common to use seeds that have been separated from the plant and freed from the ears, husks, stems, coverings, hairs or fruit pulp. For example, it is possible to use seeds that have been harvested, cleaned and dried with a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds that, after drying, for example, have been treated with water and then dried again, or seeds shortly after preparation, or seeds stored in prepared conditions, or pre-germinated seeds, or seeds sown in nursery trays, ribbons or paper.
[0187] The amount of compounds of formula (I) or composition comprising the same applied to the seed is typically such that seed germination is not impaired or the resulting plant is not damaged. This Petition 870260051039, dated 05 / 28 / 2026, page 96 / 314 93 / 149 must be ensured particularly in the case of the active ingredients exhibiting phytotoxic effects at certain application rates. The intrinsic phenotypes of transgenic plants must also be taken into account when determining the amount of compounds of formula (I) or composition comprising the same that will be applied to the seed, in order to obtain the ideal seed and protection of the germinating plant with a minimum amount of compounds of formula (I) or composition comprising the same used.
[0188] As indicated above, the compounds of formula (I) can 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) can be applied. Preferably, the compositions are applied to the seed in any suitable form. Examples of suitable formulations include solutions, emulsions, suspensions, powders, foams, fluid 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.
[0189] These formulations are prepared in a known manner, for example, by mixing the active ingredient or mixing it with usual additives, for example, usual extenders and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins and also water.
[0190] These formulations are prepared in a known manner, by mixing the active ingredients or combinations of the active ingredient with usual additives, for example, usual extenders and solvents or diluents, Petition 870260051039, dated 05 / 28 / 2026, page 97 / 314 94 / 149 colorants, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins and also water.
[0191] Useful dyes that may be present in seed treatment formulations are all dyes that are customary for such purposes. It is possible to use pigments that are moderately soluble in water, or dyes that are soluble in water. Examples include dyes known by the names Rhodamine B, CI Pigment Red 112, and CI Solvent Red 1. Useful wetting agents that may be present in seed treatment formulations are all substances that promote wetting and that are conventionally used for the formulation of active agrochemical ingredients. Preferably usable are alkylnaphthalenesulfonates, such as di-isopropyl or di-isobutylnaphthalenesulfonates. Useful dispersants and / or emulsifiers that may be present in seed treatment formulations are all non-ionic, anionic, and cationic dispersants conventionally used for the formulation of active agrochemical ingredients.Useful dispersants, preferably non-ionic or anionic, or mixtures of non-ionic or anionic dispersants, are preferred. Useful non-ionic dispersants include, in particular, ethylene oxide / propylene oxide block polymers, alkylphenol polyglycol ethers and tristrirylphenol polyglycol ether, 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 be used preferably. Preservatives that may be present in seed treatment formulations are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophen and alcohol. Petition 870260051039, dated 05 / 28 / 2026, page 98 / 314 95 / 149 benzyl 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 the usual binders usable in seed treatment products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tylose.
[0192] The compounds of formula (I) and compositions comprising them are suitable for protecting the seeds of any variety of plant that is used in agriculture, in greenhouses, in forests or in horticulture. More particularly, the seed is that of cereals (such as wheat, barley, rye, millet, triticale and oats), rapeseed, maize, cotton, soybean, rice, potatoes, sunflower, beans, coffee, peas, beet (for example, sugar beet and fodder beet), peanuts, vegetables (such as tomatoes, cucumbers, onions and lettuce), lawns and ornamental plants. Of particular significance is the treatment of seeds of wheat, soybean, rapeseed, maize and rice.
[0193] The compounds of formula (I) or compositions comprising them can be used to treat 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 the interaction with the substances formed by expression. Application
[0194] The compound of formula (I) may be applied as such, or for example, in the form of ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, soluble granules, Petition 870260051039, dated 05 / 28 / 2026, page 99 / 314 96 / 149 granules for dispersion, 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.
[0195] Application is carried out in a usual manner, for example, by irrigation, spraying, atomizing, dispersing, powdering, foaming, spreading and the like. It is also possible to implement the compound of formula (I) by the ultra-low volume method, by means of a drip irrigation system or watering application, to apply it in the furrow or inject it into the stem or trunk of the soil. It is also possible to apply the compound of formula (I) by means of a wound seal, ink or other wound dressing.
[0196] 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 used, the object of treatment (plant, plant part, fruit, seed or soil), the type of treatment (powdering, spraying, seed treatment), the purpose of the treatment (curative and protective), the type of microorganisms, the stage of development of the microorganisms, the sensitivity of the microorganisms, the stage of growth of the crop and the environmental conditions.
[0197] 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 10,000 g / ha, preferably from 10 to 1,000 g / ha, more preferably from 50 to 300 g / ha (in the case of irrigation or drip irrigation, it is possible to reduce the application rate, especially when 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 Petition 870260051039, dated 05 / 28 / 2026, pp. 100 / 314 97 / 149 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, even more preferably from 2.5 to 12.5 g per 100 kg of seeds. For soil treatment, the application rate can vary from 0.1 to 10,000 g / ha, preferably from 1 to 5,000 g / ha.
[0198] These application rates are merely examples and are not intended to limit the scope of the present invention. Material Protection
[0199] 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.
[0200] Furthermore, the compound and composition of the invention can be used as anti-fouling compositions, alone or in combination with other active ingredients.
[0201] Industrial materials in the present context are understood to mean inanimate materials that have been prepared for use in industry. For example, industrial materials that must be protected from microbial alteration or destruction may include adhesives, glues, paper, wallpaper and cardboard, textiles, carpets, leather, wood, fibers and fabrics, paints and plastic articles, refrigeration lubricants and other materials that may be infected or destroyed by microorganisms. Parts of production facilities and buildings, for example, 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 materials to be protected.The industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and cardboard, leather, wood, paints, cooling lubricants and heat transfer fluids, most preferably wood. Petition 870260051039, dated 05 / 28 / 2026, page 101 / 314 98 / 149
[0202] The compound and composition of the invention can prevent adverse effects such as rotting, decomposition, discoloration or mold formation.
[0203] In the case of wood treatment, the compound and composition of the invention can also be used against fungal diseases that can grow on or inside the wood.
[0204] 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, from fouling.
[0205] 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 of natural origin for which long-term protection is desired. Storage goods of plant origin, for example, plants or plant parts 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 wood, both unprocessed, such as timber for construction, poles and electricity barriers, and in the form of finished products such as furniture. Storage goods of animal origin are, for example, hides, leather and hair. The compound and composition of the invention can prevent adverse effects such as rotting, decay, discoloration or mold formation. Petition 870260051039, dated 05 / 28 / 2026, p. 102 / 314 99 / 149
[0206] 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.
[0207] The aspects of this teaching can be better understood in light of the following examples, which should not be interpreted as limiting the scope of this teaching in any way. EXAMPLES
[0208] In the following paragraphs, the detailed procedures for the synthesis of intermediates for compounds of the present invention are described. Synthesis of intermediates (VII) according to process P6 3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol Petition 870260051039, dated 05 / 28 / 2026, pp. 103 / 314 100 / 149
[0209] 3-(4-Bromophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (100 mg, 0.32 mmol), bis(pinacolate)diboron (123 mg, 0.48 mmol), [1,1-B / s(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (7.3 mg, 0.011 mmol) and potassium acetate (95 mg, 0.97 mmol) were dissolved in degassed dioxane (2 mL). The mixture was stirred at 80 °C for 3 h, then cooled to room temperature and diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent: heptane / ethyl acetate) to obtain the title compound (95 mg, 78% yield) as a light yellow honey. MS (ESI): 358 ([M+H]+) Synthesis of compounds of formula I 3-{4-[2-(Methylamino)pyrimidin-5-yl]phenyl}-5-(trifluoromethyl)-4,5-dihydro-1,2oxazol-5-ol (compound I-001)
[0210] N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (83 mg, 0.35 mmol) and [1,1-B / s(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (10 mg, 0.016 mmol) were added to a solution of cesium carbonate (115 mg, 0.35 Petition 870260051039, dated 05 / 28 / 2026, pp. 104 / 314 A solution of 101 / 149 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) were mixed. The mixture was stirred at 85 °C for 1 h, then cooled to room temperature. The reaction mixture was then concentrated and diluted with dichloromethane. The suspension was placed in a 2 g silica cartridge, eluted with dichloromethane, and evaporated. The residue was purified using preparative HPLC-MS (SunFire Waters, 30*150, 5 μm, eluent: acetonitrile / water (0.1% formic acid)) to obtain the title compound (43 mg, 39% yield). MS (ESI): 339 ([M+H]+) 3-[4-(pyrimidin-5-yl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-5-ol (compound I-008)
[0211] 3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)4,5-dihydro-1,2-oxazol-5-ol (80 mg, 0.22 mmol), 2-bromopyridine (0.021 mL, 0.22 mmol), [1,1-B / s(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (7.3 mg, 0.011 mmol) and cesium carbonate (73 mg, 0.22 mmol) were dissolved in degassed dioxane (1.5 mL) and degassed water (0.5 mL). The mixture was stirred at 80 °C for 1 h, then cooled to room temperature and diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by preparative HPLC-MS (eluent: acetonitrile / water (0.1% formic acid)) to obtain the title compound (28 mg, 40% yield) as a white solid. MS (ESI): 309 ([M+H]+) Petition 870260051039, dated 05 / 28 / 2026, page 105 / 314 102 / 149 5-[4-[5-Hydroxy-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]pyridino-2-carbonitrila (Compound I-029)
[0212] 3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)4,5-dihydro-1,2-oxazol-5-ol (300 mg, 0.84 mmol), 3-bromo-5-cyanopyridine (154 mg, 0.84 mmol), [1,1-B / s(di-ferc-butylphosphino)ferrocene]dichloropalladium(II) (27.7 mg, 0.042 mmol) and cesium carbonate (274 mg, 0.84 mmol) were dissolved in degassed dioxane (3 mL) and degassed water (1 mL). The mixture was stirred at 80 °C for 1 h, then cooled to room temperature and diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried on a phase-separating filter, and concentrated under reduced pressure. The residue was purified by flash chromatography (eluent: heptane / ethyl acetate) to obtain the title compound (180 mg, 63% yield) as a white solid. MS (ESI): 34 ([M+H]+) 3-[4-(6-Methoxypyridazin-3-yl)phenyl]-5-(tnfluoromethyl)-4H-1,2-oxazol-5-ol (Compost I-037) .
[0213] 3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)4,5-di-hydro-1,2-oxazol-5-ol (100 mg, 0.28 mmol), 3-chloro-6-methoxypyridazine (40 mg. Petition 870260051039, 05 / 28 / 2026, p. 106 / 3 103 / 1 0.28 mmol), [1,1-B / s(di-tert-butylphosphino)ferrocene]dichloropalladium(II) (9.1 mg, 0.014 mmol) and cesium carbonate (91 mg, 0.28 mmol) were dissolved in degassed dioxane (1.5 mL) and degassed water (0.5 mL). The mixture was stirred at 80 °C for 3 h, then cooled to room temperature and diluted with water and ethyl acetate. The layers were separated and the aqueous phase was extracted twice with ethyl acetate. The organic layers were combined, dried in a phase separator filter and concentrated under reduced pressure. The residue was purified by preparative HPLC-MS (eluent: acetonitrile / water (0.1% formic acid)) to obtain the title compound (20 mg, 19% yield) as a white solid. MS (ESI): 340 ([M+H]+) 3-(4-Pyrazin-2-ylphenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-5-ol (Compound 1-112)
[0214] 3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(trifluoromethyl)4,5-dihydro-1,2-oxazol-5-ol (144 mg, 0.40 mmol), 2-bromopyrazine (70 mg, 0.44 mmol), [1,1-B / s(di-ferc-butylphosphino)ferrocene]dichloropalladium(II) (13 mg, 0.02 mmol) and cesium carbonate (130 mg, 0.40 mmol) were dissolved in degassed dioxane (1.5 mL) and degassed water (0.5 mL). The mixture was stirred at 90 °C for 1 h, then cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in DCM, filtered through a silica gel cartridge, evaporated, and purified by preparative HPLC-MS (eluent: acetonitrile / water (0.1% formic acid)) to obtain the title compound (39 mg, 31% yield). MS (ESI): 310 ([M+H]+) Petition 870260051039, dated 05 / 28 / 2026, page 107 / 314 104 / 149
[0215] The compounds in Table 1 were prepared in analogy to the examples given above. Table 1: Compounds according to formula (I) Ex N° X R1 (F)m ( Het ) * <R2)n LogP 1.001 F H - 2-(metilamino)pirimidin-5-il 2,01[a] I.002 F H - 6-cianopiridin-2-il 2,80[a] I.003 F H 3-F 6-metoxipiridin-3-il 3,13[a] I.004 F H - 2-(4-fluorofenil)piridin-4-il 3,37[a] I.005 F H - 5-cloropiridin-3-il 2,92[a] I.006 F H 2-F 2-metoxipiridin-3-il 3,16[a] I.007 F H 5-fenilpiridin-3-il 3,01[a] I.008 F H piridin-2-il 2,05[a] I.009 F H 6-(trifluorometil)piridin-2-il 3,59[a] 1.010 F H 2-(dimetilamino)pirimidin-5-il 2,70[a] 1.011 F H 6-cloropiridin-2-il 3,31[a] 1.012 F H - 4-metilpirimidin-2-il 2,62[a] 1.013 Cl H - 6-metoxipiridin-3-il 3,07[a] I.014 F H - 3-cloropiridin-4-il 2,70[a] Petition 870260051039, dated 05 / 28 / 2026, p. 108 / 314 105 / 149 Ex N° X R1 (F)m ( Het) * <R2)n LogP 1.015 F H - 3-fenilpiridin~4-il 2,36[a] 1.016 F H 2-F 2-fluoropiridin-4-il 2,80[a] 1.017 Cl H - 2-fluoropiridin-4-il 2,83[a] 1.018 F H - 3-metilpiridin-4-il 1,37[a] 1.019 F H - 4-metoxipirimidin-5-il 2,31[a] 1.020 F H 6-metilsulfanilpiridin-3-il 3,13[a] 1.021 F H 2-metoxipirimidin-5-il 2,39[a] 1.022 F H 2-metilsulfanilpirimidin-5-il 2,95[a] 1.023 F H 3-F 6-fluoropiridin-3-il 2,95[a] 1.024 F H 4-(trifluorometil)pirimidin-5-il 2,75[a] I.025 F H 6-metilpiridin-2-il 1,84[a] 1.026 F H - 2-metilsulfanilpiridin-3-il 3,22[a] I.027 F H - 4-isopropilpirim idin-5-il 2,67[a] I.028 F H - 5-metoxipirimidin-2-il 2,64[a] I.029 F H - 6-cianopiridin-3-il 2,62[a] I.030 F H - 2-metilpiridin-4-il 1,30[a] 1.031 F H - 5-(4-fluorofenil)piridin-3-il 3,13[a] 1.032 F H 2-(trifluorometil)pirimidin-5-il 3,13[a] I.033 F H 6-(benzilamino)piridin-3-il 2,01[a] 1.034 F H 3-F 2-metoxipiridin-3-il 3,04[a] I.035 Cl H 2-metoxipiridin-3-il 3,10[a] 1.036 F H 6-metoxipiridin-2-il 3,40[a] I.037 FH 6-methoxypyridazine-3-yl 2.36[a] I.038 FH - 2-chloropyridine-4-yl 2.92[a] I.039 FH 2-F 6-methoxypyridine-3-yl 3.10[a]. Petition 870260051039, of 28 / 05 / 2026, p. 109 / 314 106 / 149 Ex N° X R1 (F)m ( Het ) * <R2)n LogP 1.040 F H 3-F 2-fluoropiridin-4-il 2,86[a] 1.041 F H - 3-(4-fluorofenil)piridin-4-il 3,06[a] 1.042 F H - 5-metilpiridin-3-il 1,56[a] 1.043 F H - 6-(4-fluorofenil)piridin-2-il 4,24[a] 1.044 F H - 4-cianopirimidin-5-il 2,39[a] 1.045 F H 2-cianopirimidin-5-il 2,60[a] 1.046 F H 2-metilpirimidin-5-il 2,02[a] 1.047 F H 6-fenilpiridin-2-il 4,15[a] 1.048 F H 2-fenilpiridin-4-il 2,95[a] 1.049 F H 2,6-difluoropiridin-4-il 3,22[a] I.050 F H 3-metilpirazin-2-il 2,13[a] 1.051 F H - 4-am inopiridin-2-il 1,10[a] 1.052 F H - 4-fluoropiridin-2-il 2,71[a] I.053 F H - 5-fluoropiridin-3-il 2,55[a] 1.054 F H - 5-fluoropiridin-2-il 2,85[a] I.055 F H - 6-fluoropiridin-2-il 2,99[a] 1.056 F H - 3-(trifluorometil)piridin-4-il 2,83[a] I.057 F H 2-etinilpiridin-4-il 2,48[a] I.058 F H 5-etinilpiridin-3-il 2,66[a] I.059 F H 6-(trifluorometil)piridazin-3-il 2,91[a] 1.060 F H 2-cianopiridin-4-il 2,62[a] 1.061 F H 2-cianopiridin-3-il 2,44[a] 1.062 F H 4-cianopiridin-3-il 2,32[a] 1.063 FH - 4-cyanopyridine-2-yl 2,73[a] I.064 FH - 3-methoxypyridine-2-yl 2,03[a]. Petition 870260051039, dated 5 / 28 / 2026, p. 110 / 314 107 / 149 Ex N° X R1 (F)m ( Het ) * <R2)n LogP 1.065 F H - 2-(hidroximetil)piridin-4-il 1,19[a] 1.066 F H - 3-cianopiridin-2-il 2,38[a] 1.067 F H - 2-fluoropirim idin-5-il 2,44[a] 1.068 F H - 2-formilpiridin-4-il 2,39[a] 1.069 F H - 2-formilpiridin-3-il 2,12[a] 1.070 F H 4-formilpiridin-2-il 2,53[a] 1.071 F H 2-cloro-6-fluoropiridin-4-il 3,50[a] 1.072 F H 6-(trifluorometil)piridin-3-il 3,29[a] 1.073 F H 2,5-dicloropiridin-3-il 3,50[a] 1.074 F H 2-am inopiridin-3-il 1,18[a] 1.075 F H 2-(2-fluorofenóxi)piridin-3-il 3,64[a] 1.076 F H - 4-(trifluorometil)pirimidin-2-il 3,50[a] 1.077 F H - 2-hidroxipirimidin-5-il 1,41[a] 1.078 F H - 2-terc-butoxipirim idin-5-il 3,50[a] 1.079 F H - 2-cloropiridin-3-il 2,69[a] 1.080 F H - 5-cloropiridin-2-il 3,30[a] 1.081 F H - 6-cloropiridin-3-il 2,97[a] 1.082 F H 4-cloropiridin-2-il 3,15[a] 1.083 F H 2-cloropirimidin-5-il 2,61[a] 1.084 F H 2-(dimetilam ino)piridin-4-il 1,46[a] I.085 F H 2-etoxipiridin-3-il 3,34[a] 1.086 F H 2-etoxipiridin-4-il 3,22[a] I.087 FH 4-fluoro-2-methoxypyridine-3-yl 3,07[a] I.088 FH - 3-cyano-4-(trifluoromethyl)pyridine-2-yl 3,10[a] I.089 FH - 2-(difluoromethyl].yl.58pyridine-3-yl. Petition 870260051039, dated 5 / 28 / 2026, p. 111 / 314 108 / 149 Ex N° X R1 (F)m ( Het ) * <R2)n LogP 1.090 F H - 2-terc-butilpiridin~4-il 2,03[a] 1.091 F H - 2-propoxipiridin~4-il 3,67[a] 1.092 F H - 2-(difluorometóxi)piridin-3-il 3,24[a] 1.093 F H - 2,4-difluoropiridin-3-il 2,73[a] 1.094 F H - 2-(trifluorometil)piridin-3-il 2,94[a] I.095 F H 4-(trifluorometil)piridin-2-il 3,46[a] 1.096 F H 5-(dimetoximetil)piridin-3-il 2,21[a] I.097 F H 2-[cloro(difluoro)metil]piridin-4-il 3,37[a] I.098 F H 4-(2-fluoropiridin-4-il)pirimidin-2-il 3,21[a] 1.099 F H 6-metóxi-4-(trifluorometil)piridin-3il 3,75[a] 1.100 F H 2-metoxipiridin-4-il 2,85[a] 1.101 F H - 3-(trifluorometil)piridin-2-il 2,91[a] 1.102 F H - 2-am inopiridin-4-il 1,22[a] 1.103 F H - 2-metilpiridin-3-il 1,22[a] 1.104 F H - 2-benziloxipirimidin-5-il 3,50[a] 1.105 F H - 3-fluoropiridin-2-il 2,68[a] 1.106 F H - 4-metilpiridazin-3-il 1,84[a] 1.107 F H 3-cianopirazin-2-il 2,42[a] 1.108 F H 4-cianopirimidin-2-il 2,79[a] 1.109 F H 4-metoxipirimidin-2-il 2,91[a] 1.110 F H 3-metoxipirazin-2-il 2,76[a] 1.111 FH 4-(cyanomethyl)pyridin-2-yl 2.51[a] 1.112 FH pyrazin-2-yl 2.16[a] I.113 FH - pyrimidin-2-yl 2.31[a]. Petition 870260051039, dated 05 / 28 / 2026, page 112 / 314 109 / 149 Ex N° X R1 (F)m ( Het ) * <R2)n LogP 1.114 F H - 6-metilpiridazin-3-il 1,89[a] I.115 F H - 2,5-difluoropiridin-4-il 3,01[a]
[0216] The LogP values were measured in accordance with EEC Directive 79 / 831 Annex V.A8 by HPLC (High-Performance Liquid Chromatography) on reversed-phase columns using the following methods: [a]The LogP value is determined by LC-UV measurement, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). [b]The LogP value is determined by LC-UV measurement, in a neutral range, with a 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). [c]The LogP value is determined by LC-UV measurement, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).
[0217] If more than one LogP value is available within the same method, all values are provided and separated by “+”.
[0218] 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). Maximum lambda values were determined using UV spectra from 200 nm to 400 nm and peak values from chromatographic signals. NMR peak lists
[0219] The 1H NMR data from selected examples are written in the form of lists of 1H NMR peaks. For each signal peak, the δ value is listed. Petition 870260051039, dated 05 / 28 / 2026, pp. 113 / 314 110 / 149 in ppm and the signal intensity in square brackets. Between the δ value, the signal intensity pairs are delimited by periods and commas.
[0220] The list of peaks in an example therefore has the form: δι (intensityi); δ2 (intensity2);........; δι (intensityi);......; δn (intensityn)
[0221] The intensity of sharp signals correlates to 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.
[0222] To calibrate the chemical shift for 1H spectra, tetramethylsilane and / or the chemical shift of the solvent used is employed, especially in the case of spectra measured in DMSO. Therefore, in the NMR peak lists, the tetramethylsilane peak may occur, but not necessarily.
[0223] 1H NMR peak lists are similar to classic 1H NMR printouts and therefore usually contain all the peaks that are listed in the classic NMR interpretation.
[0224] Additionally, they may show 1H NMR impression signs of solvents, stereoisomers of the target compounds, which are also objects of the invention and / or impurity peaks.
[0225] To show signals of compounds 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 1H NMR peak lists and usually have on average a high intensity.
[0226] The stereoisomer peaks of the target compounds and / or impurity peaks usually have on average a lower intensity than the peaks of the target compounds (for example, with a purity >90%). Petition 870260051039, dated 05 / 28 / 2026, pp. 114 / 314 111 / 149
[0227] Such stereoisomers and / or impurities may be typical for the specific preparation process. Therefore, their peaks can help to recognize the reproduction of the preparation process through “byproduct fingerprints”.
[0228] 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 would be similar to the relevant peak in the classical 1H NMR interpretation.
[0229] Further details on the description of NMR data with peak lists can be found in the Research Disclosure Database publication “Citation of NMR Peaklist Data in Patent Applications” Number 564025. 1.001: 1H NMR (400.1 MHz, d6-DMSO): δ= 8.7111 (3.0); 8.6247 (2.3); 7.7630 (16.0); 7.3501 (0.9); 7.3382 (0.9); 3.9724 (1.4); 3.9263 (1.7); 3.5977 (1.1); 3.5516 (0.9); 3.3053 (42.1); 2.8904 (0.8); 2.8645 (5.9); 2.8526 (5.8); 2.7314 (0.6); 2.5049 (11.2); 2.5006 (14.7); 2.4962 (10.8); -0.0002 (9.1) I. 002: 1H NMR (400.1 MHz, d6-DMSO): δ= 8.7056 (4.2); 8.4228 (4.1); 8.4023 (4.9); 8.2505 (7.9); 8.2308 (8.8); 8.2102 (2.5); 8.1909 (4.6); 8.1712 (2.5); 8.0594 (5.2); 8.0405 (4.0); 7.9605 (4.0); 7.9084 (8.6); 7.8886 (7.8); 4.0366 (3.7); 3.9899 (4.6); 3.6470 (3.9); 3.5998 (3.1); 3.3187 (192.0); 2.8995 (16.0); 2.7404 (15.5); 2.5104 (29.2); 1.1979 (0.5); 1.1640 (0.5) Petition 870260051039, dated 05 / 28 / 2026, pp. 115 / 314 112 / 149 1.003: 1H NMR (400.1 MHz, CDCI3): δ= 8.3746(1.9); 8.0111 (0.5); 7.8163(0.8); 7.8113(1.2); 7.8064 (0.8); 7.7945 (0.9); 7.7898 (1.2); 7.7846 (0.8); 7.5233 (1.6); 7.4974 (4.9); 7.4865 (3.0); 7.2587 (34.4); 6.8588 (2.3); 6.8373 (2.5); 3.9965 (16.0); 3.9794 (2.1); 3.7474 (1.6); 3.7029 (2.4); 3.6047 (0.6); 3.5467 (1.6); 3.5021 (1.0); 2.9552 (3.3); 2.8808 (3.1); 1.5397 (15.3); 1.2843 (0.5); 1.2570 (2.7); 0.8812 (0.5); -0.0002 (42.9) 1.004: RMN de1H (300.2 MHz, d6-DMSO): δ = 8.7763 (1.6); 8.7594 (1.9); 8.7436 (2.6); 8.3447 (1.5); 8.3268 (3.6); 8.3160 (2.2); 8.2967 (1.6); 8.1224 (2.3); 8.0943 (3.1); 7.9225 (3.0); 7.8947 (2.5); 7.7772 (1.2); 7.7602 (1.3); 7.4023 (1.4); 7.3729 (2.7); 7.3434 (1.4); 4.0765 (1.1); 4.0143 (1.5); 3.6869 (1.1); 3.6248 (0.8); 3.3524 (16.0); 2.5231 (10.8); 2.0103 (0.4); 0.0201 (5.3) 1,005: RMN de1H (300.2 MHz, d6-DMSO): δ= 8.9776(1.7); 8.9711 (1.7); 8.7289(1.4); 8.6936(1.6); 8.6860 (1.6); 8.3818 (1.1); 8.3747 (1.9); 8.3675 (1.1); 7.9812 (1.6); 7.9528 (3.0); 7.8851 (2.9); 7.8566 (1.6); 4.0531 (0.9); 3.9910 (1.2); 3.6618 (0.8); 3.6010 (0.6); 3.3490 (16.0); 2.5339 (3.8); 2.5281 (7.8); 2.5221 (10.5); 2.5161 (7.6); 2.5102 (3.6); 2.0095 (0.8); 1.1944 (0.4); 0.0306 (0.5); 0.0199 (11.0); 0.0088 (0.4) I.006: de1H NMR (400.1 MHz, CDCl3): δ= 8.2227 (1.3); 8.2181 (1.4); 8.2103 (1.4); 8.2057 (1.3); 8.0055 (0.5); 7.9625 (1.1); 7.9430 (1.8); 7.9221 (1.0); 7.6555 (1.4); 7.6508 (1.4); 7.6371 (1.5); 7.6324 (1.5); 7.4430 (1.2); 7.4393 (1.5); 7.4279 (1.5); 7.4243 (1.5); 7.4115 (1.4); 7.4074 (3.4); 7.2590 (11.4); 7.0196 (1.4); 7.0071 (1.4); 7.0012 (1.4); 6.9887 (1.3); 3.9957 (16.0); 3.8580 (0.8); 3.8525 (0.8); 3.8115 (1.4); 3.8062 (1.3); 3.7207 (0.6); 3.6636 (1.0); 3.6604 (1.0); 3.6173 (0.6); 3.6138 (0.6); 2.9557 (3.9); 2.8787 (3.5); 1.5640 (3.8); 1.2569 (1.6); 0.0076 (0.7); 0.0002 (13.4) Petition 870260051039, dated 05 / 28 / 2026, page 116 / 314 113 / 149 1.007: 1Η NMR (300.2 MHz, d6-DMSO): δ= 8.9904 (0.5); 8.9832 (0.4); 8.9509 (0.5); 8.9439 (0.5); 8.7220 (0.4); 8.4108 (0.5); 8.0501 (0.5); 8.0217 (0.7); 7.9125 (0.4); 7.9075 (0.7); 7.9011 (0.8); 7.8844 (0.6); 7.8730 (0.6); 7.5671 (0.5); 7.5418 (0.4); 3.3477 (16.0); 2.5341 (3.8); 2.5282 (7.8); 2.5221 (10.6); 2.5161 (7.7); 2.5102 (3.8); 0.0312 (0.5); 0.0203 (12.5); 0.0094 (0.6) 1.008: 1H NMR (300.2 MHz, d6-DMSO): δ= 8.7347 (0.5); 8.7318 (0.5); 8.7188 (0.6); 8.7158 (0.6); 8.7070 (2.0); 8.2517 (1.4); 8.2231 (1.6); 8.0985 (0.6); 8.0717 (0.8); 7.9733 (0.4); 7.9671 (0.4); 7.9480 (0.6); 7.9420 (0.5); 7.9217 (0.3); 7.8810 (1.6); 7.8524 (1.4); 7.4496 (0.4); 7.4463 (0.4); 7.4337 (0.4); 7.4303 (0.4); 7.4248 (0.4); 7.4216 (0.4); 7.4088 (0.4); 7.4055 (0.4); 4.0508 (0.6); 3.9889 (0.8); 3.6547 (0.5); 3.5934 (0.4); 3.3520 (16.0); 2.5342 (3.1); 2.5283 (6.2); 2.5222 (8.5); 2.5162 (6.2); 2.5102 (3.0); 0.0201 (7.0) 1.009: RMN de1H (400.1 MHz, d6-DMSO): δ = 8.7049 (9.8); 8.4066 (5.7); 8.3863 (6.9); 8.2725 (11.5); 8.2524 (16.0); 8.2327 (6.4); 8.2131 (3.1); 7.9609 (4.0); 7.9150 (14.0); 7.8965 (11.4); 4.0344 (5.3); 3.9883 (6.6); 3.6482 (5.5); 3.6021 (4.4); 3.3182 (354.5); 2.8999 (16.0); 2.7408 (15.4); 2.6765 (0.4); 2.6528 (0.5); 2.5106 (49.4); 2.3336 (0.3) 1.010: RMN de1H (400.1 MHz, d6-DMSO): δ= 8.7783 (5.6); 8.6300 (1.3); 7.7727 (8.3); 3.9715 (0.8); 3.9253 (1.0); 3.5998 (0.6); 3.5530 (0.5); 3.3031 (18.0); 3.1832 (16.0); 2.5049 (4.2); 2.5004 (5.4); 2.4960 (3.9); 0.0002 (5.2) I.011: RMN de1H (400.1 MHz, d6-DMSO): δ= 8.6824 (13.1); 8.1960 (14.1); 8.1749 (16.0); 8.1018 (7.1); 8.0825 (10.2); 8.0089 (6.4); 7.9894 (10.7); 7.9699 (5.0); 7.9527 (1.2); 7.8746 (16.0); 7.8535 (13.9); 7.5371 (9.8); 7.5176 (8.9); 4.0185 (6.5); 3.9722 (8.1); 3.6290 (5.2); 3.5823 (4.1); 3.3044 (206.3); 2.8906 (7.4); 2.7316 (6.6); 2.5050 (39.2); 2.5007 (51.0); 2.4964 (37.0); 1.2348 (0.6); 0.0002 (27.3) Petition 870260051039, dated 05 / 28 / 2026, pp. 117 / 314 114 / 149 1.012: 1H NMR (400.1 MHz, d6-DMSO): δ= 8.7953 (7.2); 8.7832 (7.3); 8.6974 (3.2); 8.4970 (11.9); 8.4774 (12.7); 7.9612 (3.9); 7.8938 (12.6); 7.8742 (11.8); 7.3864 (7.3); 7.3741 (7.0); 4.0274 (5.4); 3.9812 (6.7); 3.6361 (5.7); 3.5901 (4.6); 3.3199 (180.1); 2.8994 (16.0); 2.7404 (15.5); 2.5743 (40.2); 2.5474 (1.0); 2.5107 (29.8); 1.1974 (1.1); 1.1635 (1.1) 1.013: 1H NMR (400.1 MHz, CDCI3): δ= 8.4257 (1.9); 8.4201 (1.9); 7.8281 (1.3); 7.8217 (1.3); 7.8066 (1.4); 7.8002 (1.4); 7.7523 (2.7); 7.7313 (3.8); 7.6114 (3.8); 7.5903 (2.8); 7.2587 (26.0); 6.8550 (1.9); 6.8337 (1.9); 3.9943 (16.0); 3.9794 (2.6); 3.8289 (1.4); 3.7843 (2.0); 3.6111 (0.5); 3.5878 (1.4); 3.5433 (0.9); 2.9539 (0.6); 2.8800 (0.6); 1.5409 (6.8); 1.2846 (0.6); 1.2567 (3.2); 0.8809 (0.6); 0.8635 (0.4); 0.8532 (0.5); 0.8366 (0.4); 0.0079 (1.2); -0.0002 (31.6) 1.014: de1H NMR (300.2 MHz, d6-DMSO): δ= 8.7928 (3.1); 8.7455 (1.3); 8.6513 (2.0); 8.6349 (2.0); 7.9070 (2.3); 7.8791 (2.9); 7.6858 (3.0); 7.6578 (2.3); 7.5659 (1.8); 7.5495 (1.7); 4.0609 (1.1); 3.9989 (1.3); 3.6649 (0.8); 3.6026 (0.6); 3.3509 (16.0); 2.5280 (7.6); 2.5220 (10.3); 2.5161 (7.5); 1.1780 (1.6); 1.0877 (2.2); 0.0197 (7.5) I.015: de1H NMR (300.2 MHz, d6-DMSO): δ= 8.6973 (1.1); 8.6804 (1.4); 8.6392 (1.8); 7.6830 (1.4); 7.6551 (1.7); 7.5203 (1.0); 7.5036 (1.0); 7.3567 (0.9); 7.3509 (0.9); 7.3395 (1.8); 7.3335 (2.0); 7.3172 (1.8); 7.2893 (1.5); 7.2289 (1.0); 7.2184 (0.8); 7.2037 (0.9); 7.1970 (0.6); 3.9740 (0.6); 3.9119 (0.8); 3.5721 (0.5); 3.5104 (0.4); 3.3488 (16.0); 2.5342 (5.1); 2.5283 (11.0); 2.5223 (15.3); 2.5163 (11.1); 2.5107 (5.3); 0.0312 (0.4); 0.0203 (10.4) Petition 870260051039, dated 05 / 28 / 2026, pp. 118 / 314 115 / 149 1.016: 1H NMR (400.1 MHz, CDCI3): δ= 8.3382 (5.6); 8.3250 (5.8); 8.0822 (3.3); 8.0628 (5.8); 8.0432 (4.0); 8.0250 (0.6); 8.0124 (0.9); 7.8151 (0.6); 7.7965 (0.8); 7.7142 (0.4); 7.6981 (0.7); 7.6789 (0.5); 7.5427 (0.7); 7.5356 (1.0); 7.5234 (1.2); 7.5140 (4.8); 7.5098 (4.7); 7.4934 (3.9); 7.4893 (4.1); 7.4461 (4.3); 7.4420 (4.2); 7.4167 (4.6); 7.4120 (4.4); 7.4047 (4.7); 7.4007 (3.3); 7.3957 (3.6); 7.3918 (4.9); 7.3664 (1.0); 7.3482 (0.5); 7.3374 (0.4); 7.3187 (0.5); 7.2923 (0.7); 7.2588 (103.2); 7.1369 (7.2); 6.9950 (0.8); 4.0862 (0.5); 3.8661 (2.6); 3.8602 (2.5); 3.8380 (1.9); 3.8198 (4.1); 3.8139 (3.9); 3.6718 (3.3); 3.6259 (2.2); 3.6214 (2.3); 3.5704 (1.0); 3.5224 (0.5); 2.9560 (6.6); 2.8816 (5.9); 2.8041 (0.4); 2.7855 (0.3); 2.6028 (0.4); 1.6809 (0.3); 1.6551 (0.4); 1.5421 (28.2); 1.4030 (0.6); 1.3700 (1.0); 1.3321 (1.1); 1.2850 (3.0); 1.2569 (16.0); 1.0907 (0.6); 0.9963 (0.4); 0.9334 (0.5); 0.8970 (1.6); 0.8807 (3.2); 0.8631 (2.3); 0.8535 (2.3); 0.8364 (2.0); 0.8153 (1.1); 0.7750 (0.4); 0.1461 (0.6); 0.0077 (6.3); -0.0002 (122.6); -0.1494 (0.6) I.017: de1H NMR (400.1 MHz, CDCl3): δ= 8.3166 (7.1); 8.3035 (7.3); 7.8174 (10.3); 7.7962 (15.8); 7.7163 (16.0); 7.6951 (10.1); 7.5174 (0.5); 7.4284 (3.3); 7.4245 (5.2); 7.4203 (3.5); 7.4155 (3.5); 7.4114 (5.0); 7.4073 (3.0); 7.2589 (77.5); 7.1518 (9.2); 6.9949 (0.4); 4.0867 (0.4); 3.8368 (5.7); 3.7921 (8.0); 3.6637 (3.7); 3.5967 (5.5); 3.5519 (3.8); 2.9549 (1.7); 2.8800 (1.6); 1.6064 (0.5); 1.5436 (45.4); 1.4045 (0.4); 1.3917 (0.3); 1.3699 (0.6); 1.2853 (2.1); 1.2567 (11.5); 1.0956 (0.4); 1.0724 (0.4); 0.9356 (0.4); 0.8951 (1.1); 0.8808 (2.3); 0.8624 (1.5); 0.8531 (1.6); 0.8380 (1.4); 0.8137 (0.8); 0.1462 (0.5); 0.0077 (4.6); -0.0002 (91.8); -0.0082 (5.0); 0.1496 (0.5) Petition 870260051039, dated 05 / 28 / 2026, p. 119 / 314 116 / 149 1.018: 1H NMR (300.2 MHz, CDCI3): δ= 8.5475 (4.1); 8.5216 (2.4); 8.5049 (2.4); 7.8168 (4.6); 7.7895 (5.4); 7.4488 (5.3); 7.4215 (4.6); 7.2996 (15.5); 7.2120 (2.7); 7.1954 (2.6); 3.8318 (1.7); 3.7726 (3.1); 3.6226 (2.2); 3.5627 (1.3); 2.3172 (16.0); 2.0850 (0.7); 1.6835 (0.8); 1.6713 (0.8); 1.6420 (0.8); 1.4981 (0.4); 1.4626 (0.4); 1.4294 (0.4); 1.3093 (2.9); 1.2911 (4.9); 1.2809 (5.8); 1.2462 (0.7); 1.2138 (0.4); 0.9163 (0.7); 0.8897 (1.0); 0.8657 (1.0); 0.1075 (9.3); 0.0834 (0.5); 0.0482 (0.6); 0.0372 (11.3) 1.019: RMN de1H (300.2 MHz, d6-DMSO): δ= 8.8476 (1.1); 8.7190 (0.9); 8.6802 (1.2); 7.8532 (0.6); 7.8247 (1.2); 7.7708 (1.2); 7.7423 (0.6); 4.0373 (0.4); 4.0334 (0.4); 4.0122 (4.4); 3.9713 (0.5); 3.3483 (16.0); 2.5346 (1.5); 2.5287 (3.0); 2.5226 (4.1); 2.5165 (3.0); 2.5106 (1.4); 2.0099 (0.9); 1.1952 (0.5); 1.0888 (0.4); 0.0206 (4.1) 1,020: RMN de1H (400.2 MHz, d6-DMSO): δ = 8.8484 (1.7); 8.8471 (1.8); 8.8426 (1.9); 8.8411 (1.8); 8.8067 (0.3); 8.8024 (0.3); 8.6804 (1.9); 8.0475 (1.2); 8.0414 (1.2); 8.0264 (1.3); 8.0203 (1.3); 7.8642 (1.2); 7.8424 (5.2); 7.8286 (5.0); 7.8068 (1.2); 7.4275 (1.8); 7.4261 (1.8); 7.4166 (0.4); 7.4148 (0.4); 7.4065 (1.7); 7.4050 (1.7); 7.3956 (0.4); 7.3939 (0.3); 4.0001 (1.3); 3.9539 (1.7); 3.6217 (1.0); 3.5752 (0.8); 3.3306 (10.5); 2.8918 (1.2); 2.7334 (1.1); 2.7323 (1.1); 2.5646 (16.0); 2.5538 (3.2); 2.5213 (0.5); 2.5126 (7.5); 2.5082 (15.6); 2.5037 (20.6); 2.4991 (14.9); 2.4947 (7.3); -0.0002 (1.8) I.021: RMN de1H (300.2 MHz, d6-DMSO): δ= 9.0482 (10.8); 8.7240 (0.8); 7.9204 (1.5); 7.8917 (4.9); 7.8651 (4.8); 7.8365 (1.5); 4.0613 (0.4); 4.0342 (1.3); 4.0019 (16.0); 3.9721 (1.7); 3.6531 (1.1); 3.5901 (0.8); 3.3466 (15.6); 2.5345 (5.1); 2.5286 (10.9); 2.5226 (15.1); 2.5166 (11.0); 2.5107 (5.1); 2.0099 (1.6); 1.2188 (0.4); 1.1951 (0.8); 1.1714 (0.4); 1.0888 (0.6); 0.0314 (0.4); 0.0206 (11.6); 0.0098 (0.4) Petition 870260051039, dated 05 / 28 / 2026, pp. 120 / 314 117 / 149 1.022: 1Η NMR (300.2 MHz, d6-DMSO): δ= 9.0850 (2.1); 8.7182 (0.8); 7.9546 (0.4); 7.9259 (0.8); 7.8802 (0.8); 7.8516 (0.3); 4.0612 (0.6); 4.0376 (0.7); 3.3463 (16.0); 2.5982 (3.1); 2.5343 (3.1); 2.5284 (6.3); 2.5224 (8.5); 2.5163 (6.2); 2.5104 (3.0); 2.0099 (2.7); 1.2188 (0.7); 1.1951 (1.5); 1.1714 (0.7); 0.0207 (6.8) 1.023: 1H NMR (300.2 MHz, d6-DMSO): δ= 8.8145 (2.4); 8.5176 (3.0); 8.3106 (0.7); 8.3054 (0.9); 8.2971 (0.7); 8.2765 (1.7); 8.2559 (0.8); 8.2507 (1.0); 8.2475 (0.9); 8.2426 (0.7); 7.8101 (1.4); 7.7838 (3.6); 7.7644 (2.6); 7.7570 (4.5); 7.7357 (3.6); 7.7308 (4.8); 7.7259 (3.8); 7.7206 (2.5); 7.7087 (2.1); 7.7035 (1.5); 7.4019 (2.2); 7.3923 (2.3); 7.3734 (2.2); 7.3638 (2.2); 4.0506 (2.7); 3.9882 (3.6); 3.6683 (2.2); 3.6050 (1.6); 3.3484 (16.0); 2.5343 (6.1); 2.5283 (13.2); 2.5222 (18.2); 2.5161 (13.0); 2.5102 (6.0); 2.0091 (0.4); 0.0302 (0.6); 0.0286 (0.3); 0.0270 (0.4); 0.0194 (18.4); 0.0117 (0.5); 0.0101 (0.5); 0.0085 (0.7) 1,024: RMN de1H (300.2 MHz, d6-DMSO): δ= 9.5174 (1.2); 9.1234 (1.6); 8.7459 (0.3); 7.9117 (1.2); 7.8834 (1.4); 7.6207 (1.2); 7.5933 (1.0); 4.0683 (0.5); 4.0064 (0.6); 3.6689 (0.4); 3.3484 (16.0); 2.5340 (1.9); 2.5281 (3.8); 2.5221 (5.1); 2.5160 (3.6); 2.5101 (1.7); 0.0199 (4.9) I.025: RMN de1H (400.1 MHz, d6-DMSO): δ= 8.6721 (2.0); 8.2110 (9.6); 8.1915 (10.5); 7.9606 (1.6); 7.8456 (16.0); 7.8267 (13.2); 7.8062 (5.3); 7.7870 (2.0); 7.2825 (5.6); 7.2644 (5.1); 4.0134 (4.4); 3.9671 (5.5); 3.6294 (4.7); 3.5828 (3.7); 3.4529 (0.5); 3.3228 (251.2); 2.8990 (6.5); 2.7402 (6.3); 2.5671 (33.0); 2.5105 (30.8) Petition 870260051039, dated 05 / 28 / 2026, pp. 121 / 314 118 / 149 1.026: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.6932 (1.4); 8.5284 (1.6); 8.5241 (1.8); 8.5163 (1.7); 8.5120 (1.7); 7.9529 (1.7); 7.8315 (3.4); 7.8106 (4.1); 7.5928 (1.5); 7.5885 (1.6); 7.5739 (2.2); 7.5683 (4.8); 7.5470 (3.6); 7.2618 (1.6); 7.2497 (1.6); 7.2431 (1.5); 7.2309 (1.5); 4.0165 (1.6); 3.9702 (1.9); 3.6247 (1.2); 3.5784 (1.0); 3.3287 (10.9); 2.8913 (11.8); 2.7319 (10.2); 2.5252 (0.4); 2.5117 (9.7); 2.5073 (20.0); 2.5028 (26.5); 2.4982 (19.0); 2.4938 (9.2); 2.4574 (16.0); 1.2397 (0.4); -0.0002 (2.2) 1.027: 1H NMR (400.2 MHz, d6-DMSO): δ= 9.1735 (6.5); 8.6963 (5.3); 8.6092 (6.6); 7.9537 (3.0); 7.8730 (5.1); 7.8528 (5.8); 7.5545 (5.8); 7.5343 (5.1); 4.0259 (2.4); 3.9795 (3.0); 3.6398 (2.3); 3.5932 (1.8); 3.3289 (18.6); 3.1467 (0.6); 3.1299 (1.4); 3.1134 (1.9); 3.0967 (1.4); 3.0797 (0.6); 2.8924 (15.3); 2.7329 (14.7); 2.6722 (0.3); 2.5579 (0.3); 2.5037 (50.0); 1.2404 (0.8); 1.1739 (16.0); 1.1575 (15.6); -0.0002 (2.5) 1.028: de1H NMR (400.1 MHz, d6-DMSO): δ= 8.6940 (11.0); 8.4096 (4.6); 8.3902 (4.9); 7.9609 (2.7); 7.8703 (4.9); 7.8509 (4.5); 4.0126 (2.4); 3.9872 (16.0); 3.9664 (2.7); 3.6270 (2.2); 3.5807 (1.8); 3.3195 (62.4); 2.8995 (11.2); 2.7404 (10.8); 2.5106 (12.0) I.029: de1H NMR (400.2 MHz, d6-DMSO): δ= 9.1870 (4.4); 9.1822 (4.5); 8.7207 (6.0); 8.4556 (2.3); 8.4500 (2.3); 8.4353 (2.7); 8.4295 (2.7); 8.1785 (4.2); 8.1581 (3.6); 7.9984 (5.3); 7.9773 (8.2); 7.9539 (2.5); 7.8992 (8.1); 7.8781 (5.4); 4.0270 (3.0); 3.9805 (3.8); 3.6446 (2.4); 3.5982 (2.0); 3.3325 (38.2); 2.8927 (16.0); 2.7335 (14.4); 2.6732 (0.3); 2.5263 (1.2); 2.5129 (21.9); 2.5087 (43.1); 2.5043 (55.6); 2.4998 (40.6); 2.4956 (20.5); 1.2383 (0.7); -0.0002 (3.7) Petition 870260051039, dated 05 / 28 / 2026, page 122 / 314 119 / 149 1.030: 1Η NMR (300.2 MHz, d6-DMSO): δ= 8.7340 (1.4); 8.5586 (1.4); 8.5413 (1.4); 7.9596 (1.5); 7.9312 (3.5); 7.8872 (3.4); 7.8588 (1.5); 7.6825 (1.7); 7.6008 (0.9); 7.5963 (0.8); 7.5836 (0.9); 7.5786 (0.8); 4.0532 (1.0); 3.9913 (1.4); 3.6605 (0.9); 3.5966 (0.6); 3.3592 (16.0); 3.1952 (0.5); 3.1785 (0.5); 2.5665 (8.7); 2.5334 (2.1); 2.5278 (4.1); 2.5218 (5.4); 2.5159 (3.9); 0.0184 (4.6) 1.031: 1H NMR (300.2 MHz, d6-DMSO): δ= 8.9862 (0.6); 8.9790 (0.6); 8.9397 (0.6); 8.9327 (0.7); 8.7247 (0.6); 8.4170 (0.4); 8.4097 (0.7); 8.4026 (0.4); 8.0500 (0.7); 8.0217 (1.0); 7.9853 (0.5); 7.9674 (0.5); 7.9558 (0.6); 7.9378 (0.5); 7.8995 (1.0); 7.8714 (0.7); 7.4278 (0.5); 7.3983 (1.0); 7.3687 (0.5); 4.0631 (0.4); 4.0016 (0.4); 3.3497 (16.0); 2.5345 (3.5); 2.5286 (7.6); 2.5226 (10.6); 2.5165 (7.8); 2.5108 (3.7); 0.0205 (6.2) 1.032: de1H NMR (300.2 MHz, d6-DMSO): δ= 9.5045 (3.8); 8.7648 (0.4); 8.0920 (1.2); 8.0636 (1.8); 7.9564 (1.8); 7.9280 (1.2); 4.0668 (0.6); 4.0049 (0.8); 3.6844 (0.5); 3.6216 (0.4); 3.3468 (16.0); 2.5346 (2.1); 2.5288 (4.2); 2.5227 (5.7); 2.5167 (4.2); 2.5107 (2.0); 2.0099 (0.5); 0.0206 (6.7) I.033: de1H NMR (400.1 MHz, d6-DMSO): δ= 8.6039 (5.7); 8.4049 (5.7); 8.3989 (5.6); 7.9524 (1.9); 7.8094 (3.4); 7.8031 (3.3); 7.7875 (3.6); 7.7812 (3.6); 7.7416 (3.7); 7.7198 (16.0); 7.7076 (15.3); 7.6857 (3.4); 7.3552 (4.8); 7.3391 (14.7); 7.3335 (14.2); 7.3228 (3.4); 7.3148 (9.1); 7.2953 (3.2); 7.2397 (2.5); 7.2224 (3.2); 7.2093 (1.0); 7.2055 (1.3); 6.6334 (4.8); 6.6116 (4.7); 4.5462 (7.8); 4.5312 (7.6); 3.9574 (3.9); 3.9115 (5.0); 3.5828 (3.2); 3.5370 (2.6); 3.3040 (156.0); 2.8897 (13.2); 2.7309 (11.4); 2.5085 (16.0); 2.5043 (31.0); 2.4999 (41.2); 2.4955 (30.1); 1.2353 (0.6); 0.0078 (1.3); -0.0002 (25.7) Petition 870260051039, dated 05 / 28 / 2026, pp. 123 / 314 120 / 149 1.034: 1H NMR (400.1 MHz, CDCI3): δ= 8.2448(1.3); 8.2401 (1.4); 8.2323(1.3); 8.2276(1.3); 8.0111 (0.6); 7.6038 (1.1); 7.6012 (1.1); 7.5962 (0.4); 7.5871 (1.2); 7.5829 (1.1); 7.5175 (0.4); 7.4999 (1.6); 7.4802 (3.2); 7.4729 (5.2); 7.2879 (0.4); 7.2586 (44.6); 7.0075 (1.4); 6.9949 (1.7); 6.9893 (1.4); 6.9767 (1.3); 3.9700 (0.4); 3.9529 (16.0); 3.9252 (2.4); 3.7470 (1.5); 3.7028 (2.4); 3.6602 (0.4); 3.5670 (0.8); 3.5493 (1.6); 3.5024 (1.0); 2.9547 (4.6); 2.8802 (4.1); 1.5389 (27.0); 1.2567 (3.2); 0.8804 (0.6); 0.8626 (0.3); 0.0078 (3.0); -0.0002 (55.6); -0.0082 (2.6) 1,035: RMN de1H (400.1 MHz, CDCI3): δ= 8.2057 (1.3); 8,2010 (1.4); 8.1932 (1.3); 8.1885 (1.3); 8.0050 (1.0); 7.7321 (2.6); 7.7278 (1.1); 7.7156 (1.4); 7.7109 (4.2); 7.6457 (4.6); 7.6384 (1.9); 7.6246 (4.0); 7.6200 (1.9); 7.2592 (9.0); 7.0122 (1.4); 6.9997 (1.4); 6.9940 (1.4); 6.9815 (1.3); 3.9957 (1.1); 3.9816 (16.0); 3.8251 (1.4); 3.7804 (2.1); 3.5885 (1.4); 3.5438 (1.0); 2.9526 (7.2); 2.8762 (6.2); 1.5744 (3.5); 1.2570 (1.4); 0.0077 (0.6); -0.0002 (10.7); -0.0082 (0.5) 1,036: RMN de1H (400.1 MHz, d6-DMSO): δ= 8.6618 (3.8); 8.2299 (3.3); 8.2085 (3.8); 7.9525 (1.0); 7.8422 (4.0); 7.8388 (2.8); 7.8204 (4.9); 7.7994 (1.6); 7.6685 (2.3); 7.6503 (1.8); 6.8429 (2.3); 6.8226 (2.2); 4.0040 (1.6); 3.9766 (16.0); 3.9578 (2.0); 3.6255 (1.2); 3.5789 (1.0); 3.3023 (31.6); 2.8903 (7.0); 2.7311 (5.9); 2.5091 (3.8); 2.5048 (7.5); 2.5003 (9.9); 2.4959 (7.3); 0.0079 (0.4); 0.0002 (9.0); -0.0083 (0.5) I.037: 1H NMR (300.2 MHz, d6-DMSO): δ= 8.7293 (2.3); 8.3012 (2.4); 8.2702 (2.6); 8.2388 (3.3); 8.2105 (3.9); 7.9100 (3.8); 7.8819 (3.3); 7.3954 (2.8); 7.3644 (2.6); 4.1174 (16.0); 4.0565 (1.5); 3.9946 (2.0); 3.6670 (1.3); 3.6047 (1.0); 3.3508 (15.3); 2.9103 (0.3); 2.5282 (5.2); 2.5223 (7.0); 2.5165 (5.3); 0.0189 (3.4) Petition 870260051039, dated 05 / 28 / 2026, pp. 124 / 314 121 / 149 1.038: 1Η NMR (300.2 MHz, d6-DMSO): δ= 8.7450 (0.9); 8.5349 (0.9); 8.5174 (0.9); 8.0351 (1.2); 8.0065 (1.8); 7.9734 (1.1); 7.9700 (1.2); 7.9029 (1.8); 7.8744 (1.2); 7.8675 (0.9); 7.8622 (0.7); 7.8499 (0.7); 7.8445 (0.6); 4.0603 (0.8); 3.9986 (0.8); 3.6649 (0.5); 3.6032 (0.4); 3.3516 (16.0); 2.5339 (2.0); 2.5281 (4.1); 2.5220 (5.4); 2.5160 (3.9); 2.5102 (1.9); 2.0093 (1.2); 1.2179 (0.3); 1.1942 (0.7); 1.1703 (0.4); 0.0195 (4.7) 1.039: de 1 H NMR (400.1 MHz, CDCl 3 ): δ= 8.4185 (2.0); 8.4125 (2.0); 7.9905 (1.1); 7.9706 (2.0); 7.9508 (1.2); 7.8095 (1.4); 7.8030 (1.4); 7.7879 (1.4); 7.7814 (1.4); 7.4063 (1.4); 7.4020 (1.5); 7.3857 (1.3); 7.3815 (1.4); 7.3300 (1.4); 7.3258 (1.2); 7.2990 (1.4); 7.2949 (1.3); 7.2590 (10.1); 6.8600 (2.1); 6.8384 (2.0); 3.9965 (16.0); 3.8584 (0.8); 3.8530 (0.8); 3.8121 (1.4); 3.8068 (1.3); 3.6792 (0.7); 3.6623 (1.2); 3.6590 (1.2); 3.6159 (0.6); 3.6126 (0.6); 2.9563 (0.4); 1.5648 (3.3); 1.2850 (0.4); 1.2571 (2.0); 0.8807 (0.4); -0.0002 (11.6) I. 040: 1H NMR (400.1 MHz, CDCI3): δ= 8.3334 (4.8); 8.3202 (5.0); 7.5947 (1.2); 7.5742 (8.6); 7.5604 (10.3); 7.5471 (4.4); 7.5175 (0.8); 7.4024 (3.0); 7.3987 (3.0); 7.3943 (2.3); 7.3892 (2.9); 7.3855 (2.8); 7.2587 (127.7); 7.1513 (5.3); 6.9946 (0.6); 4.0862 (0.5); 3.7542 (3.8); 3.7097 (5.9); 3.5552 (4.4); 3.5079 (2.5); 2.9558 (1.0); 2.8815 (0.8); 2.8029 (0.4); 2.6025 (0.4); 1.5837 (0.8); 1.5363 (70.0); 1.4034 (0.5); 1.3704 (0.7); 1.3580 (0.6); 1.3329 (1.1); 1.2852 (2.8); 1.2565 (16.0); 1.1105 (0.6); 1.0984 (0.6); 1.0646 (0.6); 0.9973 (0.4); 0.8974 (1.5); 0.8810 (3.1); 0.8535 (2.0); 0.8366 (1.7); 0.7338 (0.3); 0.1457 (0.6); 0.0078 (7.2); 0.0002 (150.8); -0.0541 (0.4); -0.0645 (0.4); -0.1501 (0.7) Petition 870260051039, dated 05 / 28 / 2026, pp. 125 / 314 122 / 149 1.041: 1H NMR (300.2 MHz, d6-DMSO): δ= 8.7007 (0.8); 8.6837 (0.9); 8.6720 (1.8); 8.6413 (1.4); 7.7046 (1.2); 7.6767 (1.5); 7.5204 (0.8); 7.5038 (0.8); 7.3180 (1.5); 7.2900 (1.3); 7.2801 (0.5); 7.2612 (0.6); 7.2505 (1.1); 7.2314 (1.0); 7.2217 (1.2); 7.1917 (1.3); 7.1619 (0.4); 3.9830 (0.5); 3.9197 (0.6); 3.5785 (0.4); 3.5159 (0.4); 3.3518 (16.0); 2.5911 (0.4); 2.5339 (13.5); 2.5280 (27.3); 2.5220 (36.8); 2.5160 (26.7); 2.5102 (12.8); 2.4612 (0.4); 2.0095 (1.0); 1.1948 (0.5); 0.0311 (1.2); 0.0203 (28.4); 0.0094 (1.2) 1,042: RMN de1H (300.2 MHz, d6-DMSO): δ= 8.7908(1.2); 8.7838(1.2); 8.7016(2.4); 8.4765(1.1); 8.4721 (1.2); 8.0113 (1.2); 7.9067 (0.6); 7.8985 (0.3); 7.8774 (4.4); 7.8674 (4.3); 7.8378 (0.6); 4.0438 (0.9); 3.9820 (1.2); 3.6536 (0.7); 3.5920 (0.5); 3.3433 (16.0); 2.5347 (3.1); 2.5286 (6.7); 2.5226 (9.3); 2.5165 (6.6); 2.5105 (3.1); 2.4085 (6.3); 0.0316 (0.4); 0.0208 (11.0); 0.0099 (0.4) 1,043: RMN de1H (300.2 MHz, d6-DMSO): δ= 8.7228 (1.1); 8.3757 (0.8); 8.3474 (1.0); 8.3373 (0.5); 8.3186 (0.5); 8.3075 (0.5); 8.2889 (0.5); 8.0598 (0.6); 8.0498 (0.6); 8.0368 (0.9); 8.0212 (0.6); 8.0145 (0.4); 8.0104 (0.4); 7.9144 (0.9); 7.8860 (0.8); 7.4241 (0.5); 7.3945 (0.9); 7.3648 (0.4); 4.0654 (0.3); 4.0038 (0.4); 3.3488 (16.0); 2.5342 (1.5); 2.5284 (3.0); 2.5224 (4.1); 2.5164 (3.0); 2.5106 (1.5); 0.0199 (4.0) 1.044: de 1 H NMR (300.2 MHz, CDCl 3 ): δ= 9.4019 (14.9); 9.0953 (16.0); 7.9468 (10.5); 7.9196 (15.0); 7.7496 (13.9); 7.7219 (11.7); 7.3006 (13.7); 3.8405 (5.0); 3.7810 (9.0); 3.6398 (7.0); 3.5803 (3.9); 2.0485 (13.5); 1.9803 (0.4); 1.7126 (2.1); 1.5553 (0.6); 1.5365 (0.4); 1.4942 (0.4); 1.2906 (0.8); 0.0361 (13.1) I.045: de1H NMR (400.1 MHz, d6-DMSO): δ= 9.4703 (12.9); 8.7275 (5.8); 8.0839 (4.3); 8.0632 (5.6); 7.9592 (3.4); 7.9348 (5.6); 7.9141 (4.4); 4.0393 (2.2); 3.9928 (2.8); 3.6587 (2.1); 3.6121 (1.6); 3.3192 (45.5); 2.8977 (16.0); 2.7383 (15.2); 2.5081 (13.7); 1.1626 (0.4) Petition 870260051039, dated 05 / 28 / 2026, page 126 / 314 123 / 149 1.046: 1Η NMR (400.1 MHz, d6-DMSO): δ= 9.0996 (12.8); 8.6977 (1.3); 7.9409 (3.6); 7.9200 (6.4); 7.8717 (6.3); 7.8510 (3.4); 4.0163 (2.2); 3.9698 (2.7); 3.6384 (1.9); 3.5916 (1.6); 3.3204 (25.9); 2.8973 (0.8); 2.7383 (0.8); 2.6866 (16.0); 2.5080 (9.2) 1.047: 1H NMR (300.2 MHz, d6-DMSO): δ= 8.3832 (0.6); 8.3548 (0.7); 8.2661 (0.4); 8.2610 (0.5); 8.2379 (0.6); 8.0645 (0.4); 8.0546 (0.4); 8.0399 (0.7); 8.0237 (0.5); 8.0174 (0.3); 7.9176 (0.7); 7.8893 (0.6); 7.5745 (0.6); 7.5496 (0.4); 4.0022 (0.3); 3.3490 (16.0); 2.5349 (1.3); 2.5288 (2.8); 2.5228 (3.9); 2.5167 (2.8); 2.5108 (1.3); 0.0206 (3.1) 1.048: 1H NMR (300.2 MHz, d6-DMSO): δ= 8.7910 (0.4); 8.7738 (0.4); 8.3206 (0.5); 8.3180 (0.5); 8.2668 (0.4); 8.2615 (0.5); 8.2391 (0.6); 8.2350 (0.4); 8.1187 (0.6); 8.0903 (0.8); 7.9227 (0.8); 7.8944 (0.6); 7.5517 (0.6); 7.5270 (0.5); 7.5139 (0.4); 4.0116 (0.4); 3.3475 (16.0); 2.5343 (1.7); 2.5284 (3.5); 2.5223 (4.7); 2.5163 (3.4); 2.5104 (1.6); 0.0204 (5.5) 1.049: de1H NMR (300.2 MHz, d6-DMSO): δ= 8.7713 (1.0); 8.0901 (3.8); 8.0614 (5.3); 7.9176 (5.3); 7.8890 (3.8); 7.6979 (16.0); 4.0626 (1.7); 4.0007 (2.3); 3.6756 (1.5); 3.6124 (1.1); 3.3484 (13.9); 2.5342 (5.6); 2.5283 (11.7); 2.5222 (15.9); 2.5161 (11.5); 2.5102 (5.4); 0.0307 (0.6); 0.0198 (17.2); 0.0088 (0.7) I.050: de1H NMR (400.2 MHz, d6-DMSO): δ= 8.7157 (2.8); 8.5969 (2.4); 8.5916 (3.2); 8.5684 (3.9); 8.5623 (2.7); 7.9552 (1.6); 7.8751 (3.5); 7.8542 (5.4); 7.7795 (5.5); 7.7585 (3.6); 4.0385 (1.9); 3.9921 (2.4); 3.6485 (1.6); 3.6017 (1.2); 3.3555 (40.3); 2.8933 (9.5); 2.7343 (8.5); 2.6222 (0.5); 2.5900 (16.0); 2.5108 (14.4); 2.5064 (18.1); 2.5020 (13.3); -0.0002 (0.4) Petition 870260051039, dated 05 / 28 / 2026, pp. 127 / 314 124 / 149 1.051: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.1420 (3.2); 8.1263 (2.9); 8.1120 (3.0); 8.0164 (4.0); 7.9952 (5.1); 7.9538 (2.6); 7.8325 (4.9); 7.8114 (4.2); 7.0814 (3.1); 7.0766 (3.2); 6.5555 (1.8); 6.5505 (1.8); 6.5411 (1.8); 6.5362 (1.7); 6.4358 (2.6); 4.0048 (2.2); 3.9585 (2.7); 3.6183 (3.0); 3.5715 (3.2); 3.5330 (2.0); 3.2397 (0.3); 2.8919 (16.0); 2.7327 (14.3); 2.5105 (19.2); 2.5061 (24.8); 2.5017 (18.7); 1.1598 (2.6); 1.0720 (2.1); -0.0002 (0.4) 1.052: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.7515 (4.8); 8.7376 (5.3); 8.7289 (5.4); 8.7144 (7.0); 8.7072 (14.8); 8.2717 (14.5); 8.2507 (16.0); 8.0620 (5.2); 8.0568 (5.3); 8.0346 (5.3); 8.0294 (5.1); 7.9567 (1.3); 7.8713 (15.9); 7.8503 (14.4); 7.3738 (2.9); 7.3683 (3.0); 7.3599 (3.4); 7.3531 (4.8); 7.3469 (3.2); 7.3383 (3.1); 7.3329 (2.6); 4.0296 (6.9); 3.9832 (8.6); 3.6415 (5.8); 3.5950 (4.6); 3.3439 (22.9); 2.8933 (7.6); 2.7345 (7.2); 2.6758 (0.4); 2.5111 (48.0); 2.5068 (59.8); 2.5026 (45.1); 2.3339 (0.3); 1.2295 (0.3); 1.2200 (0.3); 1.2097 (0.4); 1.2002 (0.4); 1.1839 (0.4); 1.1703 (0.5); 1.1535 (0.4); 1.1334 (0.4); 0.0077 (0.4); -0.0002 (8.7); 0.0084 (0.4) 1,053: RMN de1H (400.2 MHz, d6-DMSO): δ = 8.8894 (9.4); 8.7136 (10.4); 8.6288 (8.8); 8.6223 (9.1); 8.1941 (2.7); 8.1883 (4.0); 8.1834 (2.9); 8.1684 (2.8); 8.1628 (3.9); 8.1575 (2.8); 7.9570 (10.3); 7.9359 (16.0); 7.8695 (15.8); 7.8483 (10.1); 4.0253 (5.9); 3.9789 (7.5); 3.6422 (4.8); 3.5958 (3.8); 3.3536 (26.4); 3.3497 (26.7); 2.8934 (3.0); 2.7340 (2.7); 2.5113 (36.5); 2.5068 (46.6); 2.5024 (34.5); -0.0002 (6.2) I. 054: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.7022 (10.3); 8.6956 (16.0); 8.1928 (10.4); 8.1718 (14.5); 8.1617 (3.8); 8.1501 (3.7); 8.1393 (3.4); 7.9560 (1.7); 7.8944 (2.1); 7.8870 (2.2); 7.8725 (4.0); 7.8649 (4.8); 7.8572 (12.4); 7.8361 (10.9); 4.0197 (5.1); 3.9734 (6.4); 3.6315 (4.2); 3.5849 (3.4); 3.3539 (26.8); 3.3470 (26.6); 2.8929 (10.5); 2.7338 (9.6); 2.5107 (39.0); 2.5063 (49.6); 2.5019 (36.7); -0.0002 (7.5) Petition 870260051039, dated 05 / 28 / 2026, pp. 128 / 314 125 / 149 1.055: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.7121 (14.7); 8.2032 (14.1); 8.1822 (16.0); 8.1527 (1.7); 8.1330 (4.9); 8.1129 (6.0); 8.0927 (2.7); 8.0559 (5.3); 8.0499 (5.5); 8.0373 (3.6); 8.0310 (3.4); 7.9574 (1.9); 7.8763 (15.8); 7.8552 (14.1); 7.2154 (4.8); 7.2088 (5.0); 7.1955 (4.7); 7.1888 (4.6); 4.0280 (6.8); 3.9816 (8.4); 3.6375 (5.5); 3.5912 (4.5); 3.3459 (33.9); 2.8940 (11.3); 2.7352 (10.5); 2.6763 (0.3); 2.5118 (43.4); 2.5075 (54.6); 2.5031 (40.4); -0.0002 (4.2) 1.056: de1H NMR (400.2 MHz, d6-DMSO): δ= 9.0645 (6.2); 8.9438 (3.4); 8.9314 (3.4); 8.7261 (3.1); 7.9546 (2.6); 7.8664 (6.3); 7.8455 (7.1); 7.5478 (3.3); 7.5354 (3.4); 7.5200 (6.1); 7.4996 (5.4); 4.0390 (2.9); 3.9926 (3.6); 3.6386 (2.4); 3.5918 (2.0); 3.3755 (54.7); 3.3682 (70.3); 2.8938 (16.0); 2.7347 (14.3); 2.7338 (14.2); 2.5115 (27.3); 2.5071 (34.3); 2.5026 (25.0) 1.057:1H-RMN(400.2 MHz, d6-DMSO): δ= 8.7559 (0.4); 8.6613 (2.6); 8.6483 (2.6); 7.9975 (3.5); 7.9759 (5.9); 7.9554 (2.8); 7.8763 (4.9); 7.8553 (3.6); 7.8341 (1.8); 7.8300 (1.8); 7.8211 (1.8); 7.8169 (1.7); 4.4097 (6.1); 4.0287 (1.9); 3.9823 (2.4); 3.6423 (1.6); 3.5955 (1.3); 3.3654 (33.6); 2.8937 (16.0); 2.7348 (14.2); 2.7342 (14.2); 2.5120 (18.2); 2.5075 (23.3); 2.5031 (17.1) 1,058: RMN de1H (400.2 MHz, d6-DMSO): δ= 8.9910 (2.3); 8.9861 (2.2); 8.7092 (4.7); 8.2917 (1.7); 8.2869 (2.7); 8.2820 (1.5); 7.9537 (3.0); 7.9396 (2.7); 7.9186 (4.1); 7.8570 (4.3); 7.8361 (2.6); 4.5365 (4.4); 4.0217 (1.6); 3.9753 (2.0); 3.6361 (1.3); 3.5892 (1.1); 3.3342 (20.6); 2.8915 (16.0); 2.7321 (14.9); 2.5080 (41.3); 2.5036 (52.4); 2.4992 (39.0); 1.3408 (1.2); 1.3029 (1.2); -0.0002 (8.2); -0.0084 (0.4) I.059: RMN de1H (400.2 MHz, d6-DMSO): δ= 8.7582 (6.9); 8.6630 (3.0); 8.6407 (3.6); 8.4122 (4.8); 8.3946 (7.6); 8.3904 (6.7); 8.3738 (7.5); 7.9754 (7.6); 7.9547 (8.8); 4.0615 (3.3); 4.0152 (4.2); 3.6734 (2.6); 3.6268 (2.2); 3.3416 (14.5); 2.8944 (16.0); 2.7349 (14.6); 2.5114 (27.0); 2.5070 (34.6); 2.5025 (25.4); -0.0002 (5.4) Petition 870260051039, dated 05 / 28 / 2026, page 129 / 314 126 / 149 1.060: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.8425 (3.3); 8.8295 (3.4); 8.7360 (5.4); 8.5281 (4.1); 8.5254 (4.1); 8.1704 (2.2); 8.1661 (2.2); 8.1574 (2.2); 8.1531 (2.1); 8.0690 (4.7); 8.0480 (6.1); 7.9556 (2.6); 7.9103 (6.2); 7.8892 (4.9); 4.0388 (2.5); 3.9923 (3.1); 3.6537 (2.0); 3.6071 (1.6); 3.3438 (19.3); 2.8935 (16.0); 2.7339 (14.6); 2.5108 (18.6); 2.5064 (23.7); 2.5019 (17.6); -0.0002 (2.7) 1.061: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.8142 (2.4); 8.8108 (2.6); 8.8025 (2.5); 8.7991 (2.5); 8.7368 (4.4); 8.1891 (2.1); 8.1857 (2.2); 8.1690 (2.5); 8.1656 (2.4); 7.9543 (2.7); 7.9323 (4.6); 7.9113 (6.5); 7.8813 (2.1); 7.8696 (2.1); 7.8613 (1.9); 7.8495 (1.8); 7.8028 (6.4); 7.7818 (4.8); 4.0511 (2.4); 4.0047 (3.0); 3.6614 (2.0); 3.6148 (1.6); 3.3457 (23.3); 2.8925 (16.0); 2.7327 (14.3); 2.5095 (19.1); 2.5051 (24.5); 2.5006 (18.1); -0.0002 (2.5) 1,062: RMN de1H (400.2 MHz, d6-DMSO): δ= 8.9641 (6.3); 8.8752 (4.0); 8.8626 (4.1); 8.7400 (4.0); 8.0299 (3.3); 8.0175 (3.2); 7.9543 (2.7); 7.9382 (4.7); 7.9172 (6.6); 7.8179 (6.6); 7.7969 (4.8); 4.0505 (2.4); 4.0040 (3.0); 3.6627 (2.0); 3.6161 (1.6); 3.3484 (37.6); 2.8928 (16.0); 2.7338 (14.2); 2.5100 (18.9); 2.5056 (24.1); 2.5011 (17.7); -0.0002 (0.4) 1,063: RMN de1H (400.2 MHz, d6-DMSO): δ= 8.9495 (3.2); 8.9374 (3.3); 8.7281 (4.8); 8.5934 (5.0); 8.3008 (5.4); 8.2796 (6.1); 7.9557 (2.6); 7.8952 (6.0); 7.8739 (8.0); 7.8638 (2.9); 7.8611 (2.7); 4.0347 (2.5); 3.9883 (3.1); 3.6458 (2.1); 3.5992 (1.7); 3.3649 (71.3); 2.8942 (16.0); 2.7350 (14.3); 2.5125 (18.7); 2.5081 (24.0); 2.5036 (17.8) I. 064: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.6872 (2.4); 8.2964 (1.9); 8.2940 (2.0); 8.2852 (2.0); 8.2828 (2.0); 8.0226 (3.7); 8.0015 (4.6); 7.9547 (1.8); 7.8015 (4.4); 7.7804 (3.6); 7.6187 (1.6); 7.5996 (2.0); 7.5046 (0.5); 7.4294 (1.6); 7.4180 (1.6); 7.4084 (1.4); 7.3971 (1.3); 4.0040 (1.8); 3.9670 (0.4); 3.9577 (2.2); 3.8807 (16.0); 3.6213 (1.4); 3.5753 (1.2); 3.3475 (17.4); 2.8913 (11.1); 2.7328 (10.0); 2.5091 (14.0); 2.5047 (17.9); 2.5002 (13.2); -0.0002 (1.6) Petition 870260051039, dated 05 / 28 / 2026, pp. 130 / 314 127 / 149 1.065: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.7266(1.9); 8.5856 (6.7); 8.5727 (7.0); 7.9548(1.0); 7.9324 (5.6); 7.9111 (16.0); 7.8896 (15.2); 7.8684 (5.5); 7.8036 (7.7); 7.6449 (4.2); 7.6413 (4.1); 7.6321 (4.2); 7.6285 (3.9); 5.5110 (2.5); 4.6476 (8.1); 4.6373 (7.9); 4.0288 (4.2); 3.9825 (5.2); 3.6406 (3.0); 3.5941 (2.4); 3.3583 (67.6); 2.8921 (5.8); 2.7333 (5.2); 2.5103 (34.8); 2.5059 (44.4); 2.5015 (32.4); -0.0002 (1.0) 1.066: de1H NMR (400.2 MHz, d6-DMSO): δ= 8.9767 (5.2); 8.9725 (5.7); 8.9646 (5.7); 8.9604 (5.6); 8.8643 (0.3); 8.4844 (5.0); 8.4802 (5.3); 8.4646 (5.5); 8.4604 (5.4); 8.4084 (0.4); 7.9909 (7.6); 7.9742 (4.6); 7.9695 (16.0); 7.9259 (14.9); 7.9090 (3.3); 7.9046 (7.9); 7.6762 (5.4); 7.6641 (5.2); 7.6564 (5.1); 7.6443 (5.1); 4.0349 (4.2); 3.9885 (5.4); 3.6619 (3.7); 3.6151 (3.0); 3.3345 (8.5); 2.8913 (1.4); 2.7317 (1.1); 2.6724 (0.4); 2.5259 (1.2); 2.5124 (24.8); 2.5081 (49.5); 2.5035 (64.7); 2.4990 (48.5); 2.4946 (24.9); 2.3303 (0.4); -0.0002 (2.4) 1,067: RMN de1H (400.2 MHz, d6-DMSO): δ= 9.2201 (16.0); 9.2170 (16.0); 8.7817 (0.7); 8.7686 (0.6); 7.9669 (7.8); 7.9460 (13.2); 7.8864 (12.9); 7.8655 (7.7); 7.7622 (0.6); 4.0186 (4.4); 3.9722 (5.7); 3.6455 (3.6); 3.5989 (2.9); 3.3326 (20.4); 3.1832 (0.4); 2.8919 (2.1); 2.7323 (2.0); 2.6725 (0.4); 2.5119 (26.4); 2.5079 (49.4); 2.5036 (62.8); 2.4992 (46.2); 2.3304 (0.4); -0.0002 (1.8) I.068: RMN de1H (400.2 MHz, d6-DMSO): δ= 10.0753 (3.6); 8.9227 (1.0); 8.9102 (1.1); 8.2633 (1.2); 8.2601 (1.2); 8.1277 (0.8); 8.1230 (0.7); 8.1149 (0.8); 8.1102 (0.7); 8.0482 (1.5); 8.0269 (2.0); 7.9535 (2.4); 7.9312 (0.4); 7.9033 (2.2); 7.8821 (1.8); 7.8615 (0.4); 7.8457 (0.4); 4.0222 (0.8); 3.9758 (1.0); 3.9292 (0.4); 3.6666 (0.8); 3.6202 (0.6); 3.3357 (4.0); 2.8912 (16.0); 2.7322 (13.7); 2.7313 (13.7); 2.5253 (0.8); 2.5119 (15.1); 2.5076 (29.1); 2.5031 (37.3); 2.4985 (27.3); 2.4941 (13.6); 1.8528 (1.2); -0.0002 (1.4) Petition 870260051039, dated 05 / 28 / 2026, pp. 131 / 314 128 / 149 1.069: 1Η NMR (400.2 MHz, d6-DMSO): δ= 9.9940 (7.7); 8.8658 (2.3); 8.8621 (2.6); 8.8543 (2.4); 8.8506 (2.5); 8.7476 (0.3); 7.9625 (2.1); 7.9589 (2.5); 7.9528 (2.6); 7.9430 (2.6); 7.9397 (2.5); 7.8149 (5.0); 7.7941 (6.2); 7.7771 (2.6); 7.7656 (2.5); 7.7576 (2.1); 7.7460 (2.1); 7.5723 (6.0); 7.5515 (5.3); 4.0213 (2.3); 3.9748 (2.9); 3.6381 (1.9); 3.5916 (1.6); 3.3329 (12.1); 2.8907 (16.0); 2.7310 (14.1); 2.5070 (28.9); 2.5026 (37.9); 2.4981 (28.4); -0.0002 (1.2) 1.070: 1H NMR (400.2 MHz, d6-DMSO): δ= 10.1764 (2.0); 8.9886 (0.9); 8.9766 (0.9); 8.7363 (0.4); 8.4980 (1.2); 8.3060 (1.4); 8.2848 (1.6); 7.9534 (2.6); 7.9064 (1.6); 7.8853 (1.6); 7.8699 (0.4); 7.8579 (0.5); 7.8373 (0.4); 7.8131 (0.8); 7.8106 (0.8); 7.8012 (0.8); 7.7985 (0.7); 4.0371 (0.7); 3.9909 (0.9); 3.9519 (0.4); 3.6526 (0.6); 3.6054 (0.5); 3.3339 (28.0); 2.8910 (16.0); 2.7316 (14.3); 2.5118 (14.7); 2.5076 (27.8); 2.5031 (35.5); 2.4986 (26.2); 2.4943 (13.4); 1.9089 (0.9); 0.0002 (1.0) 1,071: RMN de1H (300.2 MHz, d6-DMSO): δ= 8.0875 (1.2); 8.0589 (1.7); 8.0096 (1.4); 7.9085 (1.6); 7.8801 (1.2); 7.7501 (1.3); 4.0585 (0.5); 3.9960 (0.7); 3.6700 (0.5); 3.6086 (0.3); 3.3465 (16.0); 2.5343 (5.5); 2.5283 (11.8); 2.5222 (16.4); 2.5161 (11.9); 2.5102 (5.5); 0.0314 (0.6); 0.0205 (17.8); 0.0095 (0.6) I.072: RMN de1H (300.2 MHz, d6-DMSO): δ= 9.1984 (3.1); 9.1913 (3.2); 8.7395 (8.6); 8.4923 (1.6); 8.4867 (1.6); 8.4651 (1.8); 8.4591 (1.8); 8.0606 (3.5); 8.0332 (3.2); 8.0122 (4.2); 7.9836 (8.3); 7.9253 (8.2); 7.8967 (4.1); 4.0615 (2.5); 3.9999 (3.2); 3.6755 (1.9); 3.6131 (1.4); 3.3493 (16.0); 2.5344 (6.3); 2.5284 (13.6); 2.5223 (18.6); 2.5162 (13.4); 2.5103 (6.2); 2.0094 (1.1); 1.1944 (0.6); 0.0304 (0.9); 0.0196 (25.5); 0.0086 (0.8) Petition 870260051039, dated 05 / 28 / 2026, page 132 / 314 129 / 149 1.073: 1Η NMR (300.2 MHz, d6-DMSO): δ= 8.7355 (1.1); 8.5985 (2.2); 8.5899 (2.3); 8.1679 (2.7); 8.1593 (2.7); 7.8851 (2.4); 7.8568 (3.0); 7.6855 (3.2); 7.6572 (2.3); 4.0576 (1.0); 3.9956 (1.3); 3.6598 (0.8); 3.5963 (0.6); 3.3467 (16.0); 2.5343 (5.7); 2.5283 (12.1); 2.5222 (16.6); 2.5161 (11.8); 2.5102 (5.4); 0.0310 (0.8); 0.0293 (0.4); 0.0277 (0.5); 0.0202 (23.1); 0.0125 (0.6); 0.0108 (0.6); 0.0093 (0.8) 1.074: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.6918 (0.8); 8.1378 (0.6); 7.9901 (2.0); 7.9857 (2.1); 7.9778 (2.1); 7.9735 (2.0); 7.9523 (2.6); 7.8093 (4.7); 7.7884 (5.8); 7.5742 (5.7); 7.5533 (4.8); 7.3837 (2.0); 7.3793 (2.0); 7.3654 (2.2); 7.3610 (2.0); 6.6971 (2.1); 6.6848 (2.1); 6.6788 (2.1); 6.6665 (2.0); 5.6802 (3.9); 3.9850 (2.2); 3.9386 (2.8); 3.6065 (1.8); 3.5600 (1.5); 3.3524 (0.7); 2.8903 (16.0); 2.7310 (14.1); 2.5074 (17.0); 2.5030 (21.8); 2.4985 (16.0); 2.4944 (8.0); -0.0002 HZ 1.075: NMR de1H (500.1 MHz, CDCI3): δ= 8.1292 (3.9); 8.1263 (4.0); 8.1196 (4.0); 8.1177 (3.9); 7.7696 (4.0); 7.7668 (4.2); 7.7593 (5.2); 7.7544 (5.4); 7.7505 (4.8); 7.7411 (16.0); 7.7309 (15.1); 7.7127 (4.5); 7.2504 (2.2); 7.2124 (1.7); 7.1965 (5.4); 7.1842 (8.9); 7.1748 (4.7); 7.1687 (10.0); 7.1606 (3.1); 7.1536 (2.4); 7.1376 (0.8); 7.1283 (3.6); 7.1185 (3.6); 7.1121 (3.5); 7.1023 (3.3); 3.7221 (4.1); 3.7130 (0.7); 3.6888 (5.6); 3.5104 (4.2); 3.4769 (3.2); 3.4688 (6.8); 1.9837 (2.2); 1.2579 (0.3); 1.2466 (0.5); 1.2324 (0.9); 1.2184 (0.5); -0.0002 (1.7) 1.076: 1H NMR (500.1 MHz, CDCI3): δ= 9.0838 (9.8); 9.0739 (9.8); 8.5914 (14.6); 8.5746 (14.7); 7.8123 (16.0); 7.7956 (14.8); 7.5686 (11.3); 7.5587 (11.0); 7.2598 (10.9); 3.7940 (8.0); 3.7586 (11.2); 3.5988 (7.6); 3.5633 (5.3); 2.0036 (3.8); 1.2551 (0.9); -0.0002 (7.3) I. 077: 1H NMR (500.1 MHz, d6-DMSO): δ= 8.7151 (4.5); 7.7659 (16.0); 7.7489 (0.8); 3.9699 (1.7); 3.9329 (2.1); 3.6104 (1.4); 3.5732 (1.2); 3.1739 (0.4); 2.5057 (1.3); -0.0002 (0.6) Petition 870260051039, dated 05 / 28 / 2026, pp. 133 / 314 130 / 149 1.078: 1H NMR (500.1 MHz, CDCI3): δ= 8.7196 (0.4); 8.6952 (3.6); 7.7637 (1.2); 7.7476 (1.4); 7.5891 (1.4); 7.5729 (1.3); 7.2614 (2.5); 3.7681 (0.4); 3.7339 (0.6); 3.5803 (0.5); 3.5454 (0.4); 3.4946 (0.6); 1.6661 (16.0); -0.0002 (2.3) 1,079: RMN de1H (400.2 MHz, d6-DMSO): δ= 8.7147 (2.2); 8.4831 (6.4); 8.4783 (6.9); 8.4712 (6.9); 8.4664 (6.7); 7.9469 (6.3); 7.9421 (6.4); 7.9280 (7.2); 7.9232 (6.7); 7.8547 (12.8); 7.8501 (4.7); 7.8382 (5.4); 7.8336 (15.7); 7.6268 (16.0); 7.6221 (5.3); 7.6101 (5.0); 7.6056 (13.2); 7.5791 (6.9); 7.5673 (6.7); 7.5602 (6.4); 7.5483 (6.3); 4.0255 (5.8); 3.9791 (7.3); 3.6344 (4.3); 3.5872 (3.5); 3.3401 (65.4); 2.8916 (5.6); 2.7328 (4.6); 2.7317 (4.5); 2.6728 (0.4); 2.5262 (1.4); 2.5129 (27.7); 2.5084 (54.4); 2.5039 (69.8); 2.4993 (49.3); 2.4948 (23.4); 2.3307 (0.4); 1.2396 (0.4); -0.0002 (3.5) 1,080: RMN de1H (400.2 MHz, d6-DMSO): δ = 8.7480 (9.4); 8.7423 (9.5); 8.7086 (3.6); 8.2185 (14.0); 8.1972 (16.0); 8.1318 (5.6); 8.1105 (10.8); 8.0701 (8.2); 8.0639 (7.8); 8.0487 (4.3); 8.0424 (4.3); 7.8658 (15.7); 7.8446 (14.2); 4.0210 (6.4); 3.9747 (8.1); 3.6319 (5.1); 3.5855 (4.1); 3.3433 (65.4); 2.8928 (0.4); 2.7336 (0.3); 2.6745 (0.4); 2.5142 (24.8); 2.5102 (47.5); 2.5058 (60.9); 2.5013 (44.2); 2.3327 (0.4); 1.2353 (0.4); -0.0002 (3.4) I. 081: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.8268 (7.0); 8.8204 (7.0); 8.7137 (1.9); 8.2605 (4.1); 8.2540 (4.0); 8.2396 (4.4); 8.2330 (4.4); 7.9053 (5.7); 7.8841 (16.0); 7.8599 (15.5); 7.8386 (5.8); 7.6551 (7.2); 7.6342 (6.8); 4.0154 (4.7); 3.9690 (6.0); 3.6333 (3.8); 3.5865 (3.0); 3.3403 (32.5); 2.8921 (0.4); 2.7327 (0.4); 2.5092 (34.9); 2.5049 (44.4); 2.5005 (32.3); 1.2359 (0.4); 0.0002 (2.3) Petition 870260051039, dated 05 / 28 / 2026, pp. 134 / 314 131 / 149 1.082: 1Η NMR (400.2 MHz, d6-DMSO): δ = 8.7241 (0.9); 8.6959 (0.9); 8.6823 (11.0); 8.6691 (11.0); 8.2718 (14.1); 8.2507 (15.8); 8.2376 (10.6); 8.2332 (10.6); 7.9547 (2.4); 7.8650 (15.7); 7.8439 (14.4); 7.5659 (6.4); 7.5614 (6.3); 7.5527 (6.3); 7.5482 (6.0); 4.0250 (6.2); 3.9786 (7.8); 3.6354 (5.3); 3.5888 (4.3); 3.3426 (56.3); 2.8922 (16.0); 2.7504 (0.3); 2.7331 (14.2); 2.6782 (0.4); 2.6739 (0.5); 2.6695 (0.4); 2.5093 (64.8); 2.5049 (81.8); 2.5005 (59.5); 2.3361 (0.4); 2.3318 (0.5); 2.3275 (0.4); 1.2360 (0.8); -0.0002 (3.1) 1,083: RMN de1H (400.2 MHz, d6-DMSO): δ= 9.2059 (16.0); 7.9808 (3.8); 7.9596 (6.0); 7.8887 (5.9); 7.8676 (3.7); 4.0175 (2.0); 3.9710 (2.4); 3.6393 (1.6); 3.5929 (1.3); 3.3372 (55.8); 2.8914 (0.6); 2.7319 (0.5); 2.6720 (0.4); 2.5250 (1.4); 2.5118 (24.2); 2.5075 (46.5); 2.5031 (59.3); 2.4986 (42.5); 2.4943 (20.8); 2.3300 (0.4); 1.2391 (0.6); -0.0002 (3.0) 1,084: RMN de1H (400.2 MHz, d6-DMSO): δ= 8.1698 (1.2); 8.1567 (1.2); 7.8855 (1.2); 7.8642 (2.7); 7.8281 (2.6); 7.8068 (1.2); 6.9140 (0.8); 6.9107 (1.0); 6.9009 (0.7); 6.8976 (1.0); 6.8843 (1.6); 3.9920 (0.7); 3.9457 (0.9); 3.6294 (0.7); 3.5829 (0.5); 3.3308 (3.7); 3.0949 (16.0); 2.8904 (0.7); 2.7308 (0.6); 2.5110 (11.1); 2.5067 (21.7); 2.5022 (27.9); 2.4976 (20.0); 2.4932 (9.8); -0.0002 (1.2) I.085: de1H NMR (400.2 MHz, d6-DMSO): δ= 8.6848 (1.3); 8.1997 (3.0); 8.1951 (3.2); 8.1874 (3.2); 8.1829 (3.0); 7.8271 (3.0); 7.8225 (3.0); 7.8086 (3.4); 7.8040 (3.3); 7.7942 (5.5); 7.7734 (9.2); 7.7163 (9.4); 7.6955 (5.4); 7.1196 (3.0); 7.1072 (3.0); 7.1012 (3.0); 7.0888 (2.8); 4.4053 (2.4); 4.3877 (7.6); 4.3701 (7.6); 4.3526 (2.4); 3.9980 (3.1); 3.9518 (4.0); 3.6172 (2.5); 3.5706 (2.0); 3.3390 (21.9); 2.8916 (0.6); 2.7329 (0.5); 2.5261 (0.7); 2.5128 (13.4); 2.5086 (25.0); 2.5042 (31.6); 2.4998 (22.7); 1.3175 (7.9); 1.2999 (16.0); 1.2824 (7.6); -0.0002 (1.1) Petition 870260051039, dated 05 / 28 / 2026, page 135 / 314 132 / 149 1.086: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.7198 (1.0); 8.2494 (4.2); 8.2359 (4.4); 7.9548 (1.9); 7.9284 (5.0); 7.9071 (8.5); 7.8473 (8.5); 7.8260 (5.1); 7.3651 (3.0); 7.3613 (3.1); 7.3516 (2.9); 7.3477 (3.0); 7.1607 (5.0); 7.1583 (4.9); 4.3860 (2.1); 4.3685 (6.8); 4.3509 (6.9); 4.3333 (2.1); 4.0151 (2.9); 3.9687 (3.6); 3.6282 (2.2); 3.5812 (1.8); 3.3419 (30.7); 2.8921 (13.3); 2.7332 (11.2); 2.5271 (0.6); 2.5138 (12.9); 2.5094 (25.3); 2.5049 (32.7); 2.5003 (23.4); 2.4959 (11.4); 1.3647 (7.7); 1.3471 (16.0); 1.3295 (7.4); -0.0002 (1.1) 1.087: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.7002 (0.7); 8.2628 (1.3); 8.2482 (1.3); 8.2414 (1.4); 8.2268 (1.2); 7.9535 (2.0); 7.8109 (3.6); 7.7902 (4.5); 7.5491 (3.6); 7.5290 (3.1); 7.1299 (1.3); 7.1154 (1.3); 7.1078 (1.4); 7.0933 (1.2); 4.0061 (1.7); 3.9597 (2.2); 3.8721 (16.0); 3.6195 (1.5); 3.5731 (1.2); 3.3430 (28.4); 2.8916 (11.4); 2.7323 (10.5); 2.5084 (15.4); 2.5042 (20.0); 2.5001 (15.9); -0.0002 (0.4) 1,088: RMN de1H (400.2 MHz, d6-DMSO): δ= 9.2381 (6.2); 9.2255 (6.4); 8.7528(4.9); 8.1133 (7.1); 8.1006 (6.9); 8.0105 (7.1); 7.9896 (16.0); 7.9556 (15.6); 7.9347 (7.3); 4.0630 (5.0); 4.0166 (6.3); 3.6672 (4.3); 3.6206 (3.5); 3.3406 (105.3); 2.8920 (1.1); 2.7325 (1.0); 2.6733 (0.4); 2.5080 (47.0); 2.5042 (58.9); 2.3313 (0.4); 1.2387 (0.6); -0.0002 (1.9) I.089: RMN de1H (400.2 MHz, d6-DMSO): δ = 8.7721 (1.9); 8.7687 (2.0); 8.7605 (2.0); 8.7570 (2.0); 8.7240 (1.4); 7.9535 (2.4); 7.9266 (1.6); 7.9080 (1.9); 7.8661 (4.5); 7.8455 (5.2); 7.7145 (1.4); 7.7027 (1.4); 7.6950 (1.2); 7.6831 (1.1); 7.5391 (4.9); 7.5185 (4.4); 6.9906 (1.3); 6.8563 (2.8); 6.7220 (1.4); 4.0250 (2.0); 3.9786 (2.6); 3.6369 (1.7); 3.5903 (1.4); 3.3334 (10.8); 2.8912 (16.0); 2.7317 (14.3); 2.5076 (20.1); 2.5033 (25.7); 2.4988 (18.8); -0.0002 (1.0) Petition 870260051039, dated 05 / 28 / 2026, page 136 / 314 133 / 149 1,090: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.6089 (0.7); 8.5962 (0.7); 7.9459 (0.8); 7.9249 (1.3); 7.8635 (1.3); 7.8426 (0.8); 7.7203 (0.8); 7.5694 (0.5); 7.5656 (0.5); 7.5568 (0.5); 7.5524 (0.5); 4.0184 (0.4); 3.9722 (0.6); 3.6356 (0.4); 3.5892 (0.3); 3.3272 (24.8); 2.8906 (1.1); 2.7310 (1.0); 2.6708 (0.4); 2.5104 (26.1); 2.5063 (49.1); 2.5019 (62.0); 2.4975 (44.3); 2.4933 (21.6); 2.3288 (0.4); 1.3804 (16.0); 1.2394 (0.6); -0.0003 (2.2) 1.091: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.7128(1.3); 8.2458 (4.4); 8.2323 (4.5); 7.9553 (2.0); 7.9328 (5.1); 7.9116 (8.5); 7.8475 (8.4); 7.8263 (5.1); 7.3656 (3.0); 7.3618 (3.1); 7.3521 (2.9); 7.3482 (3.0); 7.1710 (5.2); 7.1685 (4.9); 4.2791 (4.2); 4.2624 (8.8); 4.2456 (4.2); 4.0168 (2.9); 3.9705 (3.7); 3.6292 (2.2); 3.5825 (1.8); 3.3390 (14.5); 2.8923 (14.1); 2.7336 (11.9); 2.6290 (0.4); 2.5272 (0.6); 2.5140 (11.4); 2.5097 (22.3); 2.5052 (28.7); 2.5006 (20.5); 2.4962 (9.9); 1.7995 (0.5); 1.7814 (2.3); 1.7640 (4.6); 1.7459 (4.7); 1.7285 (2.4); 1.7106 (0.6); 1.3098 (0.4); 1.0072 (7.9); 0.9888 (16.0); 0.9701 (7.1); -0.0002 (1.2) 1.092: de1H NMR (400.2 MHz, d6-DMSO): δ= 8.7131 (0.9); 8.3182 (2.3); 8.3136 (2.5); 8.3060 (2.5); 8.3014 (2.5); 8.0473 (2.2); 8.0428 (2.3); 8.0285 (2.5); 8.0240 (2.4); 7.9518 (3.5); 7.8528 (4.9); 7.8318 (6.5); 7.7697 (4.2); 7.6919 (6.6); 7.6708 (5.1); 7.5881 (2.0); 7.4354 (2.4); 7.4232 (2.4); 7.4167 (2.4); 7.4044 (2.3); 4.0126 (2.4); 3.9662 (3.0); 3.6335 (1.8); 3.5870 (1.5); 3.3379 (19.2); 2.8915 (16.0); 2.7324 (13.7); 2.6296 (0.4); 2.5260 (0.5); 2.5127 (10.8); 2.5083 (21.4); 2.5038 (27.7); 2.4993 (20.0); 2.4949 (9.8); -0.0002 (1.0) I. 093: 1H NMR (400.2 MHz, d6-DMSO): δ= 8.7286 (2.2); 8.3634 (2.8); 8.3490 (2.8); 8.3431 (3.1); 8.3288 (2.6); 7.9541 (2.2); 7.8801 (8.3); 7.8592 (10.4); 7.6685 (6.6); 7.6482 (5.5); 7.5433 (3.2); 7.5290 (3.2); 7.5219 (3.3); 7.5075 (3.0); 4.0229 (3.9); 3.9764 (4.9); 3.6355 (3.1); 3.5890 (2.5); 3.3334 (21.4); 2.8918 (16.0); 2.7325 (14.0); 2.5125 (21.2); 2.5082 (40.9); 2.5037 (52.4); 2.4992 (37.7); 2.4949 (18.5); 1.2392 (0.4); -0.0002 (1.9) Petition 870260051039, dated 05 / 28 / 2026, pp. 137 / 314 134 / 149 1.094: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.8139 (4.7); 8.8048 (4.5); 8.8024 (4.6); 8.7321 (0.4); 7.9772 (3.8); 7.9575 (5.1); 7.8480 (11.1); 7.8373 (5.4); 7.8271 (16.0); 7.8179 (3.9); 7.8060 (3.2); 7.5053 (10.8); 7.4847 (9.7); 4.0301 (4.9); 3.9837 (6.2); 3.6360 (4.0); 3.5893 (3.3); 3.3440 (30.8); 2.8923 (3.4); 2.7326 (3.0); 2.6738 (0.4); 2.5135 (22.8); 2.5093 (44.0); 2.5048 (56.8); 2.5003 (41.6); 2.4961 (20.8); 2.3316 (0.4); 1.2401 (0.6); -0.0002 (1.4) 1.095: de1H NMR (400.2 MHz, d6-DMSO): δ= 8.9879 (7.5); 8.9754 (7.5); 8.7276 (1.3); 8.4148 (10.1); 8.3510 (14.5); 8.3297 (16.0); 7.9556 (0.5); 7.8941 (15.9); 7.8728 (14.6); 7.7943 (5.8); 7.7818 (5.5); 4.0406 (6.6); 3.9943 (8.2); 3.6487 (5.1); 3.6022 (4.1); 3.3467 (99.3); 2.8933 (3.0); 2.7340 (2.6); 2.6797 (0.4); 2.6752 (0.5); 2.6707 (0.3); 2.5148 (31.7); 2.5107 (60.6); 2.5062 (77.5); 2.5017 (55.6); 2.4975 (27.0); 2.3376 (0.3); 2.3332 (0.5); 2.3282 (0.3); 1.2361 (0.6); 0.0002 (1.5) I. 096: 1H NMR (400.2 MHz, d6-DMSO): δ= 10.2109 (9.7); 9.2671 (4.2); 9.2613 (4.2); 9.1057 (4.3); 9.1012 (4.3); 8.7452 (0.4); 8.6007 (2.7); 8.5954 (4.4); 8.5901 (2.5); 8.0520 (0.9); 8.0308 (1.1); 7.9933 (4.6); 7.9722 (7.2); 7.9526 (2.3); 7.8954 (7.1); 7.8743 (5.8); 7.8532 (1.1); 7.5504 (0.5); 7.5287 (0.5); 6.8440 (0.5); 6.8222 (0.5); 5.5734 (0.3); 4.0286 (2.5); 4.0202 (0.7); 3.9823 (3.0); 3.9734 (0.9); 3.6449 (2.0); 3.6279 (0.5); 3.5986 (1.6); 3.5782 (0.4); 3.3311 (170.5); 2.8906 (16.0); 2.7470 (0.9); 2.7309 (13.8); 2.6757 (1.0); 2.6711 (1.3); 2.6666 (1.0); 2.6191 (4.3); 2.5727 (0.4); 2.5560 (0.4); 2.5108 (86.9); 2.5066 (165.6); 2.5022 (210.9); 2.4977 (151.2); 2.4934 (74.0); 2.3334 (0.9); 2.3289 (1.2); 2.3246 (0.9); 1.3078 (1.3); 1.2580 (0.4); 1.2393 (1.7); 0.8530 (0.4); -0.0002 (4.6) Petition 870260051039, dated 05 / 28 / 2026, pp. 138 / 314 135 / 149 1.09 7: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.8532 (7.2); 8.8404 (7.5); 8.4453 (0.4); 8.2008 (9.4); 8.1985 (9.8); 8.0881 (5.5); 8.0842 (5.5); 8.0723 (16.0); 8.0512 (15.2); 7.9531 (1.1); 7.8982 (14.6); 7.8770 (12.0); 7.5473 (0.7); 7.5255 (0.8); 6.8416 (0.7); 6.8198 (0.7); 6.2964 (0.4); 4.6383 (0.3); 4.0238 (4.7); 3.9774 (5.9); 3.8104 (0.4); 3.6470 (4.5); 3.6004 (3.6); 3.4926 (0.4); 3.4467 (0.5); 3.3321 (56.5); 3.0924 (0.6); 3.0371 (0.4); 2.8910 (7.5); 2.7476 (0.8); 2.7311 (6.5); 2.6761 (1.0); 2.6716 (1.4); 2.6672 (1.0); 2.5732 (0.4); 2.5248 (4.7); 2.5115 (89.0); 2.5072 (172.2); 2.5027 (220.0); 2.4982 (157.2); 2.4938 (75.8); 2.3340 (1.0); 2.3295 (1.3); 2.3250 (0.9); 1.2392 (2.2); 1.1587 (0.4); 0.8528 (0.6); 0.0079 (0.4); -0.0002 (8.0) 1,098: RMN de1H (400.2 MHz, d6-DMSO): δ= 9.1705 (3.4); 9.1575 (3.6); 8.7487 (1.0); 8.6535 (4.7); 8.6324 (5.1); 8.5164 (2.8); 8.5033 (3.2); 8.2984 (1.9); 8.2854 (1.7); 8.2580 (3.4); 8.2449 (3.3); 8.1142 (3.7); 7.9562 (2.4); 7.9408 (5.3); 7.9196 (5.1); 7.8749 (0.4); 7.8473 (0.3); 4.0579 (2.1); 4.0117 (2.7); 3.6658 (1.7); 3.6197 (1.4); 3.3406 (25.0); 2.8938 (16.0); 2.7348 (13.6); 2.5287 (0.7); 2.5155 (13.0); 2.5112 (25.2); 2.5067 (32.2); 2.5021 (23.0); 2.4977 (11.2); -0.0002 (1.2) 1.099: de1H NMR (400.2 MHz, d6-DMSO): δ= 8.2887 (4.2); 7.9541 (1.9); 7.8231 (3.5); 7.8026 (4.1); 7.4760 (3.4); 7.4557 (3.1); 7.3032 (4.5); 4.0181 (1.6); 3.9805 (16.0); 3.9721 (2.5); 3.6257 (1.4); 3.5790 (1.2); 3.3420 (12.6); 2.8924 (12.2); 2.7329 (11.1); 2.5090 (17.8); 2.5047 (22.6); 2.5004 (16.6); 1.3086 (0.7); -0.0002 (0.4) I.100: de1H NMR (400.2 MHz, d6-DMSO): δ= 8.7212 (0.8); 8.2711 (2.7); 8.2577 (2.8); 7.9288 (3.2); 7.9076 (5.5); 7.8517 (5.5); 7.8306 (3.2); 7.3887 (1.9); 7.3850 (2.0); 7.3752 (1.8); 7.3715 (1.9); 7.1898 (3.5); 7.1878 (3.5); 4.0153 (1.9); 3.9689 (2.4); 3.9080 (16.0); 3.6291 (1.6); 3.5825 (1.3); 3.3372 (17.3); 2.8916 (1.8); 2.7327 (1.6); 2.5084 (20.2); 2.5040 (25.6); 2.4997 (18.8); -0.0002 (0.8) Petition 870260051039, dated 05 / 28 / 2026, pp. 139 / 314 136 / 149 1.101: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.9438 (5.0); 8.9337 (5.1); 8.7135 (1.8); 8.3589 (5.0); 8.3557 (4.9); 8.3388 (5.4); 8.3355 (5.1); 7.8545 (13.4); 7.8378 (6.2); 7.8337 (16.0); 7.7183 (3.4); 7.7062 (3.5); 7.6993 (3.4); 7.6872 (3.2); 7.5846 (12.5); 7.5640 (10.8); 4.0431 (6.0); 3.9967 (7.5); 3.6388 (4.7); 3.5923 (3.8); 3.3332 (27.6); 2.8917 (1.2); 2.7324 (1.1); 2.6772 (0.4); 2.6726 (0.6); 2.6681 (0.4); 2.5256 (2.0); 2.5125 (39.8); 2.5082 (76.5); 2.5037 (97.5); 2.4991 (69.4); 2.4947 (33.4); 2.3349 (0.4); 2.3304 (0.6); 2.3259 (0.4); 1.2399 (0.8); 0.0001 (4.0) 1.102: RMN de1H (400.2 MHz, d6-DMSO): δ = 8.7004 (0.6); 8.1405 (6.6); 8.0091 (7.0); 7.9955 (7.2); 7.9550 (2.2); 7.8494 (9.1); 7.8283 (16.0); 7.7749 (15.5); 7.7537 (8.9); 6.8723 (5.1); 6.8687 (5.2); 6.8587 (5.0); 6.8550 (5.1); 6.7889 (9.3); 6.1741 (4.8); 4.0085 (5.6); 3.9622 (7.0); 3.6218 (4.8); 3.5754 (3.9); 3.4472 (0.3); 2.8916 (13.8); 2.7329 (12.3); 2.6740 (0.3); 2.5096 (43.2); 2.5052 (55.1); 2.5007 (40.5); 2.3322 (0.4); 1.1599 (0.6); -0.0002 (8.6); -0.0085 (0.4) 1.103: RMN de1H (400.2 MHz, d6-DMSO): δ = 8.6934 (1.7); 8.5035 (1.7); 8.4998 (1.9); 8.4916 (1.9); 8.4878 (1.8); 7.8331 (4.1); 7.8124 (4.7); 7.6585 (1.6); 7.6548 (1.6); 7.6394 (1.8); 7.6357 (1.8); 7.5420 (4.7); 7.5214 (4.2); 7.3488 (1.4); 7.3367 (1.4); 7.3297 (1.4); 7.3177 (1.2); 4.0213 (1.9); 3.9749 (2.4); 3.6345 (1.6); 3.5880 (1.2); 3.3399 (6.4); 2.8918 (0.9); 2.7323 (0.8); 2.5086 (15.6); 2.5043 (20.1); 2.4998 (15.0); 2.4460 (16.0); -0.0002 (2.9) I.104: 1H NMR (300.2 MHz, d6-DMSO): δ= 9.0665 (7.7); 8.7133 (1.0); 7.9289 (1.1); 7.9001 (3.0); 7.8653 (2.8); 7.8366 (1.1); 7.5276 (0.8); 7.5220 (1.0); 7.5001 (1.7); 7.4592 (0.6); 7.4533 (0.8); 7.4471 (0.4); 7.4309 (1.9); 7.4258 (0.8); 7.4112 (0.6); 7.4066 (1.1); 7.3975 (0.6); 7.3918 (0.9); 7.3865 (0.5); 7.3688 (0.7); 5.4927 (4.4); 4.0356 (0.8); 3.9736 (1.0); 3.6521 (0.7); 3.5905 (0.5); 3.3440 (16.0); 2.5343 (4.7); 2.5283 (9.8); 2.5222 (13.5); 2.5162 (9.8); 2.5102 (4.6); 0.0315 (0.4); 0.0206 (12.2); 0.0096 (0.5) Petition 870260051039, dated 05 / 28 / 2026, page 140 / 314 137 / 149 1.105: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.7202 (12.0); 8.5967 (4.9); 8.5933 (4.1); 8.5900 (4.2); 8.5855 (5.0); 8.0548 (8.8); 8.0368 (10.9); 8.0341 (9.8); 7.9568 (0.5); 7.9102 (3.0); 7.9080 (3.1); 7.8930 (16.0); 7.8719 (12.2); 7.8602 (3.5); 7.8580 (3.3); 7.5598 (2.7); 7.5493 (4.4); 7.5389 (4.8); 7.5283 (3.7); 7.5180 (2.2); 4.0286 (5.8); 3.9823 (7.2); 3.6401 (4.6); 3.5933 (3.7); 3.3461 (27.2); 2.8935 (2.8); 2.7346 (2.5); 2.5115 (34.0); 2.5071 (43.4); 2.5027 (31.9); -0.0002 ϊ^6________________________________________________________ 1.106: RMN de1H (400.2 MHz, d6-DMSO): δ= 9.1166 (3.2); 9.1037 (3.3); 8.7150 (1.0); 7.9535 (2.0); 7.8925 (4.1); 7.8717 (5.7); 7.7601 (5.8); 7.7393 (4.3); 7.6865 (2.4); 7.6732 (2.4); 7.5540 (1.0); 7.5323 (1.1); 6.8470 (1.0); 6.8253 (1.0); 4.0502 (2.1); 4.0038 (2.6); 3.8656 (0.4); 3.8200 (0.6); 3.6575 (1.7); 3.6107 (1.4); 3.4951 (0.4); 3.3351 (19.4); 2.8911 (12.6); 2.7316 (11.1); 2.5076 (35.0); 2.5031 (44.5); 2.4987 (32.5); 2.3489 (16.0); 2.3300 (0.4); 1.3093 (0.8); -0.0002 (5.1) 1,107: RMN de1H (400.2 MHz, d6-DMSO): δ= 9.0753 (3.0); 9.0700 (3.1); 8.8954 (3.2); 8.8900 (3.1); 8.7594 (2.5); 8.2749 (0.6); 8.1049 (0.4); 8.0732 (3.9); 8.0522 (5.9); 7.9760 (5.7); 7.9548 (6.4); 7.9399 (1.0); 4.0614 (2.1); 4.0149 (2.6); 3.6712 (1.7); 3.6248 (1.4); 3.3427 (20.4); 2.8924 (16.0); 2.7329 (14.9); 2.5092 (22.2); 2.5048 (27.9); 2.5005 (20.7); 1.3223 (0.6); 1.1653 (0.5); 1.1540 (0.7); 1.1315 (0.4); 1.1202 (0.6); -0.0002 (3.8) I.108: 1H NMR (400.2 MHz, d6-DMSO): δ= 9.2795 (2.8); 9.2672 (2.9); 8.7496 (3.4); 8.4805 (3.9); 8.4591 (4.3); 8.1245 (2.8); 8.1122 (2.7); 7.9548 (2.7); 7.9438 (4.1); 7.9224 (3.8); 4.0481 (1.6); 4.0018 (2.0); 3.6463 (1.3); 3.5997 (1.1); 3.3422 (13.9); 2.8933 (16.0); 2.7342 (14.2); 2.7333 (14.0); 2.5279 (0.4); 2.5144 (7.9); 2.5102 (15.2); 2.5057 (19.3); 2.5012 (14.1); 2.4969 (7.0); -0.0002 (3.0) Petition 870260051039, dated 05 / 28 / 2026, page 141 / 314 138 / 149 1.109: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.7349 (2.6); 8.6596 (3.0); 8.6453 (3.1); 8.4986 (3.6); 8.4773 (4.0); 7.8937 (3.8); 7.8724 (3.6); 6.9352 (3.1); 6.9208 (3.0); 4.0646 (16.0); 4.0310 (1.5); 3.9848 (1.9); 3.6434 (1.2); 3.5968 (1.0); 3.3620 (31.9); 2.5170 (5.3); 2.5128 (10.2); 2.5083 (13.2); 2.5038 (9.6); 2.4995 (4.8); -0.0002 (0.4) 1.110: de1H NMR (400.2 MHz, d6-DMSO): δ= 8.7119 (3.4); 8.3726 (2.7); 8.3661 (3.0); 8.2728 (2.9); 8.2663 (2.6); 8.1490 (3.4); 8.1277 (4.0); 7.8535 (3.7); 7.8323 (3.2); 4.0127 (16.0); 3.9704 (1.9); 3.6339 (1.2); 3.5871 (1.0); 3.3406 (5.9); 2.8928 (0.9); 2.7338 (0.8); 2.5104 (10.8); 2.5060 (13.8); 2.5015 (10.2); -0.0002 (2.0) 1.111: de 1 H NMR (500.1 MHz, CDCl 3 ): δ= 8.7266 (4.3); 8.7165 (4.3); 7.9727 (7.0); 7.9562 (7.6); 7.7216 (5.9); 7.6642 (7.6); 7.6477 (6.8); 7.3158 (3.2); 7.3063 (3.2); 7.2616 (4.8); 5.2977 (5.7); 3.8653 (16.0); 3.6924 (3.4); 3.6571 (4.5); 3.4458 (3.1); 3.4104 (2.4); 2.9491 (0.5); 2.8581 (0.5); 1.3280 (0.4); 1.2561 (6.3); 1.2419 (1.5); 1.2278 (0.9); 0.8934 (0.7); 0.8804 (1.2); 0.8667 (1.0); 0.8596 (1.2); 0.8466 (1.4); -0.0002 (4.9) 1.112: RMN de1H (400.2 MHz, d6-DMSO): δ= 9.3551 (8.0); 8.7659 (6.2); 8.7226 (9.4); 8.6731 (7.0); 8.6673 (6.4); 8.2886 (9.2); 8.2676 (10.3); 7.9567 (2.7); 7.9071 (10.2); 7.8861 (9.4); 4.0380 (4.5); 3.9916 (5.6); 3.6500 (3.8); 3.6035 (3.0); 3.3441 (19.9); 2.8937 (16.0); 2.7346 (14.9); 2.5113 (31.6); 2.5071 (39.8); 2.5028 (29.8); -0.0002 (5.6) I.113: RMN de1H (400.2 MHz, d6-DMSO): δ = 8.9625 (15.9); 8.9504 (16.0); 8.7263 (7.9); 8.6462 (0.4); 8.5030 (10.9); 8.4819 (11.8); 7.9568 (1.7); 7.9073 (11.2); 7.8861 (10.5); 7.7379 (0.7); 7.7225 (0.7); 7.7181 (0.8); 7.5191 (4.1); 7.5069 (8.6); 7.4949 (4.0); 4.0356 (4.8); 3.9892 (6.0); 3.9698 (0.6); 3.9231 (0.6); 3.6411 (3.9); 3.5946 (3.1); 3.5364 (0.3); 3.3486 (42.0); 2.8936 (10.3); 2.7348 (9.4); 2.5117 (34.7); 2.5073 (44.3); 2.5029 (32.9); -0.0002 (4.3) Petition 870260051039, dated 05 / 28 / 2026, page 142 / 314 139 / 149 1.114: 1Η NMR (400.2 MHz, d6-DMSO): δ= 8.2636 (4.1); 8.2425 (4.6); 8.2232 (2.4); 8.2013 (2.6); 7.9003 (4.5); 7.8792 (4.1); 7.7052 (2.8); 7.6832 (2.6); 4.0129 (1.5); 3.9667 (1.9); 3.6423 (1.6); 3.5960 (1.3); 3.3581 (5.0); 2.8924 (1.2); 2.7329 (1.1); 2.6820 (16.0); 2.5278 (0.6); 2.5143 (10.8); 2.5101 (21.2); 2.5056 (27.3); 2.5011 (19.9); 2.4968 (10.0); -0.0002 (3.5) I.115: 1H NMR (400.1 MHz, d6-DMSO): δ= 8.7498 (6.6); 8.4041 (8.4); 8.3108 (4.2); 8.2869 (1.4); 8.2793 (1.1); 8.2670 (2.5); 8.2602 (2.0); 8.2470 (1.4); 8.2396 (1.0); 7.9158 (8.7); 7.8950 (16.0); 7.8848 (6.7); 7.8638 (9.6); 7.8463 (12.0); 7.8265 (7.1); 7.8023 (7.0); 7.7828 (4.4); 7.5889 (4.5); 7.5838 (4.7); 7.5764 (4.7); 7.5716 (4.1); 4.0356 (5.6); 4.0268 (3.8); 3.9890 (7.1); 3.9802 (4.7); 3.6448 (5.8); 3.5992 (4.6); 3.3360 (48.3); 2.5077 (42.1); 1.9945 (0.7); 1.2386 (1.1); 1.1793 (0.4); 0.8771 (0.4); 0.8630 (0.9); 0.8465 (0.4) BIOLOGICAL DATA Example: preventive in vivo test in Puccinia recondita (brown rust in wheat) Solvent: 5% by volume of dimethyl sulfoxide, 5% by volume of acetone. Emulsifier: 1 μL of Tween® 80 per mg of active ingredient
[0230] The active ingredients were soluble and homogenized in a mixture of Dimethyl Sulfoxide / Acetone / / Tween® 80 and then diluted in water to the desired concentration.
[0231] 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. Petition 870260051039, dated 05 / 28 / 2026, pp. 143 / 314 140 / 149
[0232] 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.
[0233] 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.
[0234] 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.026; I.027; I.029; I.042; I.046; I.066; I.107; I.108
[0235] In this test, the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 250 ppm of active ingredient: I.008; I.011; I.014; I.020; I.030; I.039; I.043; I.048; I.049; I.050; I.056; I.057; I.059; I.060; I.061; I.062; I.069; I.103; I.115
[0236] 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.002; I.005; I.006; I.009; I.012; I.016; I.019; I.021; I.022; I.023; I.024; I.025; I.028; I.032; I.037; I.052; I.053; I.054; I.055; I.063; I.067; I.105; I.112; I.113 Example: preventive in vivo test on Phakospora pachyrhizi (soybean rust) Solvent: 5% by volume of dimethyl sulfoxide, 5% by volume of acetone. Emulsifier: 1 μL of Tween® 80 per mg of active ingredient Petition 870260051039, dated 05 / 28 / 2026, pp. 144 / 314 141 / 149
[0237] The active ingredients were soluble and homogenized in a mixture of Dimethyl Sulfoxide / Acetone / / Tween® 80 and then diluted in water to the desired concentration.
[0238] 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.
[0239] 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% relative humidity and then for 10 days at 24 °C and 70–80% relative humidity.
[0240] 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.
[0241] 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.044; I.074
[0242] 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.028; I.045; I.046; I.056; I.107; I.109; I.110; I.111
[0243] 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; I.002; I.003; I.005; I.008; I.009; I.010; I.011; I.012; I.016; I.019; I.021; I.023; I.024; I.025; I.029; I.030; I.032; I.036; I.037; I.038; I.039; I.042; I.049; I.050; I.052; I.053; I.054; I.055; I.057; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.069; I.071; I.072; I.073; I.105; I.108; I.112; I.113; I.115. Petition 870260051039, dated 05 / 28 / 2026, page 145 / 314 142 / 149 Example: Pythium ultimum in vitro cell test Solvent: DMSO 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), 1 liter of QSP Inoculum: mycelial suspension
[0244] 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%.
[0245] The inoculum was prepared from a pre-culture of P. ultimum grown in liquid medium by homogenization in a blender. The concentration of ground mycelium in the inoculum was estimated and adjusted for the desired optical density (OD).
[0246] The 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 4 days of incubation, the fungicidal efficacy of the compounds was determined by spectrometric measurement of mycelial growth. The inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
[0247] 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.004; I.008; I.014; I.016; I.025; I.028; I.101; I.115
[0248] 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.029; I.032; I.066; I.079 Petition 870260051039, dated 05 / 28 / 2026, pp. 146 / 314 143 / 149
[0249] 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.003; I.005; I.006; I.009; I.013; I.015; I.017; I.018; I.022; I.027; I.030; I.034; I.036; I.037; I.038; I.039; I.040; I.041; I.049; I.071; I.072; I.073; I.080; I.081; I.082; I.085; I.093; I.095; I.099; I.100 Example: Piricularia oryzae in vitro cell test Solvent: DMSO 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), 1 liter of QSP Inoculum: spore suspension
[0250] 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%.
[0251] A suspension of P. oryzae spores was prepared and diluted to the desired spore density.
[0252] 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 toxicity of the compounds to fungi was determined by spectrometric measurement of mycelial growth. The inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.
[0253] 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.008; I.010; I.021; I.030; I.033; I.042; I.057; I.088; I.107; I.108 Petition 870260051039, dated 05 / 28 / 2026, page 147 / 314 144 / 149
[0254] 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.014; I.018; I.025; I.032; I.053; I.055; I.058; I.081; I.095; I.098
[0255] 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.003; I.005; I.006; I.009; I.011; I.013; I.016; I.017; I.022; I.023; I.026; I.027; I.029; I.034; I.035; I.036; I.038; I.039; I.040; I.043; I.047; I.049; I.071; I.072; I.073; I.075; I.076; I.079; I.080; I.082; I.085; I.086; I.087; I.091; I.092; I.093; I.099; I.100; I.101; I.110; I.115 Example: in vitro cell test of Rhizoctonia solani Solvent: DMSO 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), 1 liter of QSP Inoculum: mycelial suspension
[0256] 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%.
[0257] The inoculum was prepared from a preculture of R. solani grown in liquid medium by homogenization using a blender. The concentration of ground mycelium in the inoculum was estimated and adjusted to the desired optical density (OD).
[0258] The 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. The inhibition of fungal growth was determined by comparing the absorbance values in Petition 870260051039, dated 05 / 28 / 2026, page 148 / 314 145 / 149 wells containing fungicides with absorbance in control wells without fungicides.
[0259] 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.010; I.022; I.032; I.055; I.086; I.091
[0260] 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.008; I.029; I.037; I.038; I.071; I.093; I.115
[0261] In this test, the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 20 ppm of active ingredient: I.003; I.005; I.006; I.009; I.011; I.013; I.016; I.017; I.020; I.026; I.027; I.034; I.035; I.036; I.039; I.040; I.043; I.049; I.072; I.073; I.076; I.080; I.082; I.085; I.087; I.092; I.095; I.099 Example: in vitro cell test of Colletotrichum lindemuthianum Solvent: DMSO Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g mycological peptone (Oxoide), 1.4 g granulated yeast extract (Merck), 1 liter q.s.p. Inoculum: spore suspension
[0262] 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%.
[0263] A spore suspension of C. lindemuthianum was prepared and diluted to the desired spore density.
[0264] 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 toxicity of the compounds to fungi was Petition 870260051039, dated 05 / 28 / 2026, page 149 / 314 146 / 149 determined by spectrometric measurement of mycelial growth. Inhibition of fungal growth was determined by comparing absorbance values in wells containing fungicides with absorbance in control wells without fungicides.
[0265] In this test, the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 20 ppm of active ingredient: I.015; I.044; I.053; I.078; I.102; I.109
[0266] 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.010; I.019; I.024; I.026; I.027; I.032; I.042; I.050; I.056; I.059; I.060; I.061; I.062; I.064; I.065; I.066; I.069; I.088; I.089; I.098; I.103; I.106; I.107; I.110; I.114
[0267] 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.003; I.005; I.006; I.008; I.009; I.011; I.012; I.013; I.014; I.016; I.017; I.018; I.020; I.021; I.022; I.023; I.025; I.029; I.030; I.033; I.034; I.035; I.036; I.037; I.038; I.039; I.040; I.043; I.045; I.046; I.047; I.049; I.052; I.054; I.055; I.057; I.058; I.063; I.067; I.071; I.072; I.073; I.075; I.076; I.079; I.080; I.081; I.082; I.085; I.086; I.087; I.091; I.092; I.093; I.094; I.095; I.099; I.100; I.101; I.104; I.111; I.112; I.113; I.115 Example: preventive in vivo test in the 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
[0268] To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the established quantities of Petition 870260051039, dated 05 / 28 / 2026, pp. 150 / 314 147 / 149 solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.
[0269] To test preventive activity, young plants were sprayed with the active compound preparation at the established 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 humidity of 95 .
[0270] The plants remained in the incubation chamber at approximately 24 °C and a relative air humidity of approximately 80 % and a day / night interval of 12 h.
[0271] 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 the 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
[0272] To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the established quantities of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.
[0273] 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 humidity of 95 . Petition 870260051039, dated 05 / 28 / 2026, pp. 151 / 314 148 / 149
[0274] The plants remained in the incubation chamber at approximately 24 °C and a relative air humidity of approximately 80 % and a day / night interval of 12 h.
[0275] Two days after inoculation, the plants were sprayed with the active compound preparation at the established application rate and remained, in addition, in the incubation chamber.
[0276] 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: long-duration in vivo activity test in the 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
[0277] To produce a suitable preparation of the active compound, 1 part by weight of the active compound was mixed with the established quantities of solvent and emulsifier, and the concentrate was diluted with water to the desired concentration.
[0278] To test long-term activity, young plants were sprayed with the active compound preparation at the established application rate. After the spray coating dried, the plants were placed in an incubation chamber at approximately 24 °C and a relative humidity of approximately 80% and a day / night interval of 12 h.
[0279] 8 days after application, the plants were inoculated with an aqueous spore suspension 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 humidity of 95 . Petition 870260051039, dated 05 / 28 / 2026, page 152 / 314 149 / 149
[0280] The plants remained in the incubation chamber at approximately 24 °C and a relative air humidity of approximately 80 % and a day / night interval of 12 h.
[0281] The test was evaluated 7 days after inoculation. 0% means an efficacy that corresponds to that of the untreated control, while an efficacy of 100% means that no disease was observed.
Claims
CLAIMS 1. Compound CHARACTERIZED in that it is of formula (I): Het (R2)n wherein: R1 is hydrogen, X is a fluorine or chlorine atom; m is 0 or 1; Het is pyridinyl, pyridazinyl, pyrimidinyl or pyrazinyl; n is 1 or 2; R2 is a substituent independently selected from the group consisting of chlorine, bromine, cyano, amino, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-hydroxyalkyl, C1-C6-cyanoalkyl, C2-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, di-C1-C6-alkylamino, C2-C6-alkynyl, C1-C6-alkylsulfanyl, phenyl, pyridinyl, phenoxy, formyl, benzylamino and benzyloxy, wherein the phenyl, pyridinyl and phenoxy radicals R2 may be substituted by a fluorine atom, or a salt or N-oxide thereof.
2. Compound of formula (I), according to claim 1, CHARACTERIZED in that X is a fluorine atom.
3. Composition CHARACTERIZED in that it comprises at least one compound of formula (I), as defined in claim 1 or 2, and at least one agriculturally acceptable carrier. Petition 870260051039, dated 05 / 28 / 2026, pp. 308 / 314 2 / 2 4. Use of a compound of formula (I), as defined in claim 1 or 2, or of a composition, as defined in claim 3, CHARACTERIZED in that it is for the control of phytopathogenic fungi in plants.
5. Method for controlling phytopathogenic fungi CHARACTERIZED in that it comprises the step of applying at least one compound of formula (I), as defined in claim 1 or 2, or a composition, as defined in claim 3, to plants, plant parts, seeds, fruits or the soil in which the plants grow.