FUSED PYRROLIDINE-2-ONE HERBICIDE COMPOUNDS

Description

FUSED PYRROLIDINE-2-ONE HERBICIDE COMPOUNDS

[0001] The present invention relates to innovative herbicidal compounds, to processes for their preparation, to herbicidal compositions comprising the innovative compounds and to their use for controlling weeds, particularly in useful plant crops, or for inhibiting plant growth.

[0002] Pyrrolidine-2-one herbicides are known from EP-A-0004107, US 5,352,655 and WO2022 / 200208. Thus, according to the present invention, a compound of Formula (I) is provided. in what X = -(CR2R3)m-; Y = O or S; Q is phenyl optionally substituted by 1 to 4 R4 substituents. R1 is hydrogen or C1-C6 alkyl R2e R3 are independently selected from the group consisting of hydrogen, methyl, fluorine and chlorine; R4 halogen, cyano, C1-C6-alkyl, C1-C6-alkoxy-, C1-C6-haloalkyl, C1-C6-haloalkoxy- and -S(O)pC1-C6alkyl; m = 1, 2, 3 or 4; n = 1 or 2; ep = 0, 1 or 2.

[0003] C1-Cealkyl- includes, for example, methyl (Me, CH3), ethyl (Et, C2H5), n-propyl (n-Pr), isopropyl (i-Pr), Petition 870250089696, dated 02 / 10 / 2025, p. 16 / 73 2 / 55 n-butyl (n-Bu), isobutyl (i-Bu), sec-butyl and tert-butyl (t-Bu). Ci-C2alkyl is methyl (Me, CH3) or ethyl (Et, C2H5).

[0004] Halogen (or halo) includes, for example, fluorine, chlorine, bromine, or iodine. The same applies correspondingly to halogen in the context of other definitions, such as haloalkyl.

[0005] C1-C6haloalkyl- includes, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro2,2,2-trichloroethyl, 2,2,3,3-tetrafluoropropyl and 2,2,2trichloroethyl and heptafluoro-n-propyl. C1-C2haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl or 1,1-difluoro-2,2,2-trichloroethyl.

[0006] C1-C6 alkoxy includes methoxy and ethoxy.

[0007] C1-C4haloalkoxy- includes, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy or 2,2,2-trichloroethoxy, preferably difluoromethoxy, 2-chloroethoxy or trifluoromethoxy.

[0008] C1-C6alkyl-S- (alkylthio) includes, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio.

[0009] C1-C6alkyl-S(O)- (alkylsulfinyl) includes, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, Petition 870250089696, dated 02 / 10 / 2025, p. 17 / 73 3 / 55 sec-butylsulfinyl or tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.

[0010] C1-C6alkyl-S(O)2- (alkylsulfonyl) includes, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

[0011] In one embodiment of the present invention Y is S. In a preferred embodiment of the present invention Y is O.

[0012] In a preferred embodiment of the present invention, X is -(CR2R3)-. In a more preferred embodiment of the present invention, X is -(CH2)-.

[0013] In one embodiment of the present invention, Q is unsubstituted phenyl. In a preferred embodiment of the present invention, Q is substituted by one, two or three (preferably two or three) R4. In a more preferred embodiment of the present invention, Q is 2,3-difluorophenyl, 2,3,4-trifluorophenyl or 2,3,5-trifluorophenyl.

[0014] In a preferred embodiment of the present invention, R1 is hydrogen or methyl.

[0015] The compounds of Formula (I) may contain asymmetric centers and may be present as a single enantiomer, pairs of enantiomers in any proportion, or, where more than one asymmetric center is present, contain diastereomers in all possible ratios. Typically, one of the stereoisomers has enhanced biological activity compared to the other possibilities. For example, in the context of the present invention, the compounds of Formula (I) in which X is CH2 may exist in the following alternative forms, wherein the relative stereochemistry between Petition 870250089696, dated 02 / 10 / 2025, p. 18 / 73 4 / 55 C (1) and C (2) may alternatively be cis- or trans-, and each diastereoisomer is further comprised of a pair of individual enantiomers with opposite absolute configuration, for example, the enantiomeric pair (1a) (1R,2R,5S) and (1b) (1S,2S,5R), and the enantiomeric pair (1c) (1R,2S,5S) and (1d) (1S,2R,5R): (W) Q. X(CH2)n I (Ib) C) kCH2)n I (d)

[0016] The expert is aware of methods recognized in the art for separating the various stereoisomers of compounds of Formula (I).

[0017] The present invention also provides agronomically acceptable salts of compounds of Formula (I). Of the salts that the compounds of Formula (I) can form with amines, including primary, secondary and tertiary amines (for example ammonia, dimethylamine and triethylamine), alkali metal and alkaline earth metal bases, transition metal bases or quaternary ammonium bases are preferred.

[0018] The compounds of Formula (I) according to the invention can be used as herbicides on their own, but are generally formulated into herbicidal compositions using formulation adjuvants such as carriers, solvents and surfactants (SAAs). Thus, the present invention further provides a herbicidal composition. Petition 870250089696, dated 02 / 10 / 2025, page 19 / 73 5 / 55 comprising a herbicidal compound according to any of the preceding claims and an agriculturally acceptable formulation adjuvant. The composition may be in the form of concentrates that are diluted before use, although ready-to-use compositions may also be prepared. The final dilution is usually made with water, but may be made instead of, or in addition to, water, with, for example, liquid fertilizers, micronutrients, biological organisms, oil or solvents.

[0019] Herbicidal compositions generally comprise 0.1 to 99% by weight, especially 0.1 to 95% by weight, of the compounds of Formula I and 1 to 99.9% by weight of a formulation adjuvant that preferably includes 0 to 25% by weight of a surfactant.

[0020] Compositions may be chosen from a number of formulation types. These include an emulsified concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG), a water-in-oil emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a soluble powder (SP), a wettable powder (WP), and a soluble granule (SG). The formulation type chosen in any case will depend on the particular intended purpose and the physical, chemical, and biological properties of the Formula (I) compound. Petition 870250089696, dated 02 / 10 / 2025, page 20 / 73 6 / 55

[0021] Soluble powders (SP) can be prepared by mixing a compound of Formula (I) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or magnesium sulfate) or one or more water-soluble organic solids (such as a polysaccharide) and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve dispersibility / solubility in water. The mixture is then ground to a fine powder. Similar compositions can also be granulated to form water-soluble granules (GS).

[0022] Wettable powders (WP) can be prepared by mixing a compound of Formula (I) with one or more solid diluents or carriers, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions can also be granulated to form water-dispersible granules (WG).

[0023] The granules (GR) may be formed by granulating a mixture of a compound of Formula (I) and one or more solid powder diluents or carriers or from pre-formed empty granules by absorption of a compound of Formula (I) (or a solution thereof in a suitable agent) onto a porous granular material (such as pumice, attapulgite clays, Fuller's earth, kieselguhr, diatomaceous earth or crushed corn cobs) or by adsorption of a compound of Formula (I) (or a solution thereof in a suitable agent) onto a hard core material (such as Petition 870250089696, dated 02 / 10 / 2025, p. 21 / 73 7 / 55 sands, silicates, carbonates, sulfates or mineral phosphates) and drying if necessary. Agents that are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and adhesive agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).

[0024] Dispersible concentrates (DCs) can be prepared by dissolving a compound of Formula (I) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surfactant (e.g. to improve dilution in water or to prevent crystallization in a spray tank).

[0025] Emulsifiable concentrates (ECs) or oil-in-water emulsions (EWs) can be prepared by dissolving a compound of Formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents, or a mixture of said agents). Suitable organic solvents for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150, and SOLVESSO 200; SOLVESSO is a Registered Trademark), ketones (such as cyclohexanone or methylcyclohexanone), and alcohols (such as benzyl alcohol, furfuryl alcohol, or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), fatty acid dimethylamides (such as dimethylamide of Petition 870250089696, dated 02 / 10 / 2025, p. 22 / 73 8 / 55 C8-C10 fatty acids) and chlorinated hydrocarbons. An EC product can emulsify spontaneously upon addition to water, to produce an emulsion with sufficient stability to allow application by spraying using appropriate equipment.

[0026] The preparation of an EW involves obtaining a compound of Formula (I) either as a liquid (if not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in a suitable solvent) and then emulsifying the resulting liquid or solution in water containing one or more SAAs, under high shear, to produce an emulsion. Suitable solvents for use in EW include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other suitable organic solvents that have low solubility in water.

[0027] Microemulsions (MEs) can be prepared by mixing water with a mixture of one or more solvents with one or more SAAs to spontaneously produce a thermodynamically stable isotropic liquid formulation. A compound of Formula (I) is initially present in the water or in the solvent / SAA mixture. Suitable solvents for use in MEs include those previously described for use in ECs or EWs. An ME can be an oil-in-water or water-in-oil system (which system is present can be determined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. An ME is suitable for dilution in water, Petition 870250089696, dated 02 / 10 / 2025, page 23 / 73 9 / 55 both remaining as a microemulsion and forming a conventional oil-in-water emulsion.

[0028] Suspension concentrates (SCs) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of Formula (I). SCs may be prepared by ball or spherule grinding of the solid compound of Formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a suspension of fine particles of the compound. One or more wetting agents may be included in the composition and a suspending agent may be included to reduce the rate at which the particles settle. Alternatively, a compound of Formula (I) may be dry-ground and added to water, containing previously described agents, to produce the desired end product.

[0029] The aerosol formulations comprise a compound of Formula (I) and a suitable propellant (e.g. n-butane). A compound of Formula (I) may also be dissolved or dispersed in a suitable medium (e.g. water or a water-miscible liquid such as n-propanol) to provide compositions for use in non-pressurized, hand-held spray pumps.

[0030] Capsule suspensions (CS) can be prepared in a similar manner to the preparation of EW formulations, but with an additional polymerization step, such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of Formula (I) and, optionally, a carrier or diluent thereof. The polymeric shell can be produced either by a reaction Petition 870250089696, dated 02 / 10 / 2025, page 24 / 73 10 / 55 interfacial polycondensation as well as by a coacervation procedure. The compositions can provide controlled release of the compound of Formula (I) and can be used for seed treatment. A compound of Formula (I) can also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.

[0031] The composition may include one or more additives to improve the biological performance of the composition, for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or absorption or mobility of a compound of Formula (I). Such additives include surfactants (SAAs), oil-based spray additives, for example certain mineral oils or natural vegetable oils (such as soybean and rapeseed oil), modified vegetable oils such as methylated rapeseed oil (MRSO) and mixtures thereof with other bio-enhancing adjuvants (ingredients that may assist or modify the action of a compound of Formula (I).

[0032] Wetting agents, dispersing agents and emulsifying agents can be cationic, anionic, amphoteric or non-ionic SAAs.

[0033] Suitable cationic type SAAs include quaternary ammonium compounds (e.g., cetyltrimethylammonium bromide), imidazolines, and amine salts.

[0034] Suitable anionic SAAs include alkali metal salts of fatty acids, salts of aliphatic sulfuric acid monoesters (e.g. sodium lauryl sulfate), salts of sulfonated aromatic compounds (e.g. sodium dodecylbenzenesulfonate, dodecylbenzenesulfonate) Petition 870250089696, dated 02 / 10 / 2025, page 25 / 73 11 / 55 of calcium, butylnaphthalenesulfonate and mixtures of sodium diisopropyl- and triisopropyl-naphthalenesulfonates), ether sulfates, alcohol ether sulfates (e.g. sodium laureth-3-sulfate), ether carboxylates (e.g. sodium laureth-3-carboxylate), phosphate esters (products of the reaction between one or more fatty alcohols and phosphoric acid (predominantly monoesters) or phosphorus pentoxide (predominantly diesters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally, these products may be ethoxylated), sulfosuccinates, paraffin or olefin sulfonates, taurates, lignosulfonates and triestyrylphenol phosphates / sulfates.

[0035] Suitable amphoteric-type SAAs include betaines, propionates, and glycinates.

[0036] Suitable non-ionic SAAs include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long-chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (e.g., polyethylene glycol esters of fatty acids); amine oxides (e.g., lauryl dimethylamine oxide); lecithins and sorbitans and their esters, alkyl polyglycosides and tristeylphenols.

[0037] Suitable suspending agents include hydrophilic colloids (such as polysaccharides, Petition 870250089696, dated 02 / 10 / 2025, p. 26 / 73 12 / 55 polyvinylpyrrolidone or sodium carboxymethylcellulose) and expandable clays (such as bentonite or attapulgite).

[0038] The compounds of the present invention can also be used in mixture with one or more additional herbicides and / or plant growth regulators. Examples of such additional herbicides or plant growth regulators include acetochlor, acifluorfen (including acifluorfen-sodium), aclonifene, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamide-M, benquitrione, bensulfurone (including bensulfurone-methyl), bentazone, bicyclopyrone, bilanafos, bipyrazone, bispiribacosodium, bixlozone, broclozone, bromacil, bromoxynil, butachlor, butafenacil, carfentrazone (including carfentrazone-ethyl), cloransulam (including cloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotolurone, chlorsulfuron, cinmethylin, clacifos, clethodim, clodinafop (including clodinafop-propargyl), clomazone, clopiralide, cyclopyranil, cyclopyrimorate, cyclosulfamurone, cyalafop (including cyalafop-butyl), 2,4-D (including choline salt and 2-ethylhexyl ester thereof), 2,4-DB, desmedifam, dicamba (including the aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts thereof), diclosulam, diflufenican, diflufenzopyr, dimetachlor, dimethenamide-P, dioxopyritrione, diquat dibromide, diurone, epirifenacil, etalfluralin, etofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenpyrazone, phenquinotrione, fentrazamide, flazasulfurone, florasulam, florpyrauxifene (including florpyrauxifene, Petition 870250089696, dated 02 / 10 / 2025, page 27 / 73 13 / 55 benzyl), fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), fluchloraminopyr (including fluchloramino-tefuryl), flufenacet, flufenoximacyl, flumetsulam, flumioxazin, fluometurone, fomesafen, flupyrsulfurone (including flupyrsulfuron-methyl-sodium), fluroxypyr (including fluroxypyr-meptyl), flusulfinam, fomesafen, foramsulfuron, glufosinate (including L-glufosinate and the ammonium salts of both), glyphosate (including the diammonium, isopropylammonium and potassium salts), halauxifene (including halauxifene-methyl), haloxyfop (including haloxyfop-methyl), hexazinone, hydantocidin, icafolin (including icafolin-methyl), imazamox (including R-imazamox), imazapic, imazapir, imazethapir, indaziflam, indolauxipir (including indolauxipir-cyanomethyl), iodosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron (including iofensulfuron-sodium), ioxinil, iptriazopiride, isoproturon, isoxaflutol, lancotrione, MCPA, MCPB, mecoprop-P,mesosulfurone (including mesosulfuron-methyl), mesotrione, metamitrone, metazachlor, methiozoline, metolachlor, metosulam, metribuzin, metsulfuron, napropamide, nicosulfurone, norflurazone, oxadiazone, oxasulfurone, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, fenmedifam, picloram, pinoxadene, pretilaclor, primisulfuron-methyl, promethrine, propanil, propaquizafop, propyrisulfurone, propizamide, prosulfocarb, prosulfurone, pyraclonil, piraflufen (including piraflufen-ethyl), pyraquinate, pyrasulfotol, pyridate, piriftalide, piriflubenzoxime, pirimisulfan, piroxasulfone, piroxsulam, quinclorac, quinmerac, quizalofop (including quizalofop-P, Petition 870250089696, dated 02 / 10 / 2025, page 28 / 73 14 / 55 ethyl and quizalofop-P-tefuryl), rimisoxafene, rimsulfurone, saflufenacil, sethoxydim, simazine, S-metallochloride, sulfentrazone, sulfosulfurone, tebutiurone, tefuryltrione, tembotrione, terbuthylazine, terbutrine, tetflupyrolimeth, thiencarbazone, tifensulfurone, tiafenacil, tolpyralate, topramezone, tralcoxidim, triafamonone, trialate, triasulfurone, tribenuron (including tribenuron-methyl), triclopyr, trifloxysulfurone (including trifloxysulfuronsodium), trifludimoxazine, trifluralin, triflusulfurone, tripyrasulfone, ethyl ester of the acid 3-(2-chloro-4-fluoro5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazol-5-carboxylic acid, 4-hydroxy-1-methoxy-5-methyl-3[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2pyridyl]imidazolidin-2-one, 5-ethoxy-4-hydroxy-1-methyl-3-[4(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one, (4R)1-(5-tert-butylisoxazol-3-yl)4-ethoxy-5-hydroxy-3-methylimidazolidin-2-one, 3-ethylsulfanyl-N-(1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, 3(isopropylsulfanylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, ethyl 2-[[3-[[3-chloro-5-fluoro-6-[3-methyl-2,6dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2pyridyl]oxy]acetato, 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]phenoxy]-2methoxy-acetato de methyla, 6-chloro-4-(2,7-dimethyl-1-naphthyl), Petition 870250089696, de 02 / 10 / 2025, p. 29 / 73 15 / 55 5-hydroxy-2-methyl-pyridazin-3-one, (2-fluorophenyl)methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylate, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)pyrimidine-4-carboxylic acid and 3[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]3a,4,5,6-tetrahydro-6-methyl-6aH-cyclopent[d]isoxazol-6acarboxylate methyl.

[0039] The mixing partners of the compound of Formula (I) may also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual”, Sixteenth Edition, British Crop Protection Council, 2012.

[0040] The compound of Formula (I) can also be used in mixtures with other agrochemicals such as fungicides, nematicides or insecticides, examples of which are given in The Pesticide Manual”.

[0041] The mixing ratio between the compound of Formula (I) and the mixing partner is preferably 1:100 to 1000:1.

[0042] Mixtures can be advantageously used in the formulations mentioned above (in which case “active ingredient” relates to the respective mixture of the compound of Formula (I) with the mixing partner).

[0043] The compounds or mixtures of the present invention can also be used in combination with one or more herbicidal plant protection agents. Examples of such plant protection agents include benoxacor, cloquintocet (including cloquintocetemexil), cyprosulfamide, dichlormide, fenchlorazole (including fenchlorazole-ethyl), fenchlorim, fluxofenim, furilazole, Petition 870250089696, dated 02 / 10 / 2025, page 30 / 73 16 / 55 isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifene and oxabetrinil.

[0044] Mixtures of a compound of Formula (I) with cyprosulfamide, isoxadifenoethyl, cloquintocete-mexil and / or metcamifene are particularly preferred.

[0045] The plant protection agents of the compound of Formula (I) may also be in the form of esters or salts, as mentioned, for example, in “The Pesticide Manual”, 16th Edition (BCPC), 2012. The reference to cloquintocet-mexil also applies to a lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salt thereof as disclosed in WO 02 / 34048.

[0046] Preferably, the mixing ratio between compound of Formula (I) and plant protectant is 100:1 to 1:10, especially 20:1 to 1:1.

[0047] The present invention further provides a method of controlling weeds at a locus, said method comprising applying to the locus an amount of weed control of a composition comprising a compound of Formula (I). Furthermore, the present invention may further provide a method of selectively controlling weeds at a locus comprising crop plants and weeds, wherein the method comprises applying to the locus an amount of weed control of a composition according to the present invention. “Control” means to kill, reduce or retard growth or prevent or reduce germination. It is noteworthy that the compounds of the present invention exhibit much improved selectivity compared to known structurally similar compounds. In general, the Petition 870250089696, dated 02 / 10 / 2025, page 31 / 73 17 / 55 plants to be controlled are unwanted plants (weeds). Locus means the area in which the plants are growing or will grow. Application may be applied to the locus pre-emergence and / or post-emergence of the crop plant. Some crop plants may be inherently tolerant to the herbicidal effects of the compounds in Formula (I). Preferred crop plants include corn, wheat, barley, soybeans, and rice.

[0048] The application rates of the compounds of Formula I may vary within wide limits and depend on the nature of the soil, the application method (pre- or post-emergence; seed covering; seed furrow application; no tillage application, etc.), the crop plant, the weed(s) to be controlled, the prevailing climatic conditions and other factors controlled by the application method, the timing of application and the target crop. The compounds of Formula I according to the invention are generally applied at a rate of 10 to 2500 g / ha, especially 25 to 1000 g / ha, more especially 25 to 250 g / ha.

[0049] Application is usually carried out by spraying the composition, typically by tractor-mounted sprayer for large areas, but other methods such as dusting (for powders), drip irrigation or irrigation can also be used.

[0050] Crop plants should be understood as also including those crop plants that have been made tolerant to other herbicides or classes of herbicides (e.g., ALS, GS, EPSPS, PPO, HPPD, PDS, and ACCase inhibitors) by conventional breeding methods or Petition 870250089696, dated 02 / 10 / 2025, page 32 / 73 18 / 55 by genetic manipulation. An example of a crop that has been made tolerant to imidazolinones, e.g., imazamox, by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been made herbicide-tolerant by genetic manipulation methods include, e.g., glyphosate- and glufosinate-resistant maize varieties, commercially available under the trade names RoundupReady® and LibertyLink®. The compounds of the present invention can also be used in conjunction with crops that are tolerant to SDPS-inhibiting herbicides, such as those taught in WO2020 / 236790.

[0051] Crop plants should also be understood as those that have been made resistant to harmful insects through genetic manipulation methods, for example Bt corn (resistant to the European corn borer), Bt cotton (resistant to the boll weevil) and also Bt potatoes (resistant to the Colorado potato beetle). Examples of Bt corn are the Bt 17 6 ​​corn hybrids from NK® (Syngenta). (Seeds). Bt toxin is a protein that is naturally formed by the soil bacterium Bacillus thuringiensis. Examples of toxins, or transgenic plants capable of synthesizing such toxins, are described in EP-A-451 878, EP-A-374 753, WO 93 / 07278, WO 95 / 34656, WO 03 / 052073 and EP-A-427 529. Examples of transgenic plants comprising one or more genes encoding insecticide resistance and expressing one or more toxins are KnockOut® (corn), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard®, and Protexcta®. Plant crops or seed material thereof may be both herbicide-resistant and resistant to... Petition 870250089696, dated 02 / 10 / 2025, page 33 / 73 19 / 55 feeding by insects (stacked transgenic events). For example, the seed may have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.

[0052] Cultivated plants should also be understood as including those obtained by conventional breeding or genetic manipulation methods and containing so-called output traits (e.g., improved storage stability, higher nutritional value and improved flavor).

[0053] The compositions can be used to control unwanted plants (collectively, “weeds”). The weeds to be controlled can be monocotyledonous species, for example Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum, and dicotyledonous species, for example Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium. The compounds and compositions of the present invention are particularly suitable for controlling the species Digitaria, Echinochloa, Eleusine, Lolium and Setaria.

[0054] In a further aspect of the present invention, the use of a compound of Formula (I) as defined herein as a herbicide is provided. Processes for preparing compounds of Formula (I)

[0055] The compounds of formula (II) are obtained by the Horner-Wadsworth-Emmons reaction of compounds of formula (III) with phosphonate esters of formula (IV), where R5 is Petition 870250089696, dated 02 / 10 / 2025, p. 34 / 73 20 / 55 a C1-C1 alkyl chain (e.g., methyl or ethyl), in the presence of a base (e.g., sodium hydride, sodium hexamethyldisylazide, n-butyllithium or sodium tert-butoxide), preferably in a suitable solvent (e.g., tetrahydrofuran, 1,2-dimethoxyethane, diethyl ether, N,N-dimethylformamide or dimethyl sulfoxide), preferably at temperatures between -78 °C and 80 °C. Scheme 1 (III) (V) (II)

[0056] The compounds of formula (III) are prepared by reducing compounds of formula (V) with a suitable reducing agent (e.g., sodium borohydride, lithium borohydride or diisobutylaluminum hydride), in a suitable solvent (e.g., methanol, ethanol or tetrahydrofuran) at temperatures between -78 °C and 30 °C, and optionally in the presence of a cosolvent such as dichloromethane. Scheme 2 (V) (III)

[0057] The compounds of formula (V) are prepared by adding anhydrides (VI) with amines (VII), or salts thereof, in a suitable solvent (e.g., polyethylene glycol Petition 870250089696, dated 02 / 10 / 2025, p. 35 / 73 21 / 55 400, toluene, N,N-dimethylformamide or dimethyl sulfoxide), at temperatures between 20 °C and 140 °C, optionally in the presence of an acid such as acetic acid, or a base such as triethylamine. Scheme 3 1¾ nh2 (VI) (VII) (V)

[0058] The compounds of formula (VI) are commercially available or can be prepared from diacids (VIII), in the presence of an acylating agent (e.g., acetic anhydride, trifluoroacetic anhydride or acetyl chloride) at temperatures between 20 °C and 140 °C, optionally in a suitable solvent (e.g., tetrahydrofuran, toluene, dichloromethane, isopropyl acetate) and optionally in the presence of a base (e.g., sodium acetate or sodium hydroxide) or alternatively under conditions described in the literature for a condensation reaction such as phosphorus pentoxide in a suitable solvent (e.g., dichloromethane). Scheme 4 (VIII) (VI)

[0059] The compounds of formula (IX) are obtained by thionation reaction of compounds of formula (II), with a thionation reagent (e.g., Lawesson's reagent or P2S5), optionally Petition 870250089696, dated 02 / 10 / 2025, page 36 / 73 22 / 55 in the presence of a base (e.g., sodium bicarbonate or triethylamine), preferably in a suitable solvent (e.g., tetrahydrofuran, toluene, acetonitrile or dichloromethane), preferably at temperatures between 20 °C and 120 °C.

[0060] Alternatively, compounds of formula (X) in which the relative stereochemistry is cis- with respect to the stereocenters at C(1) and C(5) , can be prepared by reduction of compounds of formula (XI). Suitable conditions include reduction using a silane (e.g., triethylsilane), in combination with an acid (e.g., trifluoroacetic acid), preferably in the presence of a suitable solvent (e.g., dichloromethane), preferably at temperatures between 0 °C and 40 °C. of formula (XI) by cyclization of Compounds of formula (XII) may be prepared, preferably in the presence of an acid (e.g., acid pPetição 870250089696, dated 02 / 10 / 2025, page 37 / 73 23 / 55 toluenesulfonic acid), preferably in the presence of a solvent (e.g., 1,2-dichloroethane), preferably at temperatures between 20 °C and 120 °C. Scheme 7 (XII)

[0062] Compounds of formula (XI) (XII) can be prepared (XIII) by reaction with an amine of formula (VII), preferably in a solvent (p. e.g., toluene), preferably at temperatures between 20 °C and 120 °C. Scheme 8 formula prepared according to methods described in the literature, e.g. For example, Australian Journal of Chemistry, 1982, vol. 35, # 9, pp. 1903-1911.

[0064] Where compounds are prepared as a mixture of diastereomers, they can be separated by techniques commonly employed by someone skilled in the art, for example, flash column chromatography or HPLC. Petition 870250089696, dated 02 / 10 / 2025, page 38 / 73 24 / 55 preparative. When compounds are prepared as racemic mixtures, they can be separated by techniques that are commonly employed by a person skilled in the art, for example preparative HPLC using a chiral stationary phase or chiral resolution (e.g., through the formation of diastereomeric salts).

[0065] The following non-limiting examples provide specific synthesis methods for representative compounds of the present invention, as presented in the Tables below. LCMS methods: Method 1:

[0066] Spectra were recorded on a Waters Mass Spectrometer (SQD2 or QDA single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: Positive and Negative Polarity Switching), Capillary: 0.8-3.00 kV, Cone Range: 25, Source Temperature: 120-150 °C, Desolvation Temperature: 500-600 °C, Cone Gas Flow: 50 L / h, Desolvation Gas Flow: 1000 L / h, Mass Range: 110 to 850 Da) and a Waters Acquity UPLC: Quaternary solvent manager, heated column compartment, diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8 µm, 30 x 2.1 mm, Temp: 40 °C, DAD wavelength range (nm): 200 to 400, Solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 0 min B at 10%; 0-0.2 min B at 10-50%; 0.2-0.6 min B at 50-100%; 0.6-1.3 min B at 100%; 1.3-1.4 min B at 100-10%; 1.4-1.6 min B at 10%; Flow rate (mL / min) 0.6. Petition 870250089696, dated 02 / 10 / 2025, page 39 / 73 25 / 55 Example 1: Acid 2-[(IR*,2S*,5S*)-3-[(2,3difluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2yl]acetic acid (Compound A.04) Step A: Preparation of 3-[(2,3-difluorophenyl)methyl]-3-azabicyclo[3.1.0]hexane-2,4-dione

[0067] To a solution of 3-oxabicyclo[3.1.0]hexane-2,4-dione (1.00 g, 8.92 mmol) in polyethylene glycol 400 (2.00 g, 4.71 mmol), (2,3-difluorophenyl)methanamine (1.27 g, 8.92 mmol) was added. The reaction was heated at 120 °C for 18 hours before being cooled to room temperature and diluted with EtOAc (20 mL) and water (30 mL). The layers were separated and the aqueous layer was extracted with EtOAc (20 mL) and the combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue obtained after concentration was purified by silica gel column chromatography (gradient of 0-60% ethyl acetate in cyclohexane) to provide 3-[(2,3-difluorophenyl)methyl]-3-(Petition 870250089696, dated 02 / 10 / 2025, page 40 / 73). 26 / 55 azabiciclo[3.1. Ο]hexane-2,4-dione (43%, 900 mg) as a colorless solid. LC-MS (method 1): Tr1.27, m / z = 238 (M+H)+. ^-NMR (400 MHz, CDC13, ppm) δ 7.10 (d 1, 1H), 7.06 6.98 (m, 2H), 4.65 - 4.61 (m, 2H), 2.53 (dd, 2H), 1.56 (td, 1H), 1.40 (dt, 1H). Step B: Preparation of 3-[(2,3-difluorophenyl)methyl]-4-hydroxy-3-azabicyclo[3.1.0]hexan-2-one F

[0068] To a stirred solution of 3—[(2,3—difluorophenyl)methyl]-3-azabicyclo[3.1.0]hexane-2,4-dione (300 mg, 1.26 mmol) in methanol (10 mL), sodium borohydride (95.7 mg, 2.53 mmol, 2.00 equiv.) was added at room temperature. The reaction was stirred for 2 hours before being quenched with water (10 mL). EtOAc (20 mL) was added and the layers were separated. The aqueous portion was extracted with EtOAc (20 mL) and the combined organic portions were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (0-80% ethyl acetate gradient in cyclohexane) to give 3-[(2,3-difluorophenyl)methyl]-4-hydroxy-3-azabicyclo[3.1.0]hexan-2-one (93%, 280 mg) as a gummy mass. LC-MS (method 1): Tr0.94, m / z = 240 (M+H)+. Petition 870250089696, dated 02 / 10 / 2025, page 41 / 73 27 / 55 i-H-RMN (400 MHz, CDCI3, ppm) δ 6,98 - 7,14 (m, 3H) , 4,90 - 4,84 (m, 1H) , 4,81 - 4,59 (m, 1H) , 4,38 - 4,29 (m, 1 H) , 2,05 - 1, 96 (m, 2H) , 1,19 - 1,09 (m, 1H), 0,56 - 0,50 (m, 1H) . Passo C :2- [3- [ (2,3-difluorofenil)metil] -4-oxo-3azabiciclo[3.1.0]hexan-2-il]acetato de metila F

[0069] To a solution of methyl diethylphosphonoacetate (1.05 g, 5 mmol) in 1,2-dimethoxyethane (30 mL) at 0 °C, sodium hydride (200 mg, 5 mmol, 60% by mass in mineral oil) was added. The mixture was stirred for 20 minutes before the dropwise addition of a solution of 3-[(2,3-difluorophenyl)methyl]-4-hydroxy-3-azabicyclo[3.1.0]hexan-2one (800 mg, 3.34 mmol) in 1,2-dimethoxyethane (5 mL). The resulting mixture was slowly heated to room temperature and stirred for 18 hours before being poured into cold water (15 mL). The mixture was diluted with EtOAc (20 mL) and the layers were separated. The aqueous portion was extracted with EtOAc (20 mL) and the combined organic portions were washed with aqueous saturated NaCl solution (50 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (0-80% ethyl acetate gradient in cyclohexane) to provide: Petição 870250089696, de 02 / 10 / 2025, pág. 42 / 73 28 / 55 2- [ (lR*,2R*,55*)-3-[ (2,3-difluorofenil)metil] -4-oxo-3azabiciclo[3.1.0]hexan-2-il]acetato de metila (10%, 95 mg) (Composto A.07) LC-MS (método 1): Tr1,03, m / z = 296 (M+H)+. ^-RMN (400 MHz, CDC13, ppm) δ 7,14 - 7,01 (m, 3H) , 4,71 - 4,65 (m, 1H) , 4,19 - 4,12 (m, 1H) , 4,05 (dt, 1H) , 3,72 (s, 3H), 2,75 (dd, 1H), 2,30 (dd, 1H), 2,20 - 2,14 (m, 1H), 2,05 (ddd, 1H), 1,05 (td, 1H), 0,73 - 0,69 (m, 1H); e 2- [ (lR*,2S*,5S*}-3-[ (2,3-dif luorof enil) metil ] -4-oxo-3azabiciclo[3.1.0]hexan-2-il]acetato de metila (20%, 210 mg) (Composto A.10) LC-MS (método 1): Tr1,03, m / z = 296 (M+H)+. ^-RMN (400 MHz, CDCI3, ppm) õ 7,14 - 7,03 (m, 2H) , 7,01 (d 1, 1H) , 4,83 (dd, 1H), 4,11 (d, 1H), 3,74 - 3,73(m, 1H) , 3,72 (s, 3H) , 2,78 (dd, 1H) , 2,52 (dd, 1H) , 2,00(d, 1H), 1,81 (td, 1H), 1,11 (dd, 1H), 0,53 - 0,48 (m,1H) Step Dj 2- ( (1R*, 25*, 55*) -3- [ (2,3-difluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2yl]acetic acid (Compound A. 04)

[0070] To a solution of 2-[(lR*,25*,55*)-3-[(2,3-difluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl]methyl acetate] (100 mg, 0.339 mmol) in tetrahydrofuran (4 mL) and water (1 mL) at room temperature, lithium hydroxide hydrate (17.0 mg, 0.406 Petition 870250089696, dated 02 / 10 / 2025, p. 43 / 73 29 / 55 mmol). The mixture was stirred for 3 h before the addition of water (5 mL) and EtOAc (5 mL). The organic portion was discarded and the pH of the aqueous portion was adjusted to pH 2 with 1 M HCl aq. and extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 2-[(1R*,2S*,5S*)-3[(2,3-difluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan2-yl]acetic acid (73%, 70 mg) as a colorless solid. LC-MS (method 1): Tr 0.95, m / z = 282 (M+H)+. 1H-NMR (400 MHz, DMSO-de, ppm) d 12.47 (s, 1H), 7.35(d, 1H), 7.21- 7.14 (m, 1H), 7.09 - 7.01 (m, 1H), 4.65 (d,1H), 4.10 (d, 1H), 3.56 (dd, 1H), 2.78 (dd, 1H), 2.40 (dd, 1H), 1.84 (dd, 1H), 1.79 - 1.73 (m, 1H), 1.06 (td, 1H), 0.35(q, 1H) Example 2j 2-[(1R*,2R*,5S*)-3-[(2,3,4-trifluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2yl]acetic acid (Compound A.13) Step A: Preparation of ethyl 3-oxo-3-[2-[(2,3,4-trifluorophenyl)methylcarbamoyl]cyclopropyl]propanoate Petition 870250089696, dated 02 / 10 / 2025, page 44 / 73 30 / 55

[0071] To a stirred solution of (2E)-2-(4-oxo-3oxabicyclo[3.1.0]hexan-2-ylidene)ethyl acetate (1.14 g, 5.90 mmol) in toluene (10 mL), (2,3,4-trifluorophenyl)methanamine (1.00 g, 5.90 mmol) was added. The resulting mixture was stirred at room temperature for 3 hours and then evaporated to dryness. The crude residue was purified by silica gel column chromatography (ethyl acetate-cyclohexane gradient) to give ethyl 3-oxo-3-[2-[(2,3,4-trifluorophenyl)methylcarbamoyl]cyclopropyl]propanoate (1.40 g, 65% yield). LC-MS (method 1): Tr 1.18, m / z = 344 (M+H)+. 1H-NMR (400 MHz, in DMSO, ppm) δ 1.15 (m, 1H) 1.161.25 (m, 3 H) 1.41 (td, J=6.60, 4.28 Hz, 1 H) 2.15 (td, J=8.77, 6.42 Hz, 1 H) 2.24 - 2.32 (m, 1 H) 3.48 (d, J=16.14 Hz, 1 H) 3.64 (d, J=16.14 Hz, 1 H) 4.01 - 4.13 (m, 2 H) 4.28 (d, J=5.75 Hz, 2 H) 7.12 - 7.19 (m, 1 H) 7.23 - 7.32 (m, 1 H) H) 8.72 (tl, J=5.75 Hz, 1H). Step B:Preparation of(2E) - 2- [4-oxo-3- [(2,3,4trifluorophenyl)methyl]-3-azabicyclo[3.1.0]hexane-2ylidene]ethyl acetate Petition 870250089696, of 02 / 10 / 2025, p. 45 / 73 31 / 55

[0072] To a stirred solution of 3-oxo-3-[2-[(2,3,4-trifluorophenyl)methylcarbamoyl]cyclopropyl]propanoate (1.40 g, 3.8 mmol) in 1,2-dichloroethane (15 mL), p-toluenesulfonic acid (210 mg, 1.2 mmol) was added. The reaction mixture was heated to 90 °C for 4 hours, then allowed to cool to room temperature and evaporated to dryness. The crude residue was purified by silica gel column chromatography (ethyl acetate-cyclohexane gradient) to give (2E)-2-[4-oxo-3-[(2,3,4-trifluorophenyl)methyl]-3-azabicyclo[3.1.0]hexan-2ylidene]ethyl acetate (1.10 g, 83% yield). LC-MS (method 1): Tr 1.11, m / z = 326 (M+H)+. 1H-NMR (400 MHz, CDCls, ppm) δ 1.06 (q, J=3.75 Hz, 1 H) 1.23 - 1.32 (m, 3 H) 1.52 - 1.58 (m, 1 H) 2.38 (ddd, J=8.50, 5.07, 3.56 Hz, 1 H) 3.60 - 3.65 (m, 1 H) 4.09 - 4.22 (m, 2 H) 4.55 (d, J=16.01 Hz, 1 H) 4.68 (d, J=16.01 Hz, 1 H) 5.15 (s, 1 H) 6.81 - 6.97 (m, 2 H). Step C: Ethyl 2-[(1R*,2R*,5S*)-3-[(2,3,4-trifluorophenyl)methyl]4-oxo-3-azabicyclo[3.1.0]hexan-2-yl]acetate (Compound A. 19) Petition 870250089696, dated 02 / 10 / 2025, p. 46 / 73 32 / 55

[0073] To a solution of (2E)-2-[4-oxo-3-[(2,3,4-trifluorophenyl)methyl]-3-azabicyclo[3.1.0]hexan-2-ylidene]ethyl acetate (200 mg, 0.61 mmol) in dichloromethane (2 mL) at -78 °C, trifluoroacetic acid (1.42 mL, 18.4 mmol) and triethylsilane (0.92 mL, 6.14 mmol) were added. The reaction mixture was stirred for 10 minutes, then refluxed at 40 °C for 7 hours. The reaction mixture was then quenched with aqueous NaHCO3 and extracted three times with ethyl acetate. The combined organics were dried over sodium sulfate, then filtered and evaporated to dryness. The crude residue was purified by silica gel column chromatography (ethyl acetate to cyclohexane gradient) to give 2-[(1R*,2R*,5S*)-3-[(2,3,4-trifluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2yl]ethyl acetate (152 mg, 76% yield). LC-MS (method 1): Tr 1.05, m / z = 328 (M+H)+. 1H-NMR (400 MHz, CDCl3, ppm) d 0.67 - 0.73 (m, 1 H) 1.29 (t, J=7.13 Hz, 3 H) 2.03 (ddd, J=8.72, 6.03, 3.13 Hz, H) 2.13 - 2.20 (m, 1 H) 2.30 (dd, J=15.95, 9.82 Hz, 1 H) 2.72 (dd, J=15.95, 4.44 Hz, 1 H) 4.01 - 4.21 (m, 4 H) 4.63 (d, J=15.63 Hz, 1 H) 6.93 - 7.06 (m,2H). Petition 870250089696, dated 02 / 10 / 2025, p. 47 / 73 33 / 55 Step D: 2- [ (1R*, 2R*, 5S*) -3- [ (2,3,4trifluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2yl]acetic acid (Compound A.13)

[0074] To a stirred solution of 2-[(IR*,2R*,5S*)-3[(2,3,4-trifluorophenyl)methyl]-4-oxo-3azabicyclo[3.1.0]hexan-2-yl]ethyl acetate] (100 mg, 0.31 mmol) in methanol (3 mL) at room temperature, sodium hydroxide (1 mL, 10% aqueous solution) was added. The mixture was stirred for 3 h. The reaction mixture was then concentrated under vacuum to remove the methanol, acidified to pH 2 with 2 N hydrochloric acid, and extracted three times with ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated under vacuum to give 2-[(IR*,2R*,5S*)-3-[(2,3,4-trifluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2yl]acetic acid (75 mg, 82% yield) as a colorless solid. LC-MS (method 1): Tr0.93, m / z = 300 (M+H)+. iH-NMR (400 MHz, DMSO-de, ppm) δ 0.92 - 0.99 (m, 1 H) 0.96 (td, J=8.10, 4.58 Hz, 1 H) 1.86 - 1.92 (m, 1 H) 2.06 2.12 (m, 1 H) 2.23 - 2.34 (m, 1 H) 2.64 - 2.70 (m, 1 H) 3.91 (dt, J=9, 60, 4, 98 Hz, 1 H) 4.09 (d, J=16.02 Hz, 1 H) 4.50 (d, J=16.14 Hz, 1 H) 7.01 - 7.08 (m, 1 H) 7.25 - 7.32 (m, 1 H) 12.45 (s, 1 H) Petition 870250089696, dated 02 / 10 / 2025, p. 48 / 73 34 / 55

[0075] TABLE 1 Examples of compounds of Formula (I) Compound Name of Compound Structure XH NMR (400 MHz, CDC13, unless indicated) A. 01 2-[(IR*,2R*,5S*)-3-[(2,3-difluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl]acetic acid F oh ^7 (DMSO-de): 12.58 - 12.33 (s, 1H), 7.45 - 7.29 (m, 1H), 7.23 - 7.16 (m, 1H), 7.09 - 6.94 (m, 1H), 4.71 - 4.48 (m, 1H), 4.15 - 4.08 (m, 1H), R 1H) Petition 870250089696, dated 02 / 10 / 2025, p. 49 / 73 35 / 55 Compound Name Compound Structure XH NMR (400 MHz, CDC13, unless indicated) A. 04 2-[(IR*,25*,55*)-3-[(2,3-difluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl]acetic acid F ...... OH (DMSO-de) : 12.47 (s, 1H), 7.35 (d, 1H), 7.21-7.14 (m, 1H), 7.09-7.01 (m, 1H), 4.65 (d, 1H), 4.10 (d, 1H), 3.56 (dd, 1H), 2.78 (dd, 1H), 2.40 (dd, 1H), 1.84 (dd, 1H), 1.79 - 1.73 (m, 1H), 1.06 (td, 1H), 0.35 (q, 1H) Petition 870250089696, dated 02 / 10 / 2025, pp. 50 / 73 36 / 55 Compound Name Compound Structure Ή NMR (400 MHz, CDC13, unless indicated) A. 07 2-[(1R*,2R*,5S*)-3-[(2,3-difluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl]methyl acetate F \ Γ o \ / h3cz 7.14 - 7.01 (m, 3H), 4.71 4.65 (m, 1H), 4.19 - 4.12 (m, 1H), 4.05 (dt, 1H), 3.72 (s, 3H), 2.75 (dd, 1H), 2.30 (dd, 1H), 2.20 - 2.14 (m, 1H), 2.05 (ddd, 1H) 1.05 (td, 1H), 0.73 - 0.69 (m, 1H) A. 10 2- [(IR*,2S* , 5S* ) -3- [ (2,3- difluorophenyl) methyl]-4-oxo- 3- azabicyclo [3.1 .0]hexan-2- FX^x ...... 0 \ / h3cz 7.14 - 7.03 (m, 2H), 7.01 (d 1, 1H), 4.83 (dd, 1H), 4.11 (d, 1H), 3.74 - 3.73 (m, 1H), 3.72 (s, 3H), 2.78 (dd, Petition 870250089696, dated 02 / 10 / 2025, pp. 51 / 73 37 / 55 Compound Name Compound Structure 1H NMR (400 MHz, CDCl3, unless indicated) methyl acetate 1H), 2.52 (dd, 1H), 2.00 (d, 1H), 1.81 (td, 1H), 1.11 (dd, 1H), 0.53 - 0.48 (m, 1H) A.13 2-[(1R*,2R*,5S*)-3-[(2,3,4-trifluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2yl]acetic acid FF 1 F \ Jr oh (DMSO-d 6): 0.92 - 0.99 (m, 1H) 0.96 (td, 1H) 1.86 - 1.92 (m, 1H) 2.06 - 2.12 (m, 1 H) 2.23 - 2.34 (m, 1 H) 2.64 - 2.70 (m, 1 H) 3.91 (dt, 1 H) 4.09 (d, 1 H) 4.50 (d, 1 H) 7.01 - 7.08 (m, 1 H) 7.25 - 7.32 (m, 1 Petition 870250089696, dated 02 / 10 / 2025, pp. 52 / 73 38 / 55 Compound Name Compound Structure 1H NMR (400 MHz, CDCl3, unless indicated) H) 12.45 (s, 1H) A.61 2[(1R*,2R*,5S*)-3-[(2-fluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl]acetic acid O^Z \ OH \ / (DMSO-d 6): 0.72 (q,1H) 0.96 (td, 1H) 2.04 - 2.12 (m, 1H) 2.23 (dd, 1H) 2.67 (dd, 1H) 3.87 (dt, 1H) 4.05 (d,1H) 4.52 (d, 1H), 7.14 - 7.22 (m, 3H) 7.29 - 7.37 (m, 1 H) 12.45 (sl, 1 H) Petition 870250089696, dated 02 / 10 / 2025, pp. 53 / 73 39 / 55 Compound Name Compound Structure 1H NMR (400 MHz, CDCl3, unless indicated) A.64 2[(1R*,2R*,5S*)-3-[(3-fluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl]acetic acid F OH (DMSO-d 6): 12.46 (sl, 1H) 7.34 - 7.41 (m, 1H) 7.09 (td, 1H) 6.97 - 7.05 (m, 2H) 4.49 (d, 1H) 3.99 (d, 1H) 3.85 (dt, 1H) 2.71 (dd, 1H) 1.97 - 2.21 (m, 2H) 1.89 (ddd, 1H) 0.94 (td, 1 H) 0.69 (q, 1 H) A.67 2[(1 R *,2 R *,5 S *) -3- [(4fluorophenyl)methyl]-4-oxo-3azabicyclo[3.1 .0]hexan-2yl]acetic acid \ Jr oh (DMSO-d 6): 12.45 (sl, 1 H) 7.22 (dd, 2 H) 7.15 (t, 2 H) 4.48 (d, 1 H) 3.94 (d, 1 H) 3.80 (dt, 1 H) Petition 870250089696, dated 02 / 10 / 2025, pp. 54 / 73 40 / 55 Petition 870250089696, dated 02 / 10 / 2025, pp. 55 / 73 41 / 55 Compound Name Compound Structure 1H NMR (400 MHz, CDCl3, unless indicated) 0.59-0.75 (m, 1H) A.73 2-[(1R*,2R*,5S*)-3-[(3,4-difluorophenyl)methyl]-4-oxo-3-azabicyclo[3.1.0]hexan-2-yl]acetic acid FO^Z \ OH (DMSO-d 6): 0.70 (q, 1H) 0.95 (td, 1H) 1.24 (s, 1H) 2.03 — 2.10 (m, 1H) 2.18 (dd, 1H) 2.69 — 2.76 (m, 1H) 3.86 (dt, 1H) 3.98 (d, 1H) 4.45 (d, 1 H) 7.04 (sl, 1 H) 7.21 - 7.28 (m, 1 H) 7.35 — 7.43 (m, 1 H) 12.44 (sl, 1 H) Petition 870250089696, dated 02 / 10 / 2025, pp. 56 / 73 42 / 55 Compound Name Compound Structure 1H NMR (400 MHz, CDCl3, unless indicated) A.76 2-[(1R*,2R*,5S*)-3-[(2-fluoro-4-chloro)methyl]4-oxo-3-azabicyclo[3.1.0]hexan-2yl]acetic acid o—- / \ oh (DMSO-d 6): 12.35 (s, 1H) 7.42 (dd, 1H) 7.18 - 7.25 (m, 2H) 4.03 - 4.48 (lq, 2H) 3.86-3.91 (qt, 1H) 2.62-2.67 (d ld, 1H) 2.21-2.27 (d ld, 1H) 2.05- 2.11 (m, 1 H) 1.86 - 1.90 (m, 1 H) 0.92-0.97 (m, 1 H) 0.7- 0.73(q, 1 H) A.79 acid 2- [(1 R *,2 R *,5 S *) -3-[(3-fluoro- 4- chloro)methyl]- 4-oxo-3- F 0.=- / \ oh \r (DMSO-d 6): 0.71 (q, 1 H) 0.95 (td, 1 H) 1.87 - 1.93 (m, 1 H) Petition 870250089696, dated 02 / 10 / 2025, pp. 57 / 73 43 / 55 Compound Name Compound Structure 1H NMR (400 MHz, CDCl3, unless otherwise indicated) azabicyclo[3.1.0]hexan-2yl]acetic 2.07 (dl, 1H) 2.19 (dd, 1H) 2.71 (dd, 1H) 3.87 (dt, 1H) 4.02 (d, 1H) 4.45 (d, 1H) 7.05 (ld, 1H) 7.22 (dl, 1H) 7.55 (t, 1H) 12.46 (sl, 1H) A.81 2[(1R*,2R*,5S*)-3-[(3-chloro-4-fluoro)methyl]4-oxo-3azabicyclo[3.1.0]hexan-2yl]acetic acid Cl OH \f (DMSO-d 6) 2.04 Petition 870250089696, dated 02 / 10 / 2025, pp. 58 / 73 44 / 55 Compound Name Compound Structure 1H NMR (400 MHz, CDCl3, unless otherwise indicated) - 2.22 (m, 2H) 1.85 - 1.94 (m, 1H) 1.20 - 1.28 (m, 1H) 0.95 (td, 1H) 0.69 (m, 1H) E.01 2-[(1R*,3aS*,7aR*)-2-[(2,3-difluorophenyl)methyl]-3-oxo-3a,4,5,6,7,7a-hexahydro-1H-isoindol-1-yl]acetic acid F (DMSO-d6): 0.88 - 1.01 (m, 2H) 1.02 - 1.14 (m, 1H) 1.37 - 1.46 (m, 1H) H) 1.47 - 1.57 (m, 2 H) 1.57 - 1.70 (m, 1 H) 1.99 - 2.10 (m, 1 H) 2.28 - 2.39 (m, 2 H) 2.52 - 2.62 (m, 2 H) 3.75 - 3.90 (m, 1 H) 4.25 - 4.37 (m, 1 H) 4.59 Petition 870250089696, dated 02 / 10 / 2025, pp. 59 / 73 45 / 55 Compound Name of Compound Structure 1H NMR (400 MHz, CDCl3, unless indicated) - 4.71 (m, 1H) 6.93 - 7.09 (m, 1H) 7.13 - 7.25 (m, 1H) 7.28 - 7.41 (m, 1H) 12.32 - 12.70 (m, 1H). E.04 2- [(1S*,3aS*,7aR * )-2-[(2,3-difluorophenyl) methyl]-3-oxo- 3 a ,4,5,6,7,7 a - hexahydro-1H- isoindol-1yl]acetic acid FN (DMSO-d 6): 0.66 - 0.82 (m, 1 H) 0.83 - 0.99 (m, 1 H) 0.99 - 1.13 (m, 1 H) 1.34 - 1.51 (m, 3 H) 1.52 - 1.63 (m, 1 H) 1.91 - 1.99 (m, 1 H) 2.00 - 2.10 (m, 1 H) 2.40 - 2.48 (m, 1 H) 2.57 - 2.66 (m, 1 H) Petition 870250089696, dated 02 / 10 / 2025, pp. 60 / 73 46 / 55 Compound Name NMR Structure (400 MHz, CDC13, unless otherwise indicated) 2.66 - 2.75 (m, 1 H) 3.04 - 3.18 (m, 1 H) 4.08 - 4.24 (m, 1 H) 4.72 - 4.91 (m, 1 H) 7.10 - 7.27 (m, 2 H) 7.30 - 7.42 (m, 1 H) 12.24 - 12.57 (m, 1 H) AE TABLES

[0076] Specific examples of compounds of Formula (I) are illustrated in Tables A to E below: Table A provides 60 compounds (A. 01 to A. 60) of Formula (I):

[0077] Where X = CH2; and where the values ​​of Y, n, R1e Q, are as defined in Table A below: Table A Petition 870250089696, dated 02 / 10 / 2025, pp. 61 / 73 47 / 55 Y n R1 Q Relative stereochemistry Absolute stereochemistry A.01 O 1 -H 2,3- difluorophenyl Cis- Rac- A.02 O 1 -H 2,3- difluorophenyl Cis- Ent-1 A.03 O 1 -H 2,3- difluorophenyl Cis- Ent-2 A.04 O 1 -H 2,3- difluorophenyl Trans- Rac- A.05 O 1 -H 2,3- difluorophenyl Trans- Ent-1 A.06 O 1 -H 2,3- difluorophenyl Trans- Ent-2 A.07 O 1 -CH3 2,3- difluorophenyl Cis- Rac- A.08 O 1 -CH3 2,3- difluorophenyl Cis- Ent-1 A.09 O 1 -CH3 2,3- difluorophenyl Cis- Ent-2 A.10 O 1 -CH3 2.3- difluorophenyl Trans- Rac- A.11 O 1 -CH3 2,3- difluorophenyl Trans- Ent-1 A.12 O 1 -CH3 2,3- difluorophenyl Trans- Ent-2 A.13 O 1 -H 2,3,4- trifluorophenyl Cis- Rac- Petition 870250089696, dated 02 / 10 / 2025, p. 62 / 73 48 / 55 A.14 O 1 -H 2,3,4- trifluorophenyl Cis- Ent-1 A.15 O 1 -H 2,3,4- trifluorophenyl Cis- Ent-2 A.16 O 1 -H 2,3,4- trifluorophenyl Trans- Rac- A.17 tri F - En - 1,3 - A.18 O 1 -H 2,3,4- trifluorophenyl Trans- Ent-2 A.19 O 1 -CH3 2,3,4- trifluorophenyl Cis- Rac- A.20 O 1 -CH3 2,3,4- trifluorophenyl Cis 2f Cis- Ent-1 A.24 O 1 Ent-2 A.22 O 1 -CH3 2,3,4- trifluorophenyl Trans- Rac- A.23 O 1 -CH3 2,3,4- trifluorophenyl Trans- Ent-1 A.24 O 1 -CH3 2,3,5- trifluorophenyl Trans- O 2 trifluoro, 1 A.25 Cis- Rac- A.26 O 1 -H 2,3,5-trifluorophenyl Cis- Ent-1 A.27 O 1 -H 2,3,5- trifluorophenyl Cis- Ent-2 Petition 870250089696, dated 02 / 10 / 2025, p. 63 / 73 49 / 55 A.28 O 1 -H 2,3,5- trifluorofenila Trans- Rac- A.29 O 1 -H 2,3,5- trifluorofenila Trans- Ent-1 A.30 O 1 -H 2,3,5- trifluorofenila Trans- Ent-2 A.31 O 1 -CH3 2,3,5- trifluorofenila Cis- Rac- A.32 O 1 -CH3 2,3,5- trifluorofenila Cis- Ent-1 A.33 O 1 -CH3 2,3,5- trifluorofenila Cis- Ent-2 A.34 O 1 -CH3 2,3,5- trifluorofenila Trans- Rac- A.35 O 1 -CH3 2,3,5- trifluorofenila Trans- Ent-1 A.36 O 1 -CH3 2,3,5- trifluorofenila Trans- Ent-2 A.37 S 1 -H 2,3- difluorofenila Cis- Rac- A.38 S 1 -H 2,3- difluorofenila Cis- Ent-1 A.39 S 1 -H 2,3- difluorofenila Cis- Ent-2 A.40 S 1 -H 2,3- difluorofenila Trans- Rac- A.41 S 1 -H 2,3- difluorofenila Trans- Ent-1 Petição 870250089696, de 02 / 10 / 2025, pág. 64 / 73 50 / 55 A.42 S 1 -H 2,3- difluorophenyl Trans- Ent-2 A.43 S 1 -CH3 2,3- difluorophenyl Cis- Rac- A.44 S 1 -CH3 2,3- difluorophenyl Cis- Ent-1 A.45 S 1 -CH3 2,3- difluorophenyl Cis- Ent-2 A.46 S 1 -CH3 2,3- difluorophenyl Trans- Rac- A.47 S 1 -CH3 2,3- difluorophenyl Trans- Ent-1 A.48 S 1 -CH3 2,3- difluorophenyl Trans- Ent-2 A.49 O 2 -H 2,3- difluorophenyl Cis- Rac- A.50 O 2 -H 2,3- difluorophenyl Cis- Ent-1 A.51 O 2 -H 2,3- difluorophenyl Cis- Ent-2 A.52 O 2 -H 2,3- difluorophenyl Trans- Rac- A.53 O 2 -H 2,3- difluorophenyl Trans- Ent-1 A.54 O 2 -H 2,3- difluorophenyl Trans- Ent-2 A.55 O 2 -CH3 2,3- difluorophenyl Cis- Rac- Petition 870250089696, 02 / 10 / 2025, pág. 65 / 73 51 / 55 A.56 O 2 -CH3 2,3- difluorophenyl Cis- Ent-1 A.57 O 2 -CH3 2,3- difluorophenyl Cis- Ent-2 A.58 O 2 -CH3 2,3- difluorophenyl Trans- Rac- A.59 O En2-1 -CH3 difluoro O 2 -CH3 2,3- difluorophenyl Trans- Ent-2 A.61 O 1 -H 2-fluorophenyl Cis- Rac- A.62 O 1 -H 2-fluorophenyl Cis- Ent-1 A.63 O 1 -H 2-fluorophenyl Cis.6H- Ent- Cis- Rac- A.65 O 1 -H 3-fluorophenyl Cis- Ent-1 A.66 O 1 -H 3-fluorophenyl Cis- Ent-2 A.67 O 1 -H 4-fluorophenyl Cis- Rac- A.68 O 1 -H 4-H Cis -En-fluorophenyl 4-fluorophenyl Cis- Ent-2 A.70 O 1 -H 3-chlorophenyl Cis- Rac- A.71 O 1 -H 3-chlorophenyl Cis- Ent-1 A.72 O 1 -H 3-chlorophenyl Cis- Ent-2 A.77 Oc -4 A.4 -H 1 -H 3,4-difluorophenyl Cis- Ent-1 A.75 O 1 -H 3,4- difluorophenyl Cis- Ent-2 Petition 870250089696, dated 02 / 10 / 2025, p. 66 / 73 52 / 55 A.76 O 1 -H 2-fluoro-4- chloro Cis- Rac- A.77 O 1 -H 2-fluoro-4chloro Cis- Ent-1 A.78 O 1 -H 2-fluoro-4chloro Cis- Ent-2 A.79 O 1 -H 3-fluoro-4chloro Cis- Rac- A.80 O 1 -H 3-fluoro-4chloro Cis- Ent-1 A.81 O 1 -H 3-fluoro-4chloro Cis- Ent-2 A.82 O 1 -H 3-chloro-4fluoro Cis- Rac- A.83 O 1 -H 3-chloro-4fluoro Cis- Ent-1 A.84 O 1 -H 3-chloro-4fluoro Cis- Ent-2

[0078] Table B provides 84 compounds (B.01 to B.84) of formula (I) wherein X = C(CH3)2; and wherein the values ​​of Y, n, R1 and Q are defined as in Table A above.

[0079] Table C provides 84 compounds (c.01 to C.84) of formula (I) in which X = CH2CH2; and in which the values ​​of Y, n, R1 and Q are defined as in Table A above.

[0080] Table D provides 84 compounds (D.01 to D.84) of formula (I) wherein X = CH2CH2CH2; and wherein the values ​​of Y, n, R1 and Q are defined as in Table A above.

[0081] Table E provides 84 compounds (E.01 to E.84) of formula (I) wherein X = CH2CH2CH2CH2; and wherein the values ​​of Y, n, R1 and Q are defined as in Table A above. Petition 870250089696, dated 02 / 10 / 2025, pp. 67 / 73 53 / 55 Biological Examples

[0082] Seeds of a variety of test species are sown in standard soil in pots Amaranthus palmeri (AMAPA), Amaranthus retroflexus (AMARE), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE). After cultivation for one day (pre-emergence) or after 8 days of cultivation (post-emergence) under controlled conditions in a greenhouse (24 / 16 °C, day / night; 14 hours of light; 65% humidity), the plants are sprayed with an aqueous spray solution derived from dissolving the technical active ingredient in a small amount of acetone and a special solvent and emulsifier mixture called IF50 (Emulsogen EL360™ at 11.12% + N-methylpyrrolidone at 44.44% + Dowanol DPM glycol ether at 44.44%, which was then diluted to the required concentration using Genapol XO80 at 0.2% (CAS No. 9043-30-5) in water as the diluent. The compounds are applied at the indicated rates.The test plants are then grown in a greenhouse under controlled conditions (24 / 16 °C, day / night; 14 hours of light; 65% humidity) and watered twice daily. After 13 days for pre- and post-emergence, the test is evaluated for the percentage of damage caused to the plant. Biological activities are shown in the following table on a five-point scale (5 = 81-100%; 4 = 61-80%; 3 = 41-60%; 2 = 21-40%; 1 = 0-20%; NT = not tested).

[0083] Table B1: Pre-emergency application Compost Rate (g / Ha) SETFA ECHCG AMAPA AMARE IPOHE A.01 1000 5 4 2 4 2 A.02 1000 5 5 2 5 2 Petition 870250089696, dated 02 / 10 / 2025, pages 68 / 73 54 / 55 A.03 1000 4 2 1 1 3 A.04 1000 3 2 2 2 1 A.07 1000 5 4 3 4 2 A.10 1000 4 1 2 2 1 A.13 1000 5 3 3 4 4 A.61 1000 5 3 4 5 4 A.64 1000 5 4 4 5 4 A.67 1000 3 3 4 3 4 A.70 1000 5 4 1 2 1 A.73 1000 5 3 3 4 4 A.76 1000 3 1 3 1 4 A.79 1000 4 2 1 1 1 A.82 1000 4 1 2 2 1 E.01 1000 1 2 3 3 NT E.04 1000 3 1 4 4 1

[0084] Table B2: Post-emergency application Compound Rate (g / Ha) SETFA ECHCG AMAPA AMARE IPOHE A.01 1000 5 4 2 4 3 A.02 1000 5 5 2 4 1 A.03 1000 4 2 1 3 3 A.04 1000 4 3 1 1 1 A.07 1000 4 3 3 3 3 A.10 1000 4 2 1 2 2 A.13 1000 5 3 2 3 2 A.61 1000 5 3 3 4 3 A.64 1000 5 3 3 4 3 A.67 1000 4 2 3 1 2 A.70 1000 4 3 3 1 1 Petition 870250089696, dated 02 / 10 / 2025, pp. 69 / 73 55 / 55 A.73 1000 4 3 1 2 1 A.76 1000 3 1 1 1 2 A.79 1000 4 1 1 1 1 A.82 1000 4 1 1 2 2 E.01 1000 1 1 1 1 1 E.04 1000 1 1 1 1 1

Claims

1. Compound of Formula (I) characterized in that X = -(CR2R3)m-; Y = 0 or S; Q is phenyl optionally substituted by 1 to 4 substituents R4; R1 is hydrogen or C1-Ce alkyl; R2 and R3 are independently selected from the group consisting of hydrogen, methyl, fluorine and chlorine; R4 halogen, cyano, C1-Ce-alkyl, C1-Ce-alkoxy-, C1-Ce-haloalkyl, C1-Ce-haloalkoxy- and -S (0) pC1-Ce-alkyl; m = 1, 2, 3 or 4; n = 1 or 2; ep = 0, 1 or 2.

2. Compound according to claim 1, characterized in that Y is 0.

3. Compound according to claim 1, characterized in that X is -(CR2R3)-.

4. Compound according to claim 2, characterized in that X is -(CH2)-.

5. Compound, according to any one of claims 1, 2, 3 or 4, characterized in that Q is replaced by one, two or three R4. Petition 870250089696, dated 02 / 10 / 2025, pp. 71 / 73 2 / 2 6. Compound according to any one of claims 1, 2, 3, 4 or 5, characterized in that Q is 2,3-difluorophenyl.

7. Compound according to any one of claims 1, 2, 3, 4, 5 or 6, characterized in that R1 is hydrogen or methyl.

8. Herbicidal composition characterized in that it comprises a compound, as defined in any one of claims 1, 2, 3, 4, 5, 6 or 7, and an agriculturally acceptable formulation adjuvant.

9. Herbicidal composition, according to claim 8, characterized in that it additionally comprises at least one additional pesticide.

10. Herbicidal composition, according to claim 9, characterized in that the additional pesticide is a herbicide or herbicide plant protectant.

11. A method for controlling weeds in a specific location, characterized in that it comprises applying to the location a quantity of weed control of a composition, as defined in any one of claims 8, 9 or 10.

12. Use of a compound of Formula (I), as defined in claim 1, characterized in that it is as a herbicide.