WO2024149675A1 - Herbicidal imidazole compounds - Google Patents

Abstract

The present invention relates to compounds of Formula (I) or an agronomically acceptable salt of said compounds wherein Q, R¹, R², R³ and m are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I) and to the use of compounds of Formula (I) for controlling weeds, in particular in crops of useful plants.

Description

HERBICIDAL IMIDAZOLE COMPOUNDS The present invention relates to novel herbicidal compounds, to processes for their preparation, to herbicidal compositions which comprise the novel compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth. WO2022/101270 discloses herbicidal N-heteroaryl pyrazole compounds. WO2023/066783 discloses herbicidal imizadole compounds featuring a pyrimidine ring. Thus, according to the present invention there is provided a compound of Formula (I):

or an agronomically acceptable salt thereof, wherein Q is phenyl or a C-linked 6-membered heteroaryl wherein said phenyl or 6- membered heteroaryl is optionally substituted by one or more (e.g one or two) R⁴; R¹ is independently selected from the group consisting of halogen, -CN, NO₂, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, - S(O)_pC₁-C₄alkyl, C₁-C₄alkoxy-, -C(O)C₁-C₄alkyl, -C(O)OC₁-C₄alkyl, C₁- C₄haloalkoxy and C₁-C₄alkoxyC₁-C₃alkyl-; R² is selected from the group consisting of halogen, -CN, NO₂, C₁-C₄alkyl, C₁- C₄haloalkyl, C₁-C₄alkoxy, -C(O)C₁-C₄alkyl, -C(O)OC₁-C₄alkyl, C₁- C₄haloalkoxy, C₁-C₄alkoxyC₁-C₃alkyl-, C₁-C₄alkoxyC₁-C₃alkoxy-, C₁-

R³ is selected from the group consisting of hydrogen, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkoxyC₁-C₃alkyl-, C₁- , C₁- C₃alkoxyC₁-C₃alkyl-, -CN, NO₂, C₂- -S(O)_pC₁-C₄haloalkyl, -C(O)OC₁-

R⁴ is selected from the group consisting of halogen, C₁-C₄ alkyl, C₁- C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄alkoxyC₁-C₃alkyl-, C₁- C₃alkoxyC₁-C₃alkyl-, -CN, NO₂, C₂- -S(O)_pC₁-C₄haloalkyl, -C(O)OC₁-

R⁵ is hydrogen or C1-C4alkyl; R⁶ is hydrogen or C1-C4alkyl; R⁷ is hydrogen or C1-C4alkyl; R⁸ is hydrogen or C₁-C₂alkyl; m = is 0, 1 or 2; and p = 0, 1 or 2. C₁-C₄alkyl- and C₁-C₆alkyl- includes, for example, methyl (Me, CH₃), ethyl (Et, C₂H₅), n-propyl (n-Pr), isopropyl (i-Pr), n-butyl (n-Bu), isobutyl (i-Bu), sec-butyl and tert-butyl (t-Bu). C₁-C₂alkyl is methyl (Me, CH₃) or ethyl (Et, C₂H₅). C2-C4alkenyl- includes, for example, -CH=CH2 (vinyl) and -CH2-CH=CH2 (allyl). C₂-C₄alkynyl- refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to four carbon atoms, and which is attached to the rest of the molecule by a single bond. Examples of C_2-C₄alkynyl include, but are not limited to, prop-1-ynyl, propargyl (prop-2-ynyl), and but-1-ynyl. Halogen (or halo) includes, for example, fluorine, chlorine, bromine or iodine. The same correspondingly applies to halogen in the context of other definitions, such as haloalkyl. C₁-C₄haloalkyl- includes, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2- fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3- tetrafluoropropyl and 2,2,2-trichloroethyl and heptafluoro-n-propyl. C₁-C₂haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, or 1,1-difluoro-2,2,2-trichloroethyl. C1-C6alkoxy includes methoxy and ethoxy. 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. C1-C4alkoxyC1-C3alkyl- includes, for example, methoxymethyl-. C1-C4alkoxyC1-C3alkoxy- includes, for example, methoxyethoxy-. C1-C4alkoxyC1-C3alkoxyC1-C3alkyl- includes, for example, meth- oxyethoxymethyl-. C3-C6cycloalkyl includes cyclopropyl, cyclopentyl and cyclohexyl. C1-C4alkyl-S- (alkylthio) includes, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio. C₁-C₄alkyl-S(O)- (alkylsulfinyl) includes, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec- butylsulfinyl or tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl. C₁-C₄alkyl-S(O)₂- (alkylsulfonyl) includes, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec- butylsulfonyl or tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl. In one embodiment of the present invention, R³ is hydrogen. In one embodiment of the present invention, there is provided a compound of Formula (I), wherein m is 1 or 2 and R¹ is independently selected from the group consisting of halogen (e.g F, Cl or Br), -CN, C₁-C₄alkyl (e.g Me), C₁-C₄haloalkyl (e.g CHF₂ or CF₃), C₁-C₄alkoxy- (e.g MeO-) and C₁-C₄haloalkoxy (e.g CF₃O-, CHF₂O-). In another embodiment of the present invention m is 1. In another embodiment of the present invention m is 2. In a preferred embodiment of the present invention, m is 1 and R¹ is halogen (e.g chloro). In another preferred embodiment of the present invention, R² is C1- C4haloalkyl (preferably -CF3 or -CF2H). In another embodiment of the present invention, Q is selected from the group consisting of:

wherein n is 0, 1 or 2. In a preferred embodiment of the present invention, Q is Q-1 or Q-3. Thus, in a more preferred embodiment of the present invention the compound of Formula (I) is of Formula (Ia’) or Formula (Ib’):

In another preferred embodiment, n is 1. In this embodiment, R⁴ is preferably selected from the group consisting of cyano, methyl, halogen and -CF₃. In a particularly preferred embodiment, Q is 4-Cl-phenyl-. In another embodiment of the present invention, Q is Q-3 and n is 2. Thus, in a more preferred embodiment of the present invention the compound of Formula (I) is a compound of Formula (Iba):

wherein R^4a is halogen, preferably fluoro or chloro and R^4b, preferably fluoro or chloro; and wherein R¹, R² and R³ are as defined in Formula (I). In a more preferred embodiment, there is provided a compound of Formula (Iba) wherein m is 1 and R¹ is chloro, R² is -CF₃ or -CF₂H and R³ is hydrogen. Compounds of Formula (Iba’) are particularly preferred in the context of the present invention as they typically exhibit improved crop selectivity, particularly in maize. Compounds of Formula (I) may contain asymmetric centres and may be present as a single enantiomer, pairs of enantiomers in any proportion or, where more than one asymmetric centre are present, contain diastereoisomers in all possible ratios. Typically one of the enantiomers has enhanced biological activity compared to the other possibilities. The present invention also provides agronomically acceptable salts of compounds of Formula (I). Salts that the compounds of Formula (I) may form with amines, including primary, secondary and tertiary amines (for example ammonia, dimethylamine and triethylamine), alkali metal and alkaline earth metal bases, transition metals or quaternary ammonium bases are preferred. The compounds of Formula (I) according to the invention can be used as herbicides by themselves, but they are generally formulated into herbicidal compositions using formulation adjuvants, such as carriers, solvents and surface- active agents (SAA). Thus, the present invention further provides a herbicidal composition comprising a herbicidal compound according to any one of the previous claims and an agriculturally acceptable formulation adjuvant. The composition can be in the form of concentrates which are diluted prior to use, although ready-to-use compositions can also be made. The final dilution is usually made with water, but can be made instead of, or in addition to, water, with, for example, liquid fertilisers, micronutrients, biological organisms, oil or solvents. The herbicidal compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, compounds of Formula I and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance. The compositions can be chosen from a number of formulation types. These include an emulsion concentrate (EC), a suspension concentrate (SC), a suspo- emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion, oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oil miscible flowable (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 instance will depend upon the particular purpose envisaged and the physical, chemical and biological properties of the compound of Formula (I). Soluble powders (SP) may 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 sulphate) 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 water dispersibility/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water soluble granules (SG). Wettable powders (WP) may 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 the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to form water dispersible granules (WG). Granules (GR) may be formed either by granulating a mixture of a compound of Formula (I) and one or more powdered solid diluents or carriers, or from pre- formed blank granules by absorbing a compound of Formula (I) (or a solution thereof, in a suitable agent) in a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of Formula (I) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and sticking 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). Dispersible Concentrates (DC) may 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 surface-active agent (for example to improve water dilution or prevent crystallisation in a spray tank). Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may 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 Trade Mark), 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), dimethyl amides of fatty acids (such as C8-C10 fatty acid dimethylamide) and chlorinated hydrocarbons. An EC product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of Formula (I) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70^oC) or in solution (by dissolving it in an appropriate solvent) and then emulsifying the resultant liquid or solution into water containing one or more SAAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents which have a low solubility in water. Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SAAs, to produce spontaneously a thermodynamically stable isotropic liquid formulation. A compound of Formula (I) is present initially in either the water or the solvent/SAA blend. Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs. An ME may be either an oil-in-water or a water-in-oil system (which system is present may 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 into water, either remaining as a microemulsion or forming a conventional oil- in-water emulsion. Suspension concentrates (SC) 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 bead milling the solid compound of Formula (I) in a suitable medium, optionally with one or more dispersing agents, to produce a fine particle suspension 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 milled and added to water, containing agents hereinbefore described, to produce the desired end product. Aerosol formulations comprise a compound of Formula (I) and a suitable propellant (for example n-butane). A compound of Formula (I) may also be dissolved or dispersed in a suitable medium (for example water or a water miscible liquid, such as n-propanol) to provide compositions for use in non-pressurised, hand-actuated spray pumps. Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW formulations but with an additional polymerisation stage 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 therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of Formula (I) and they may be used for seed treatment. A compound of Formula (I) may also be formulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound. 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 uptake or mobility of a compound of Formula (I). Such additives include surface active agents (SAAs), spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), modified plant oils such as methylated rape seed oil (MRSO), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of a compound of Formula (I). Wetting agents, dispersing agents and emulsifying agents may be SAAs of the cationic, anionic, amphoteric or non-ionic type. Suitable SAAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts. Suitable anionic SAAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di-isopropyl- and tri-isopropyl-naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulphosuccinamates, paraffin or olefine sulphonates, taurates, lignosulphonates and phosphates / sulphates of tristyrylphenols. Suitable SAAs of the amphoteric type include betaines, propionates and glycinates. Suitable SAAs of the non-ionic type 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 (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); lecithins and sorbitans and esters thereof, alkyl polyglycosides and tristyrylphenols. Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose) and swelling clays (such as bentonite or attapulgite). The compounds of 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), aclonifen, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, benquitrione, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, bilanafos, bipyrazone, bispyribac-sodium, bixlozone, bromacil, bromoxynil, butachlor, butafenacil, carfentrazone (including carfentrazone- ethyl), cloransulam (including cloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotoluron, chlorsulfuron, cinmethylin, clacyfos, clethodim, clodinafop (including clodinafop-propargyl), clomazone, clopyralid, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cyhalofop (including cyhalofop-butyl), 2,4-D (including the choline salt and 2-ethylhexyl ester thereof), 2,4-DB, desmedipham, dicamba (including the aluminium, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts thereof) diclosulam, diflufenican, diflufenzopyr, dimethachlor, dimethenamid-P, dioxopyritrione, diquat dibromide, diuron, epyrifenacil, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flazasulfuron, florasulam, florpyrauxifen (including florpyrauxifen-benzyl), fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), flufenacet, flumetsulam, flumioxazin, fluometuron,fomesafen, flupyrsulfuron (including flupyrsulfuron-methyl-sodium), fluroxypyr (including fluroxypyr-meptyl), fomesafen, foramsulfuron, glufosinate (including L-glufosinate and the ammonium salts of both), glyphosate (including the diammonium, isopropylammonium and potassium salts thereof), halauxifen (including halauxifen-methyl), haloxyfop (including haloxyfop-methyl), hexazinone, hydantocidin, imazamox (including R-imazamox), imazapic, imazapyr, imazethapyr, indaziflam, iodosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron (including iofensulfuron-sodium), ioxynil, isoproturon, isoxaflutole, lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron-methyl), mesotrione, metamitron, metazachlor, methiozolin, metolachlor, metosulam, metribuzin, metsulfuron, napropamide, nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, phenmedipham, picloram, pinoxaden, pretilachlor, primisulfuron-methyl, prometryne, propanil, propaquizafop, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen-ethyl), pyrasulfotole, pyridate, pyriftalid, pyrimisulfan, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quizalofop (including quizalofop-P-ethyl and quizalofop-P-tefuryl), rimisoxafen, rimsulfuron, saflufenacil, sethoxydim, simazine, S-metalochlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn, tetflupyrolimet, thiencarbazone, thifensulfuron, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, tribenuron (including tribenuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), trifludimoxazin, trifluralin, triflusulfuron, tripyrasulfone, 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4- trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole- 5-carboxylic acid ethyl ester,4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2- pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]- imidazolidine-2-one, 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]- imidazolidin-2-one, 4-hydroxy-1-methyl-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-methyl-imidazolidin-2- one, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (including agrochemically acceptable esters thereof, for example, methyl 4-amino-3- chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, prop-2-ynyl 4-amino- 3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate and cyanomethyl 4- amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate), 3-ethyl- sulfanyl-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, 3-(isopropylsulfonyl- methyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]- pyridine-8-carboxamide, 3-(ethylsulfonylmethyl)-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-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy]acetate,6- chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one, tetrahydro- furan-2-ylmethyl(2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]-propanoate, (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoic acid, tetrahydrofuran- 2-ylmethyl2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoate, 2-[(4-amino- 3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoic acid, 2-fluoro-N-(5-methyl-1,3,4- oxadiazol-2-yl)-3-[(R)-propylsulfinyl]-4-(trifluoromethyl)benzamide, 2-fluoro-N-(5- methyl-1,3,4-oxadiazol-2-yl)-3-propylsulfinyl-4-(trifluoromethyl)benzamide, (2- fluorophenyl)methyl6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)- pyrimidine-4-carboxylate, 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)- pyrimidine-4-carboxylic acid, 3-(3-chlorophenyl)-6-(5-hydroxy-1,3-dimethyl-pyrazole- 4-carbonyl)-1,5-dimethyl-quinazoline-2,4-dione and [4-[3-(3-chlorophenyl)-1,5- dimethyl-2,4-dioxo-quinazoline-6-carbonyl]-2,5-dimethyl-pyrazol-3-yl]N,N- diethylcarbamate. The mixing partners of the compound of Formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, Sixteenth Edition, British Crop Protection Council, 2012. 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. The mixing ratio of the compound of Formula (I) to the mixing partner is preferably from 1: 100 to 1000:1. The mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient" relates to the respective mixture of compound of Formula (I) with the mixing partner). The compounds or mixtures of the present invention can also be used in combination with one or more herbicide safeners. Examples of such safeners include benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen and oxabetrinil. Particularly preferred are mixtures of a compound of Formula (I) with cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and/or metcamifen. The safeners of the compound of Formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 16^th Edition (BCPC), 2012. The reference to cloquintocet-mexyl also applies to a lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salt thereof as disclosed in WO 02/34048. Preferably the mixing ratio of compound of Formula (I) to safener is from 100:1 to 1:10, especially from 20:1 to 1:1. The present invention still further provides a method of controlling weeds at a locus said method comprising application to the locus of a weed controlling amount of a composition comprising a compound of Formula (I). Moreover, the present invention may further provide a method of selectively controlling weeds at a locus comprising crop plants and weeds, wherein the method comprises application to the locus of a weed controlling amount of a composition according to the present invention. ‘Controlling’ means killing, reducing or retarding growth or preventing or reducing germination. It is noted that the compounds of the present invention show a much-improved selectivity compared to know, structurally similar compounds. Generally the plants to be controlled are unwanted plants (weeds). ‘Locus’ means the area in which the plants are growing or will grow. The application may be applied to the locus pre-emergence and/or postemergence of the crop plant. Some crop plants may be inherently tolerant to herbicidal effects of compounds of Formula (I). Preferred crop plants include maize, wheat, barley soybean and rice. The rates of application of compounds of Formula I may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post- emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the weed(s) to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. The compounds of Formula I according to the invention are generally applied at a rate of from 10 to 2500 g/ha, especially from 25 to 1000 g/ha, more especially from 25 to 250 g/ha. The application is generally made by spraying the composition, typically by tractor mounted sprayer for large areas, but other methods such as dusting (for powders), drip or drench can also be used. Crop plants are to be understood as also including those crop plants which have been rendered tolerant to other herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO-, HPPD-, -PDS and ACCase-inhibitors) by conventional methods of breeding or by genetic engineering. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant to herbicides by genetic engineering 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. Crop plants are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle). Examples of Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds). The Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria. Examples of toxins, or transgenic plants able to synthesise such toxins, are described in EP-A-451878, EP-A-374753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examples of transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut ^ (maize), Yield Gard ^ (maize), NuCOTIN33B ^ (cotton), Bollgard ^ (cotton), NewLeaf ^ (potatoes), NatureGard ^ and Protexcta ^. Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding (“stacked” transgenic events). For example, seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate. Crop plants are also to be understood to include those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour). The compositions can be used to control unwanted plants (collectively, ‘weeds’). The weeds to be controlled may be both 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. In a further aspect of the present invention there is provided the use of a compound of Formula (I) as defined herein as a herbicide. Processes for preparation of compounds of Formula (I) Processes for preparation of compounds, e.g. a compound of formula (I) (which optionally can be an agrochemically acceptable salt thereof), are now described, and form further aspects of the present invention. As shown in scheme 1 a compound of Formula (I) can be prepared by nucleophilic substitution by heating an aryl imidazole of Formula 2 in a suitable solvent, such as sulfolane or N,N-dimethylformamide in the presence of a base such as potassium or caesium carbonate with a compound of Formula 3 (where LG is halogen). The reaction is typically conducted at temperature ranging from 50 to 110^oC. Conditions for the formation of imidazole compounds of Formula 2 are well documented in the literature (see for example Journal of Medicinal Chemistry, 2000, 43, 2165 and Synthetic Communications, 2020, 50, 700). Scheme 1

Alternatively, as shown in scheme 2, chemistry based on “C-H activation” can be used to prepare compounds of Formula (I). A compound of Formula 4 can be first be converted to a compound of Formula 6 by nucleophilic substitution by heating in a suitable solvent, such as acetonitrile or N,N-dimethylformamide in the presence of a base such as potassium or caesium carbonate with a compound of Formula 5 (where LG is halogen). The resulting alkylated imidazole of Formula 6 can then be arylated using C-H activation methods as outlined in Synlett, 2020, 31, 1015. Scheme 2

4 ₆ R ^I Compounds of Formula (I) can be further halogenated, with a suitable halogenating agent such as N-chlorosuccinimide, N-bromosuccinimide or N-iodosuccinimide in a suitable solvent such as acetonitrile (scheme 3). The halogens can then be further functionalised by methods reported in the literature (WO2020/132269, 2020) Scheme 3

Alternatively, compounds of formula I, wherein Q, R², R³ and R¹(m) are as defined in formula I above can be prepared following scheme 4. Scheme 4 R 3

1² Formula I In scheme 4 compounds of formula I can be prepared by Suzuki cross-coupling reaction between compounds of formula 12, wherein X² is a leaving group like, for example, chlorine, bromine or iodine, with compounds of formula Yb2-Q 13 wherein Q is as defined in formula I above and Yb2 can be a boron-derived functional group, such as for example B(OH)2 or B(ORb2)2 wherein Rb2 can be a C1-C4alkyl group or the two groups ORb2 can form together with the boron atom a five membered ring, as for example a pinacol boronic ester. The reaction may be catalyzed by a palladium based catalyst, for example tetrakis(triphenyl-phosphine)palladium(0), (1,1'bis(diphenylphosphino)ferrocene)dichloro-palladium-dichloromethane (1:1 complex) or chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'- amino-1,1'-biphenyl)]palladium(II) (XPhos palladacycle), in presence of a base, like sodium carbonate, tripotassium phosphate or cesium fluoride, in a solvent or a solvent mixture, like, for example dioxane, 2-methyl tetrahydrofuran, acetonitrile, N,N-dimethyl-formamide, a mixture of 1,2-dimethoxyethane and water or of dioxane/water, or of toluene/water, preferably under inert atmosphere. The reaction temperature can preferentially range from room temperature to the boiling point of the reaction mixture, or the reaction may be performed under microwave irradiation. Such Suzuki reactions are well known to those skilled in the art. Compounds of formula 12, can be prepared by alkylation reaction of compounds of formula 10, with compounds of formula 11, wherein LG₁ is a halogen, preferably iodine, bromine or chlorine (or a pseudo-halogen leaving group, such as a (halo)alkyl or phenyl sulfonate ester, e.g. triflate), in the presence of a base, such as sodium hydride or an alkaline earth metal hydride, carbonate (e.g. sodium carbonate, potassium carbonate or cesium carbonate) or hydroxide, optionally in the presence of potassium iodide in an inert solvent such as tetrahydrofuran, dioxane, water, N,N- dimethylformamide DMF, sulfolane, N,N-dimethylacetamide or acetonitrile and the like, at temperatures between 0 and 120°C, by procedures well known to those skilled in the art. Compounds of formula 10 can be prepared by protecting group deprotection reaction from compounds of formula 9, wherein PG1 is an amino-protecting group for example acetyl, trimethylsilylethoxymethyl (SEM), tert-butyloxycarbonyl amongst others amino protecting groups. Such reactions are well known to those skilled in the art and can be carried out for example using base catalyzed or acid catalyzed such as HCl. Compounds of formula 9, can be prepared from compounds of formula 8 using halogenation reaction. Such reactions can be carried out in a two-step procedure which involved metalation using strong base such as butyl lithium, tert-butyl lithium, lithium tetramethylpiperidide, lithium diisopropylamide amongst other bases and quenching with suitably desired halogenating reagent such as molecular iodine, bromine or chlorine. Alternatively, halogenation reactions can be carried out in one step under radical conditions using halogenating reagent such as N- bromosuccinimide in the presence of a radical initiator such as azobisisobutyronitrile. Compounds of formula 8 can be prepared from compounds of formula 7 by protection group installation. Such reactions can be carried out in the presence of base such as sodium hydride, potassium carbonate, sodium carbonate, and in the presence of suitable protecting group reagents such as 2-(trimethylsilyl)ethoxymethyl chloride, acetyl chloride, di-tert-butyl dicarbonate and in the presence of solvent such as tetrahydrofuran, methanol, water, acetonitrile, dimethylformamide. A compound of formula I-1 is a compound of Formula I, wherein R² is -CF₂H, R³ is -H and Q and R¹(m) are as defined in formula I. Compounds of formula I-1 can be Scheme 5 R 17 1 (m)

prepared following scheme 5. In scheme 5 compounds of formula I-1 can be prepared by Suzuki cross-coupling reaction between compounds of formula 22, wherein X³ is a leaving group like, for example, chlorine, bromine or iodine, with compounds of formula Yb₃-Q 23 wherein Q is as defined in formula I above and Yb₃ can be a boron-derived functional group, such as for example B(OH)₂ or B(OR_b2)₂ wherein R_b2 can be a C₁-C₄alkyl group or the two groups OR_b2 can form together with the boron atom a five membered ring, as for example a pinacol boronic ester following procedure as described in scheme 4 for the conversion of compounds of formula 12 to compounds of formula I. Compounds of formula 22 can be prepared from compounds of formula 21 via fluorination reaction using fluorinating reagents such as diethylaminosulfur trifluoride or bis(2-methoxyethyl)aminosulfur trifluoride amongst others. Compounds of formula 21 can be prepared from compounds of formula 20 via oxidation reaction using oxidizing reagents such as MnO2, SO3.pyridine, pyridinium dichromate or pyridinium chlorochromate amongst other alcohol oxidizing reagents. Alternatively compounds of formula 21 can be prepared following scheme 6. Scheme 6

In can of formula 30 with compounds of formula 26 following procedure analogous to as described in scheme 4 for the conversion of compounds of formula 10 to compounds of formula 12. Compounds of formula 30 can be prepared from compounds of formula 29 via halogenation followed by N-deprotection reaction. Halogenation reactions can be carried out in one step under radical conditions using halogenating reagent such as N-bromosuccinimide in the presence of a radical initiator such as azobisisobutyronitrile. Deprotection reactions are well known to those skilled in the art and can be carried out for example using base catalysed or acid catalysed such as HCl. Compounds of formula 29 can be prepared from compound of formula 28 by protection group installation. Such reactions can be carried out in the presence of base such as sodium hydride, potassium carbonate, sodium carbonate, and in the presence of suitable protecting group reagents such as 2-(trimethylsilyl)ethoxymethyl chloride, acetyl chloride, di-tert-butyl dicarbonate and in the presence of solvent such as tetrahydrofuran, methanol, water, acetonitrile, dimethylformamide. Compounds of formula 20 can be prepared from compounds of formula 19, wherein R²¹ is C1-C6alkyl via reduction reactions using reducing agents such as lithium aluminium hydride or diisobutylaluminium hydride. Compounds of formula 19 can be prepared by reacting compounds of formula 17 with compounds of formula 18, wherein LG₂ is a halogen, preferably iodine, bromine or chlorine (or a pseudo- halogen leaving group, such as a (halo)alkyl or phenyl sulfonate ester, e.g. triflate), in the presence of a base, such as sodium hydride or an alkaline earth metal hydride, carbonate (e.g. sodium carbonate, potassium carbonate or cesium carbonate) or hydroxide, optionally in the presence of potassium iodide in an inert solvent such as tetrahydrofuran, dioxane, water, N,N-dimethylformamide DMF, sulfolane, N,N- dimethylacetamide or acetonitrile and the like, at temperatures between 0 and 120°C, by procedures well known to those skilled in the art. Compounds of formula 17 can be prepared from compounds of formula 14 in three steps (scheme 5) following procedure analogous to as described in scheme 4 for the conversion of compounds of formula 7 to compounds of formula 10. Alternatively compounds of formula I-1 can be prepared following scheme 7. Scheme 7 L^G _{3 N} 1 (m) H

In scheme 7 compounds of formula I-1 can be prepared from compounds of formula 27 via fluorination reaction using fluorinating reagents such as diethylaminosulfur trifluoride or bis(2-methoxyethyl)aminosulfur trifluoride amongst others. Compounds of formula 27 can be prepared by reacting compounds of formula 25 with compounds of formula 26, wherein LG3 is a halogen, preferably iodine, bromine or chlorine (or a pseudo-halogen leaving group, such as a (halo)alkyl or phenyl sulfonate ester, e.g. triflate), in the presence of a base, such as sodium hydride or an alkaline earth metal hydride, carbonate (e.g. sodium carbonate, potassium carbonate or cesium carbonate) or hydroxide, optionally in the presence of potassium iodide in an inert solvent such as tetrahydrofuran, dioxane, water, N,N-dimethylformamide DMF, sulfolane, N,N-dimethylacetamide or acetonitrile and the like, at temperatures between 0 and 120°C, by procedures well known to those skilled in the art. Alternatively compounds of formula 27 can be prepared under Mitsunobu reaction conditions from compounds of formula 25 and compounds of formula 26b. Compounds of formula 25 can be prepared from compounds of formula 24 via oxidation reaction using oxidizing agents such as MnO2, SO3.pyridine, pyridinium dichromate or pyridinium chlorochromate amongst other alcohol oxidizing reagents. Compounds of formula 24 can be prepared following procedure reported in literature for example in J. Med. Chem.1995, 38, 2251-2255. Alternatively compounds of formula 27 can be prepared following scheme 8. In scheme 8, compound of formula 27 can be prepared by reacting compounds of formula 25 with compounds of formula 26, following procedure analogous to as described in scheme 4 for the conversion of compounds of formula 10 to compounds of formula 12. Scheme 8

Compound of formula 25 can be prepared by reacting compound of formula 32 with a suitable reducing agent such as diisobutyl aluminium hydride. Compound of formula 32 can be prepared by reacting compound of formula 31 with ammonium hydroxide or similar other ammonia surrogates to transform the trifluoromethyl group to a cyano group. Such reactions are well documented in the literature (see for example Matthews, D. P.; Whitten, J. P.; McCarthy, J. R. J. Org. Chem. 1986, 51, 3228). Synthesis of imidazole compounds of Formula 31 are well documented in the literature (see for example Journal of Medicinal Chemistry, 2000, 43, 2165 and Synthetic Communications, 2020, 50, 700).

The following non-limiting examples provide specific synthesis methods for representative compounds of the present invention, as referred to in Table 1 below. Example 1: Preparation of 2-chloro-5-[1-[(3,5-difluoro-2-pyridyl)methyl]-4- (trifluoromethyl)imidazol-2-yl]-3-fluoro-pyridine 1.001:

1.001 Step 1: Preparation of 6-chloro-5-fluoro-pyridine-3-carbaldehyde I1:

(I1) To a solution of 5-bromo-2-chloro-3-fluoropyridine (11.5 g, 54.7 mmol), in THF (100 mL) at 0 °C under N₂ was added Isopropylmagnesium chloride lithium chloride complex solution/ Turbo Grignard – 1.3M (50 mL, 65 mmol) dropwise maintaining an internal reaction temperature of 5 °C. The solution was stirred for 1h at 0 °C. To the reaction was added DMF (8.02 g, 110 mmol) dropwise maintaining an internal reaction temperature below 10 °C. The reaction was stirred for 20 minutes and sat. NH4Cl (10 mL) was added. The reaction was then diluted with ethyl acetate (150 mL) and sat. Brine (100 mL). The phases were separated and the aqueous extracted with ethyl acetate (3 x 50 mL). The organics were combined and then concentrated onto granulated celite. The crude product was purified by flash chromatography on silica gel using a gradient of 0-30% Ethyl acetate in cyclohexane as eluent to give 6-chloro- 5-fluoro-pyridine-3-carbaldehyde I1 (6.21 g, 71%) as a pale pink solid.¹H NMR (400 MHz, CDCl3) δ = 10.12 (d, 1H), 8.71 (d, 1H), 7.94 (dd, 1H). Step 2 – Preparation of 2-chloro-3-fluoro-5-[4-(trifluoromethyl)-1H-imidazol-2- yl]pyridine I2: To a solution of sodium

(30 mL) was added 1,1- dibromo-3,3,3-trifluoroacetone (6.98 mL, 48.7 mmol) giving a turbid solution. The reaction was heated to 100 °C for 30 minutes then cooled to room temperature. This crude reaction mixture was then added dropwise to a solution of 6-chloro-5-fluoro- pyridine-3-carbaldehyde I1 (6.21 g, 38.9 mmol) as a solution in methanol (100 mL) and aqueous ammonia 35% (30.00 mL, 260 mmol) dropwise with cooling in an ice- bath. The reaction mixture was then stirred at room temperature for 16h. The volatiles were removed by concentration under vacuum and Ethyl acetate (100 mL), water (50 mL) and sat. Brine (50 mL) were added. The phases were separated, and the aqueous phase was extracted with Ethyl acetate (3 x 50 mL). The organics were combined and washed with sat. Brine (100 mL). The organics were then concentrated onto granulated celite. The crude product was purified by flash chromatography on silica gel using a gradient of 0-60% Ethyl acetate in cyclohexane as eluent to give 2-chloro-3-fluoro-5-[4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine I2 (6.97g, 65%) as a pale yellow solid.¹H NMR (400 MHz, CDCl3) δ = 8.77 (d, 1H), 8.21 (dd, 1H), 7.77 (q, 1H) Step 3 – Preparation of 2-chloro-5-[1-[(3,5-difluoro-2-pyridyl)methyl]-4- (trifluoromethyl)imidazol-2-yl]-3-fluoro-pyridine (1.001):

(1.001) To a stirred suspension of 2-chloro-3-fluoro-5-[4-(trifluoromethyl)-1H-imidazol-2- yl]pyridine I2 (100 mg, 0.36 mmol), potassium iodide (12 mg, 0.072 mmol) and potassium carbonate (121 mg, 0.88 mmol) in acetonitrile (20 mL) and water (0.2 mL) was added 2-(chloromethyl)-3,5-difluoro-pyridine (71 mg, 0.43mmol) in a single portion. The reaction was then heated to 70 °C under N₂ for 1.5h. The reaction was cooled to room temperature and quenched with sat. Brine (10 mL), water (10 mL) and ethyl acetate were added. The phases were separated, and the aqueous phase extracted with ethyl acetate (3 x 10 mL). The organics were combined and concentrated onto granulated celite. The crude product was purified by flash chromatography on silica gel using a gradient of 0-40% Ethyl acetate in cyclohexane as eluent to give 2-chloro-5-[1-[(3,5-difluoro-2-pyridyl)methyl]-4- (trifluoromethyl)imidazol-2-yl]-3-fluoro-pyridine (1.001) (116 mg, 78%) as a pale yellow solid.¹H NMR (400 MHz, CDCl₃) δ = 8.67 (d, 1H), 8.38 (d, 1H), 8.05 (dd, 1H), 7.48 (d, 1H), 7.33 (m, 1H), 5.34 (d, 2H) Example 2: Preparation of 5-chloro-2-[[4-(difluoromethyl)-2-[4- (trifluoromethyl)phenyl]imidazol-1-yl]methyl]-3-fluoro-pyridine 1.005:

(1.005) Step 1 – Preparation of [2-[4-(trifluoromethyl)phenyl]-1H-imidazol-4-yl]methanol I3:

(I3) To a round bottom flask was added 4-(trifluoromethyl)benzamidine hydrochloride (10.03 g, 42.4 mmol), 1,3-dihydroxyacetone dimer (7.85 g, 42.3 mmol), ammonium chloride (9.06 g, 169 mmol) and aqueous ammonia 35% (210 mL) giving a yellow solution. The reaction mixture was heated to 45 °C for 48 h. The reaction mixture was extracted with ethyl acetate (3 x 100 mL). The organics were combined and then concentrated onto granulated celite. The crude product was purified by flash chromatography on silica gel using a gradient of 40-80% 3:1 - ethyl acetate:ethanol in cyclohexane as eluent to give [2-[4-(trifluoromethyl)phenyl]-1H-imidazol-4- yl]methanol I3 (4.67 g, 43%). ¹H NMR (400 MHz, DMSO-d6) δ = 12.88 - 12.55 (m, 1H), 8.13 (br s, 2H), 7.80 (d, 2H), 7.24 - 6.88 (m, 1H), 5.26 - 4.87 (m, 1H), 4.55 - 4.37 (m, 2H). Step 2 – Preparation of 2-[4-(trifluoromethyl)phenyl]-1H-imidazole-4- carbaldehyde I4:

To a solution of [2-[4-(trifluoromethyl)phenyl]-1H-imidazol-4-yl]methanol I3 (4.67 g, 18.3 mmol) in ethyl acetate (185 mL) was added MnO₂ (16.11 g, 183 mmol) giving a black suspension. The reaction was stirred at room temperature for 112 h. The reaction mixture was filtered through a pad of Kieselguhr and the pad washed with Ethyl acetate (3 x 100 mL). The yellow filtrate was concentrated under vacuum to give 2-[4-(trifluoromethyl)phenyl]-1H-imidazole-4-carbaldehyde I4 (3.77g, 82%). ¹H NMR (400 MHz, DMSO) δ = 13.72 (br s, 1H), 9.81 (s, 1H), 8.27 (d, 2H), 8.20 (s, 1H), 7.89 (d, 2H). Step 3 – Preparation of 1-[(5-chloro-3-fluoro-2-pyridyl)methyl]-2-[4- (trifluoromethyl)phenyl]imidazole-4-carbaldehyde I5:

To a solution of 2-[4- - 4-carbaldehyde I4 (405 mg, 1.60 mmol), (5-chloro-3-fluoropyridin-2-yl)methanol (408 mg, 2.40 mmol) and triphenylphosphine (851 mg, 3.18 mmol) in 2-methyltetrahydrofuran (13 mL) at 0 °C was added diisopropyl azodicarboxylate (0.64 mL, 3.20 mmol) dropwise. The reaction was stirred rapidly at 0 °C for 2h, warmed to room temperature and quenched with methanol (5 mL). The reaction mixture was concentrated onto granulated celite. The crude product was purified by reverse phase flash chromatography on C-18 silica gel using a gradient of 50-100% acetonitrile in water (with 0.1% formic acid additive) as eluent to give 1-[(5-chloro-3-fluoro-2- pyridyl)methyl]-2-[4-(trifluoromethyl)phenyl]imidazole-4-carbaldehyde I5 (118 mg, 17%).¹H NMR (400 MHz, CDCl₃) δ = 9.93 (s, 1H), 8.41 (dd, 1H), 7.86 (d, 2H), 7.81 (s, 1H), 7.76 (d, 2H), 7.53 (dd, 1H), 5.37 (d, 2H). Step 4 – Preparation of 5-chloro-2-[[4-(difluoromethyl)-2-[4- (trifluoromethyl)phenyl]imidazol-1-yl]methyl]-3-fluoro-pyridine (1.005):

(1.005) To a solution of 1-[(5-chloro-3-fluoro-2-pyridyl)methyl]-2-[4- (trifluoromethyl)phenyl]imidazole-4-carbaldehyde I5 (118 mg, 0.277 mmol) in dichloromethane (5 mL) was added diethylaminosulfur trifluoride (0.3 mL, 2.00 mmol) dropwise. The reaction was stirred for 16h and a further aliquot of diethylaminosulfur trifluoride (0.08 mL, 0.60 mmol) was added to the reaction mixture. The reaction mixture was stirred for 3h and quenched with sat. sodium bicarbonate (15 mL). The phases were separated, and the aqueous phase extracted with Ethyl acetate (3 x 10 mL). The organics were combined and concentrated onto granulated celite. The crude product was purified by flash chromatography on silica gel using a gradient of 0-50% Ethyl acetate in cyclohexane as eluent to give 5-chloro-2-[[4-(difluoromethyl)- 2-[4-(trifluoromethyl)phenyl]imidazol-1-yl]methyl]-3-fluoro-pyridine 1.005 (52 mg, 44%).¹H NMR (400 MHz, CDCl₃) δ = 8.42 (m, 1H), 7.85 (d, 2H), 7.74 (d, 2H), 7.52 (dd, 1H), 7.35 (t, 1H), 6.70 (br t, 1H), 5.32 (d, 2H). Example 3: Preparation of 5-chloro-2-[1-[[6-(difluoromethoxy)-2-pyridyl]methyl]- 4-(trifluoromethyl)imidazol-2-yl]pyrimidine 1.020:

Step 1 – Preparation of 2-(difluoromethoxy)-6-[[4-(trifluoromethyl)imidazol-1-

(I6) To a suspension of 4-(trifluoromethyl)imidazole (66 mg, 0.49 mmol) and K₂CO₃ (134 mg, 0.97 mmol) in sulfolane (1.32 mL) was added 2-(chloromethyl)-6- (difluoromethoxy)pyridine (99 mg, 0.49 mmol) and the reaction mixture stirred rapidly at room temperature under N₂ for 3h. The reaction was then heated to 50 °C under N₂ for 1.5h. The reaction was cooled to room temperature and quenched with water (10 mL). Methyl tert-butyl ether (10 mL) was added, and the phases were separated. The aqueous phase was extracted with methyl tert-butyl ether (3 x 20 mL), the organics combined and concentrated onto granulated celite. The crude product was purified by flash chromatography on silica gel using a gradient of 0-100% ethyl acetate in cyclohexane and product containing fractions after concentration were further purified by reverse phase flash chromatography on C-18 silica gel using a gradient of 30-100% acetonitrile in water (with 0.1% formic acid additive) as eluent to give 2-(difluoromethoxy)-6-[[4-(trifluoromethyl)imidazol-1-yl]methyl]pyridine I6 (118 mg, 17%) as a colourless oil. ¹H NMR (400 MHz, CDCl₃) δ = 7.76 (dd, 1H), 7.68 - 7.62 (m, 1H), 7.35 - 7.33 (m, 1H), 7.35 (t, 1H), 6.91 - 6.86 (m, 2H), 5.17 (s, 2H) Step 2 – Preparation of 5-chloro-2-[1-[[6-(difluoromethoxy)-2-pyridyl]methyl]-4- (trifluoromethyl)imidazol-2-yl]pyrimidine 1.020:

To a 0.5-2 mL microwave vial containing CuI (7 mg, 0.38 mmo), Pd(OAc)2 (0.2 mg, 0.009 mmol), triphenylphosphine (0.5 mg, 0.019 mmol) was added a solution of 2- (difluoromethoxy)-6-[[4-(trifluoromethyl)imidazol-1-yl]methyl]pyridine I6 (55 mg, 0.19 mmol) in dioxane (1.5 mL) under N2. The reaction was heated to 140 °C under microwave irradiation for 4h. The reaction was cooled to room temperature and concentrated onto granulated celite. The crude product was purified by flash chromatography on silica gel using a gradient of 0-100% Ethyl acetate in cyclohexane and product containing fractions (after concentration) were further purified by reverse phase flash chromatography on C-18 silica gel using a gradient of 10-100% acetonitrile in water (with 0.1% formic acid additive) as eluent to give 5- chloro-2-[1-[[6-(difluoromethoxy)-2-pyridyl]methyl]-4-(trifluoromethyl)imidazol-2- yl]pyrimidine 1.020 (6 mg, 8%).¹H NMR (400 MHz, chloroform) δ = 8.76 (s, 2H), 7.71 - 7.63 (m, 1H), 7.55 - 7.47 (m, 1H), 0.00 (t, 1H), 6.82 (dd, 2H), 5.91 (s, 2H). Example 4: Preparation of 3-chloro-5-[1-[(5-chloro-3-fluoro-2-pyridyl)methyl]-4- (difluoromethyl)imidazol-2-yl]-2-fluoro-pyridine (1.023):

(1.023) Step 1 – Preparation of 2-bromo-1-[(5-chloro-3-fluoro-2- pyridyl)methyl]imidazole-4-carbaldehyde (I7):

A solution of 5-chloro-2-(chloromethyl)-3-fluoro-pyridine (1.34 g, 7.05 mmol) in acetonitrile (35 mL) in a 250 mL round bottomed flask was treated with 2-bromo-1H- imidazole-4-carbaldehyde; hydrobromide (2.21 g, 8.64 mmol), potassium carbonate (2.94 g, 21.3 mmol), potassium iodide (261 mg, 1.57 mmol) and water (1.8 mL). The resulting mixture was warmed to 70 ^oC and was allowed to stir for 1 h. The reaction mixture was allowed to cool to room temperature before being diluted with water (80 mL) and extracted with ethyl acetate (2 x 80 mL). The combined organics were washed with brine and concentrated in vacuo to get the crude. The residues were loaded onto celite and subjected to silica gel column chromatography using 0-60% ethyl acetate in cyclohexane. Upon concentration of the fractions, 2-bromo-1-[(5- chloro-3-fluoro-2-pyridyl)methyl]imidazole-4-carbaldehyde I7 (1.75 g, 75%) was obtained as beige solid. ¹H NMR (400 MHz, CDCl₃) δ = 9.79 (s, 1H), 8.40-8.38 (m, 1H), 7.78 (s, 1H), 7.54 (dd, 1H), 5.33 (d, 2H). Step 2- Preparation of 2-[[2-bromo-4-(difluoromethyl)imidazol-1-yl]methyl]-5- chloro-3-fluoro-pyridine (I7a):

A solution of 2-bromo-1-[(5-chloro-3-fluoro-2-pyridyl)methyl]imidazole-4- carbaldehyde I7 (1.754 g, 5.231 mmol) in dichloromethane (20 mL, 312.0 mmol) in a 50 mL round bottomed flask was cooled to 0 ^oC and treated with diethylamino sulfur trifluoride (3.5 mL, 26 mmol). The resulting reaction mixture was allowed to stir at room temperature for 22.5 hours and then diluted with aqueous sodium carbonate (80 mL) and extracted with dichloromethane (2 x 30 mL). The combined organics were passed through a hydrophobic frit and concentrated in vacuo. The residues were loaded onto celite and subjected to column chromatography (40 g RediSep column, 0-30% ethyl acetate in cyclohexane). The fractions forming the major peak of interest were combined and concentrated in vacuo, yielding 2-[[2-bromo-4- (difluoromethyl)imidazol-1-yl]methyl]-5-chloro-3-fluoro-pyridine I7a (1.032 g, 55% yield).¹H NMR (400 MHz, chloroform) δ = 8.42 - 8.38 (m, 1H), 7.53 (dd, 1H), 7.35 (t, 1H), 6.59 (t, 1H), 5.29 (d, 2H). Step 3 – Preparation of 3-chloro-2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)pyridine (I8):

(I8) A mixture of 5-bromo-3-chloro-2-fluoropyridine (1.02 g, 4.85 mmol), bis(pinacolato)diboron (1.50 g, 5.85 mmol), 1,1'-bis(diphenylphosphino)ferrocene- palladium(ii)dichloride dichloromethane complex (393 mg, 0.467 mmol) and potassium acetate (991 mg, 9.90 mmol) in a 100 mL round bottomed flask was placed under an atmosphere of nitrogen. The mixture was treated with 2- methyltetrahydrofuran (16 mL), warmed to 80 ^oC and was allowed to stir for 1 h. After this time, the reaction mixture was allowed to cool to room temperature before being concentrated directly onto celite and subjected to column chromatography using 0- 20% ethyl acetate in cyclohexane. Upon concentration of the fractions, 3-chloro-2- fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine I8 (578 mg, 37%) was obtained as a white solid. ¹H NMR (400 MHz, CDCl₃) δ = 8.45 - 8.42 (m, 1H), 8.16 (dd, 1H), 1.35 (s, 12H). Step 4 – Preparation of 3-chloro-5-[1-[(5-chloro-3-fluoro-2-pyridyl)methyl]-4- (difluoromethyl)imidazol-2-yl]-2-fluoro-pyridine (1.023):

(1.023) A solution of 2-[[2-bromo-4-(difluoromethyl)imidazol-1-yl]methyl]-5-chloro-3-fluoro- pyridine (I7a, 350 mg, 0.97 mmol) in 2-methyltetrahydrofuran (4.0 mL) in a 50 mL round bottomed flask was placed under an atmosphere of nitrogen. The mixture was treated with 3-chloro-2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (I8, 409 mg, 1.27 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium(ii)dichloride dichloromethane complex (98 mg, 0.116 mmol) and potassium phosphate tribasic (2.4 mL, 1.0 M in water). The reaction vessel was evacuated and back-filled with nitrogen three times. The mixture was then warmed to 70 ^oC and was allowed to stir for 1 h. The reaction mixture was allowed to cool to room temperature before being diluted with water (30 mL) and extracted with ethyl acetate (2 x 30 mL). The combined organics were concentrated in vacuo. The residues were loaded onto celite and subjected to silica gel column chromatography using 0-40% ethyl acetate in cyclohexane. The fractions forming the major peak of interest were combined and concentrated in vacuo to get the desired product with minor impurities. This was further purified by reverse phase flash chromatography on C-18 silica gel using a gradient of 40-100% acetonitrile in water (with 0.1% formic acid additive) as eluent to give 3-chloro-5-[1-[(5-chloro-3-fluoro-2-pyridyl)methyl]-4-(difluoromethyl)imidazol-2- yl]-2-fluoro-pyridine 1.023.¹H NMR (400 MHz, CDCl₃) δ = 8.53 - 8.50 (m, 1H), 8.44 - 8.41 (m, 1H), 8.32 (dd, 1H), 7.56 (dd, 1H), 7.36 (t, 1H), 6.68 (t, 1H), 5.31 (d, 2H). Example 5: Preparation of 3-chloro-5-[5-chloro-1-[(5-chloro-3-fluoro-2- pyridyl)methyl]-4-(difluoromethyl)imidazol-2-yl]-2-fluoro-pyridine (1.022):

(1.022) A solution of 3-chloro-5-[1-[(5-chloro-3-fluoro-2-pyridyl)methyl]-4- (difluoromethyl)imidazol-2-yl]-2-fluoro-pyridine (1.023, 133 mg, 0.32 mmol) in acetonitrile (1.6 mL) in a 25 mL round bottomed flask was placed under an atmosphere of nitrogen, treated with N-chlorosuccinimide (55 mg, 0.40 mmol) and warmed to 80 ^oC. The resulting mixture was allowed to stir for 2 h. The reaction mixture was slowly added to stirring water (~40 mL) upon which a precipitate appears. The solids were collected by filtration, washed with water and cyclohexane and then dried to give 3-chloro-5-[5-chloro-1-[(5-chloro-3-fluoro-2-pyridyl)methyl]-4- (difluoromethyl)imidazol-2-yl]-2-fluoro-pyridine 1.022.¹H NMR (400 MHz, CDCl₃) δ = 8.46 - 8.42 (m, 1H), 8.40 - 8.35 (m, 1H), 8.31 (dd, 1H), 7.55 (dd, 1H), 6.70 (t, 1H), 5.33 - 5.30 (m, 2H). Example 6: Preparation of 3-chloro-2-[[2-(6-chloro-3-pyridyl)-4- (difluoromethyl)imidazol-1-yl]methyl]-5-fluoro-pyridine (1.034):

(1.034) Step 1 – Preparation of 2-chloro-5-[4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (I9):

To a 100 mL flask equipped with a reflux condenser were added sodium acetate (2.20 g, 26.49 mmol), water (7.5 mL) and 1,1-dibromo-3,3,3-trifluoroacetone (3.61 g, 12.72 mmol), resulting a turbid suspension. The reaction mixture was heated to 100 °C for 30 minutes. The reaction mixture was cooled to room temperature. To this solution was added, 6-chloropyridine-3-carbaldehyde (1.5 g, 10.60 mmol) in methanol (30.00 mL), followed by aqueous ammonia (7.50 mL, 66 mmol) slowly and stirred at room temperature for 16 h. The reaction mixture was extracted with ethyl acetate (3 × 200 mL) and the combined organic layer was washed with saturated bicarbonate solution (100 ml) and then with brine (100 mL), dried over anhydrous sodium sulphate, filtered, and concentrated to get the crude material. The crude was washed with tert-butyl methyl ether and dried to get 2-chloro-5-[4-(trifluoromethyl)- 1H-imidazol-2-yl]pyridine I9 (2.2 g, 84%) as yellow solid.¹H NMR (400 MHz, DMSO- d6) δ = 13.5 (br s, 1H), 8.98 (d, 1 H), 8.36 (dd, 1 H), 8.04 (s, 1 H), 7.66 (d, 1 H). Step 2 – Preparation of 2-(6-chloro-3-pyridyl)-1H-imidazole-4-carbonitrile (I10):

(I10) To a three necked flask was added 2-chloro-5-[4-(trifluoromethyl)-1H-imidazol-2- yl]pyridine (I9, 9.5 g, 38 mmol), methanol (48 mL) and aqueous ammonia (92 mL, 580 mmol). The reaction mixture was stirred at 70 °C for 6 h. The reaction mixture was cooled to room temperature and concentrated to get the crude material. The crude was purified by silica gel column chromatography using ethyl acetate/cyclohexane as eluents to afford 2-(6-chloro-3-pyridyl)-1H-imidazole-4- carbonitrile I10 (6 g, 76%). ¹H NMR (400 MHz, METHANOL-d4) δ = 8.90 (d, 1 H), 8.30 (dd, 1 H), 8.05 (s, 1 H), 7.61 (d, 1 H). Step 3 – Preparation of 2-(6-chloro-3-pyridyl)-1H-imidazole-4-carbaldehyde (I11):

To a stirred solution of 2-(6-chloro-3-pyridyl)-1H-imidazole-4-carbonitrile (I10, 0.8 g, 3.91 mmol) in dry tetrahydrofuran (16 mL) at -78°C was added diisobutylaluminium hydride (1.0 mol/L) in toluene (6.7 g, 7.81 mmol) dropwise and stirred at the same temperature for 1 h. Then the reaction mixture was allowed to warm to 0°C and stirred for additional 1 h at 0°C. The reaction mixture was quenched with 2N hydrochloric acid solution (~30 mL) and extracted with ethyl acetate (3 X 50 mL). The combined organic layer was washed well with water (50 mL), brine (50 mL), dried on sodium sulphate, filtered, and concentrated to get the crude material. The crude was purified by silica gel chromatography using 0-25% ethyl acetate/cyclohexane to afford 2-(6-chloro-3-pyridyl)-1H-imidazole-4-carbaldehyde I11 (0.3 g, 37%) as pale yellow solid. ¹H NMR (400 MHz, CDCl₃) δ = 9.74 (br s, 1 H), 9.10 (br s, 1 H), 8.38 (dd, 1 H), 7.79 (s, 1 H), 7.34 - 7.39 (m, 1 H). Step 4 – Preparation of 1-[(3-chloro-5-fluoro-2-pyridyl)methyl]-2-(6-chloro-3- pyridyl)imidazole-4-carbaldehyde (I12):

To a solution of 2-(6-chloro-3-pyridyl)-1H-imidazole-4-carbaldehyde (I11, 0.28 g, 1.21 mmol) in acetonitrile (2.8 mL) was added potassium carbonate (0.33 g, 2.42 mmol), 3-chloro-2-(chloromethyl)-5-fluoro-pyridine (0.26 g, 1.45 mmol) followed by potassium iodide (0.040 g, 0.24 mmol). The reaction mixture was heated to 70°C and stirred at this temperature for 4 h. After this time, the reaction mixture was cooled to room temperature, diluted with 100 ml ice cold water, extracted with ethyl acetate (4 X 200 mL). The combined organic layer was washed with brine solution (100 mL), dried over anhydrous sodium sulphate, filtered, and concentrated to get the crude material. This was purified by silica gel column chromatography using 30% ethyl acetate/cyclohexane to afford 1-[(3-chloro-5-fluoro-2-pyridyl)methyl]-2-(6-chloro-3- pyridyl)imidazole-4-carbaldehyde I12 (0.33 g, 77%) as yellow solid. ¹H NMR (400 MHz, DMSO-d6) δ = 9.80 (s, 1 H), 8.59 (s, 1 H), 8.49 (d, 1 H), 8.26 (s, 1 H), 8.18 (br d, 1 H), 8.03 (dd, 1 H), 7.61 (d, 1 H), 5.68 (s, 2 H). Step 5 – Preparation of 3-chloro-2-[[2-(6-chloro-3-pyridyl)-4- (difluoromethyl)imidazol-1-yl]methyl]-5-fluoro-pyridine (1.034):

(1.034) To a stirred solution of 1-[(3-chloro-5-fluoro-2-pyridyl)methyl]-2-(6-chloro-3- pyridyl)imidazole-4-carbaldehyde (I12, 300 mg, 0.85 mmol) in dry dichloromethane (5 mL) at 0°C was added diethylaminosulfur trifluoride (1.1 g, 6.83 mmol) dropwise and the reaction mixture was allowed to warm up to room temperature and it was stirred for overnight. The mixture was carefully quenched on saturated sodium bicarbonate solution by adding it dropwise. Then it was extracted with ethyl acetate (3 X 50 mL) and the combined organic layer was washed well with water (50 mL) and dried over sodium sulphate, filtered, and concentrated to get the crude material. The crude material was purified by silica gel column chromatography using 15% ethyl acetate in cyclohexane. Upon concentration of the pure fractions, 3-chloro-2-[[2-(6-chloro-3- pyridyl)-4-(difluoromethyl)imidazol-1-yl]methyl]-5-fluoro-pyridine 1.034 was obtained. ¹H NMR (400 MHz, CDCl3) δ = 8.69 (d, 1 H), 8.40 (d, 1 H), 8.01 - 8.08 (m, 1 H), 7.55 - 7.60 (m, 1 H), 7.46 (d, 1 H), 7.34 (t, 1 H), 6.73 (t, 1 H), 5.40 (s, 2 H).

Example 7: Preparation of 3-chloro-2-[[5-chloro-2-(6-chloro-3-pyridyl)-4- (difluoromethyl)imidazol-1-yl]methyl]-5-fluoro-pyridine (1.035):

(1.035) To a 25 mL flask equipped with N₂ inlet was added 3-chloro-2-[[2-(6-chloro-3-pyridyl)- 4-(difluoromethyl)imidazol-1-yl]methyl]-5-fluoro-pyridine (1.034, 0.15 g, 0.4 mmol), acetonitrile (3 mL), and N-chlorosuccinimide (0.07 g, 0.52 mmol) and stirred at room temperature for 16 h. The reaction mixture was quenched with 10% sodium thiosulphate solution (100 mL) and extracted with ethyl acetate (2 X 100mL), dried over sodium sulphate, filtered, and concentrated to get the crude material. This was purified by silica gel column chromatography using 5-10% ethyl acetate/ cyclohexane to afford 3-chloro-2-[[5-chloro-2-(6-chloro-3-pyridyl)-4-(difluoromethyl)imidazol-1- yl]methyl]-5-fluoro-pyridine 1.035.¹H NMR (400 MHz, CDCl₃) δ = 8.54 (d, 1 H), 8.34 (d, 1 H), 7.93 - 7.98 (m, 1 H), 7.55 - 7.59 (m, 1 H), 7.39 - 7.43 (m, 1 H), 6.74 (t, 1 H), 5.36 (d, 2H).

TABLE 1 1 Compound STRUCTURE H NMR (400MHz, CDCl₃ unless otherwise stated) δ = 8.67 (d, 1H), 8.38 (d, 1H), 8.05 1.001 (dd, 1H), 7.48 (d, 1H), 7.33 (m, 1H), 5.34 (d, 2H) 1H NMR (500 MHz, CDCl3) δ = 8.79 1.002 (d, 1H), 8.36 (d, 1H), 8.09 (dd, 1H), 7.47 (m, 2H), 7.30 (m, 1H), 5.31 (d, 2H) δ = 8.59 (dd, 1H), 8.54 (d, 1H), 8.00 1.003 (dd, 1H), 7.74 (dd, 1H), 7.46-7.44 (m, 1H), 7.12 (dd, 1H), 5.28 (s, 2H) δ = 8.65 (d, 1H), 8.43 (dd, 1H), 8.05 1.004 (dd, 1H), 7.58 (dd, 1H), 7.49-7.46 (m, 1H), 5.34 (d, 2H) δ = 8.42 (m, 1H), 7.85 (d, 2H), 7.74 1.005 (d, 2H), 7.52 (dd, 1H), 7.35 (t, 1H), 6.70 (br t, 1H), 5.32 (d, 2H) δ = 8.77 (dd, 1H), 8.42 (dd, 1H), 8.08 1.006 (dd, 1H), 7.55 (dd, 1H), 7.49 - 7.43 (m, 2H), 5.31 (d, 2H) δ = 8.43 (dd, 1H), 7.86 (d, 2H), 7.74 1.007 (d, 2H), 7.53 (dd, 1H), 7.46 - 7.43 (m, 1H), 5.33 (d, 2H) 1H NMR (400 MHz, DMSO-d6) δ = 1.008 8.58 (d, 1H), 8.09 (d, 1H), 7.95 (dd, 1H), 7.87 (d, 2H), 7.82 (d, 2H), 7.33 (d, 1H), 5.52 (s, 2H) 1 Compound STRUCTURE H NMR (400MHz, CDCl₃ unless otherwise stated) 1H NMR (500 MHz, chloroform) δ = 1.009 8.64 (d, 1H), 7.80 (d, 2H), 7.74 (m, 1H), 7.71 (d, 2H), 7.47 (s, 1H), 7.31 (dd, 1H), 7.05 (d, 1H), 5.32 (s, 2H) 1H NMR (500 MHz, chloroform) δ = 1.010 7.89 (t, 1H), 7.72 (s, 5H), 7.45 (s, 1H), 7.23 (d, 1H), 5.36 (s, 2H) 1H NMR (500 MHz, chloroform) δ = 1.011 7.77 (d, 2H), 7.72 (d, 2H), 7.58 (m, 1H), 7.49 (d, 1H), 7.45 (s, 1H), 6.95 (d, 1H), 5.30 (s, 2H) 1H NMR (500 MHz, chloroform) δ = 1.012 8.49 (d, 1H), 7.79 (d, 2H), 7.72 (d, 2H), 7.44 (m, 2H), 7.08 (dd, 1H), 5.30 (s, 2H) 1H NMR (500 MHz, chloroform) δ = 1.013 8.80 (dd, 1H), 8.03 (dd, 1H), 7.81 (d, 2H), 7.73 (d, 2H), 7.48 - 7.44 (m, 2H), 5.53 (s, 2H) 1H NMR (500 MHz, chloroform) δ = 1.014 7.76 (d, 2H), 7.71(d, 2H), 7.68 (d, 1H), 7.45 (s, 1H), 7.33 (d, 1H), 6.91 (d, 1H), 5.29 (s, 2H) 1H NMR (500 MHz, chloroform) δ ppm 7.81 (d, 2 H) 7.70 (d, 2 H) 7.64 1.015 (t, 1 H) 7.46 (s, 1 H) 7.17 (d, 1 H) 6.81 (d, 1 H) 5.32 (s, 2 H) 2.58 (s, 3 H) 1H NMR (500 MHz, chloroform) δ ppm 8.27 (d, 1 H) 7.92 (d, 2 H) 7.74 1.016 (d, 2 H) 7.45 (s, 1 H) 6.92 (d, 1 H) 5.34 (s, 2 H) 3.96 (s, 3 H) 3.67 (s, 3 H) 1 Compound STRUCTURE H NMR (400MHz, CDCl₃ unless otherwise stated) 1H NMR (500 MHz, chloroform) δ = 1.017 8.19 (d, 1H), 7.89 (d, 2H), 7.72 (d, 2H), 7.44 (s, 1H), 7.28 (dd, 1H), 7.21 (d, 1H), 5.32 (s, 2H), 3.79 (s, 3H) 1H NMR (500 MHz, chloroform) δ = 1.018 8.53 (d, 1H), 7.78 (d, 2H), 7.71 (d, 2H), 7.45 (s, 1H), 7.32 (dd, 1H), 7.07 - 7.05 (m, 1H), 5.28 (s, 2H) δ = 8.89 (d, 1H), 8.01 (dd, 1H), 7.73 1.019 (d, 2H), 7.70 (d, 2H), 7.44 (d, 1H), 7.16 (d, 1H), 5.39 (s, 2H) δ = 8.76 (s, 2H), 7.71 - 7.63 (m, 1H), 1.020 7.55 - 7.47 (m, 1H), 7.26 (t, 1H), 6.82 (dd, 2H), 5.91 (s, 2H) δ = 7.82 - 7.67 (m, 5H), 7.44 - 7.42 1.021 (m, 1H), 7.26 (t, 1H), 6.89 (dd, 2H), 5.24 (s, 2H) δ = 8.46 - 8.42 (m, 1H), 8.40 - 8.35 1.022 (m, 1H), 8.31 (dd, 1H), 7.55 (dd, 1H), 6.70 (t, 1H), 5.33 - 5.30 (m, 2H) δ = 8.53 - 8.50 (m, 1H), 8.44 - 8.41 1.023 (m, 1H), 8.32 (dd, 1H), 7.56 (dd, 1H), 7.36 (t, 1H), 6.68 (t, 1H), 5.31 (d, 2H) δ = 8.67 (s, 1H), 8.61 (s, 1H), 8.04 1.024 (dd, 1H), 7.45 (d, 2H), 7.22 (s, 1H), 5.24 (s, 2H) 1 Compound STRUCTURE H NMR (400MHz, CDCl₃ unless otherwise stated) δ = 8.63 (d, 1H), 8.01 (dd, 1H), 1.025 7.81 (d, 1H), 7.45 (dt, 2H), 6.96 (d, 1H), 5.24 (s, 2H), δ = 8.64 (d, 1H), 8.02 (dd, 1H), 1.026 7.54 - 7.49 (m, 1H), 7.47 - 7.44 (m, 2H), 7.02 (dd, 1H), 5.24 (s, 2H) δ = 8.61 (t, 1 H), 8.44 (d, 1 H), 1.027 7.72 (dd, 1 H), 7.56 (dd, 1H), 7.33 - 7.35 (m, 1 H), 6.72 (t, 1 H), 5.34 (d, 2 H), 3.27 (q, 2 H), 1.41 (t, 3 H) δ = 9.00 (s, 1 H), 8.43 (d, 1 H), 1.028 8.29 (dd, 1 H), 7.60 (dd, 1 H), 7.43 (br s, 1 H), 6.71 (t, 1 H), 5.38 (d, 2 H), 3.53 (q, 2 H), 1.43 (t, 3 H) δ = 8.40 (d, 1 H), 7.52 - 7.60 (m, 3 1.029 H), 7.43 (d, 2 H), 7.25 - 7.28 (m, 1H), 6.71 (t, 1 H), 5.37 (s, 2 H) δ = 8.40 (d, 1 H), 7.58 - 7.63 (m, 2 1.030 H), 7.53 (dd, 1 H), 7.24 - 7.28 (t, 1 H), 7.11 - 7.17 (t, 2 H), 6.71 (t, 1 H), 5.36 (s, 2 H) δ = 8.37 (d, 1 H), 7.56 (dd, 1 H), 1.031 7.46 - 7.51 (m, 2 H), 7.36 - 7.41 (m, 2 H), 5.33 - 5.37 (m, 2 H) δ = 8.41 (d, 1 H), 7.51 - 7.60 (m, 2 1.032 H), 7.34 - 7.42 (m, 2 H), 7.21 - 7.32 (m, 1 H), 5.39 (s, 2 H) 1 Compound STRUCTURE H NMR (400MHz, CDCl₃ unless otherwise stated) δ = 8.68 (s, 1 H), 8.41 (d, 1 H), 1.033 8.02 - 8.08 (m, 1 H), 7.55 - 7.61 (m, 1 H), 7.42 - 7.48 (m, 2 H), 5.41 (s, 2H) δ = 8.69 (d, 1 H), 8.40 (d, 1 H), 1.034 8.01 - 8.08 (m, 1 H), 7.55 - 7.60 (m, 1 H), 7.46 (d, 1 H), 7.34 (t, 1 H), 6.73 (t, 1 H), 5.40 (s, 2 H) δ = 8.54 (d, 1 H), 8.34 (d, 1 H), 1.035 7.93 - 7.98 (m, 1 H), 7.55 - 7.59 (m, 1 H), 7.39 - 7.43 (m, 1H), 6.74 (t, 1H), 5.36 (d, 2 H). δ = 8.41 (d, 1 H), 7.51 - 7.58 (m, 2 1.036 H), 7.36 - 7.42 (m, 1 H), 7.21 - 7.29 (m, 2 H), 6.70 (t, 1 H), 5.38 (s, 2 H) δ = 8.37 (d, 1 H), 7.57 (dd, 1 H), 1.037 7.48 (br dd, 1 H), 7.30 (ddt, 1 H), 7.20 (dt, 1 H),6.73 (t, 1 H), 5.33 - 5.38 (m, 2 H) δ = 8.40 (d, 1 H), 7.52 - 7.60 (m, 3 1.038 H), 7.41 - 7.46 (m, 2 H), 7.36 (s, 1 H), 5.38 (s, 2 H) δ = 8.41 (d, 1 H), 7.57 - 7.65 (m, 2 1.039 H), 7.54 (dd, 1 H), 7.35 (s, 1 H), 7.15 (t, 2 H), 5.37 (s, 2 H) δ = 8.43 (d, 1 H), 7.65 (s, 1 H), 1.040 7.54 - 7.61 (m, 2 H), 7.41 - 7.46 (m, 1 H), 7.28 - 7.33 (m, 1 H), 5.32 (d, 2 H) 1 Compound STRUCTURE H NMR (400MHz, CDCl₃ unless otherwise stated) δ = 8.44 (s, 1 H), 7.63 (ddd, 1 H), 1.041 7.55 (dd, 1 H), 7.45 - 7.50 (m, 1 H), 7.42 (d, 1 H), 7.22 - 7.33 (m, 1 H), 5.31 (d, 2 H) δ = 8.39 (d, 1 H), 7.58 - 7.64 (m, 1 1042 H), 7.54 (dd, 1 H), 7.44 (ddd, 1 H), 7.20 - 7.27 (m, 1 H), 6.71 (t, 1 H), 5.29 - 5.33 (m, 2 H) δ = 8.39 (d, 1 H), 7.64 (ddd, 1 H), 1.043 7.45 - 7.52 (m, 1 H), 7.42 (s, 1 H), 7.25 -7.33 (m, 2 H), 5.32 (d, 2 H) δ = 8.40 (d, 1 H), 7.67 (br dd, 1 H), 1.044 7.65 (br dd, 1 H), 7.27 - 7.36 (m, 3 H), 6.71 (t, 1 H), 5.33 (d, 2 H) δ = 8.43 (d, 1 H), 7.61 (dd, 1 H), 1.045 7.54 (dd, 1 H), 7.44 - 7.50 (m, 1 H), 7.24 - 7.33 (m, 2 H), 6.69 (t, 1 H), 5.30 (d, 2 H) δ = 8.65 (d, 1H), 8.43 - 8.41 (m, 1.046 1H), 8.04 (dd, 1H), 7.56 (dd, 1H), 7.37 (t, 1H), 6.68 (t, 1H), 5.33 (d, 2H) δ = 8.68 (s, 1H), 8.49 (s, 1H), 8.04 1.047 (dd, 1H), 7.45 (d, 2H), 7.22 (d, 1H), 5.24 (s, 2H), δ = 8.62 (dd, 1H), 8.01 (dd, 1H), 7.86 1.048 (dd, 1H), 7.45 (d, 2H), 6.95 (d, 1H), 5.20 (s, 2H) Biological Examples 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 cultivation (post-emergence) under controlled conditions in a glasshouse (at 24/16^oC, day/night; 14 hours light; 65% humidity), the plants are sprayed with an aqueous spray solution derived from the dissolution of the test compound in acetone and IF50 (11.12% Emulsogen EL360 TM + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether) which was then diluted to the required concentration using 0.2% Genapol XO80 (CAS No.9043-30-5) in water as the diluent. Test compounds are applied at the rates stated. The test plants are then grown in a glasshouse under controlled conditions in a glasshouse (at 24/16^oC, day/night; 14 hours light; 65% humidity) and watered twice daily. After 13 days for pre- and post-emergence, the test is evaluated for the percentage damage caused to the plant. TABLE B1. Post-emergence Test Compound Rate (g/ha) AMAPA AMARE SETFA ECHCG IPOHE 1_{.001 250} ^{5 5 NT 5 4} 1_{.002 250} ^{5 5 NT 5 4} 1_{.003 250} ^{5 4 NT 4 2} 1_{.004 250} ^{5 5 NT 4 3} 1_{.005 250} ^{5 5 5 4 3} 1_{.006 250} ^{5 5 5 5 4} 1_{.007 250} ^{5 5 4 4 3} 1_{.008 250} ^{NT 5 5 5 3} 1_{.009 250} ^{4 4 4 3 3} 1_{.010 250} ^{3 3 1 1 2} 1_{.011 250} ^{3 2 1 1 2} 1_{.012 250} ^{4 5 5 5 4} 1_{.013 250} ^{3 4 2 2 2} 1_{.014 250} ^{3 3 1 1 2} 1_{.015 250} ^{1 1 1 1 1} 1_{.016 250} ^{1 1 1 1 1} 1_{.017 250} ^{1 1 1 1 1} 1_{.018 250} ^{3 3 1 1 3} 1_{.019 250} ^{5 5 5 4 4} 1_{.020 250} ^{5 5 3 3 2} 1_{.021 250} ^{1 1 1 2 1} 1_{.022 250} ^{4 5 4 4 NT} 1_{.023 250} ^{5 5 5 5 NT} 1_{.024 250} ^{4 5 4 4 NT} Compound Rate (g/ha) AMAPA AMARE SETFA ECHCG IPOHE 1_{.025 250} ^{4 5 1 1 NT} 1_{.026 250} ^{4 4 1 1 NT} 1_{.027 250} ^{3 4 2 2 3} 1_{.028 250} ^{2 1 1 1 2} 1_{.029 250} ^{3 4 1 1 2} 1_{.030 250} ^{3 4 1 1 3} 1_{.031 250} ^{1 1 1 1 1} 1_{.032 250} ^{5 5 4 4 3} 1_{.033 250} ^{4 5 4 4 3} 1.034 250 2 2 1 1 3 1_{.035 250} ^{1 1 1 1 1} 1_{.036 250} ^{4 4 2 1 3} 1_{.037 250} ^{1 1 1 1 1} 1_{.038 250} ^{5 5 4 4 3} 1_{.039 250} ^{5 5 4 4 3} 1_{.040 250} ^{5 5 5 5 4} 1_{.041 250} ^{5 5 4 4 4} 1_{042 250} ^{5 5 1 1 1} 1_{.043 250} ^{5 5 4 4 3} 1_{.044 250} ^{5 5 5 5 5} 1_{.045 250} ^{5 5 5 5 5} 1_{.046 250} ^{5 5 5 5 NT} NT = Not tested

TABLE B2. Pre-emergence Test Compound Rate (g/ha) AMAPA AMARE SETFA ECHCG IPOHE 1_{.001 250} ^{5 5 NT 5 5} 1_{.002 250} ^{5 5 NT 5 5} 1_{.003 250} ^{5 5 NT 4 4} 1_{.004 250} ^{5 5 NT 5 5} 1_{.005 250} ^{5 5 5 5 5} 1_{.006 250} ^{5 5 5 5 5} 1_{.007 250} ^{5 5 5 5 4} 1_{.008 250} ^{5 5 5 5 5} 1.009 250 5 5 5 5 5 1_{.010 250} ^{3 4 1 1 1} 1_{.011 250} ^{1 1 1 1 1} 1_{.012 250} ^{5 5 5 5 5} 1_{.013 250} ^{4 3 3 2 4} 1_{.014 250} ^{1 1 1 1 1} 1_{.015 250} ^{1 1 1 1 1} 1_{.016 250} ^{1 1 1 1 1} 1_{.017 250} ^{2 2 3 2 1} 1_{.018 250} ^{4 2 1 1 1} 1_{.019 250} ^{5 5 5 5 5} 1_{.020 250} ^{5 5 4 2 1} 1_{.021 250} ^{1 1 1 1 1} 1_{.022 250} ^{5 5 4 4 NT} 1_{.023 250} ^{5 5 5 5 NT} 1_{.024 250} ^{5 5 4 5 NT} 1_{.025 250} ^{4 5 2 2 NT} 1_{.026 250} ^{5 5 1 1 NT} 1_{.027 250} ^{4 4 1 1 1} 1_{.028 250} ^{1 1 1 1 1} 1_{.029 250} ^{5 5 1 1 4} 1_{.030 250} ^{5 4 2 1 2} 1_{.031 250} ^{1 1 1 1 1} 1_{.032 250} ^{5 5 5 5 5} 1_{.033 250} ^{5 5 5 5 5} 1_{.034 250} ^{5 5 1 1 5} 1_{.035 250} ^{1 1 1 1 1} 1_{.036 250} ^{5 5 NT 1 4} 1_{.037 250} ^{1 1 1 1 1} 1_{.038 250} ^{5 5 5 5 2} 1_{.039 250} ^{5 5 5 5 5} 1_{.040 250} ^{5 5 5 5 5} 1_{.041 250} ^{5 5 5 5 5} 1042 250 4 5 4 3 1 1_{.043 250} ^{5 5 5 5 5} 1_{.044 250} ^{5 5 5 5 5} 1_{.045 250} ^{5 5 5 5 5} 1_{.046 250} ^{5 5 5 5 NT} NT = Not tested

Claims

Claims 1. A compound of Formula (I): Q

or an agronomically acceptable salt thereof, wherein Q is phenyl or a C-linked 6-membered heteroaryl wherein said phenyl or 6- membered heteroaryl is optionally substituted by one or more R⁴; R¹ is independently selected from the group consisting of halogen, -CN, NO₂, C₁-C₄alkyl, C₁-C₄haloalkyl, C₃-C₆cycloalkyl, C₂-C₄alkenyl, C₂-C₄alkynyl, - S(O)pC1-C4alkyl, C1-C4alkoxy-, -C(O)C1-C4alkyl, -C(O)OC1-C4alkyl, C1- C4haloalkoxy and C1-C4alkoxyC1-C3alkyl-; R² is selected from the group consisting of halogen, -CN, NO2, C1-C4alkyl, C1- C4haloalkyl, C1-C4alkoxy, -C(O)C1-C4alkyl, -C(O)OC1-C4alkyl, C1- C4haloalkoxy, C1-C4alkoxyC1-C3alkyl-, C1-C4alkoxyC1-C3alkoxy-, C1- C4alkoxyC1-C3alkoxyC1-C3alkyl-, -C(R⁷)=NOR⁸, -S(O)pC1-C4alkyl and C3- C6cycloalkyl; R³ is selected from the group consisting of hydrogen, halogen, C1-C4 alkyl, C1-C4alkoxyC1-C3alkyl-, C1- C3alkoxyC1-C3alkyl-, -CN, NO2, C2- -S(O)pC1-C4haloalkyl, -C(O)OC1

- C4alkyl and -C(O)NR⁵R⁶; R⁴ is selected from the group consisting of halogen, C1-C4 alkyl, C1- C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4alkoxyC1-C3alkyl-, C1- C₄alkoxyC₁-C₃alkoxy-, C₁-C₄alkoxyC₁-C₃alkoxyC₁-C₃alkyl-, -CN, NO₂, C₂- -S(O)_pC₁-C₄haloalkyl, -C(O)OC₁-

R⁵ is hydrogen or C₁-C₄alkyl; R⁶ is hydrogen or C₁-C₄alkyl; R⁷ is hydrogen or C₁-C₄alkyl; R⁸ is hydrogen or C₁-C₂alkyl; m = is 0, 1 or 2; and p = 0, 1 or 2.

2. A compound according to claim 1, wherein R³ is hydrogen.

3. A compound of Formula (I) according to claim 1 or claim 2, wherein m is one or two and R¹ is independently selected from the group consisting of halogen, -CN, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy- and C1-C4haloalkoxy.

4. A compound according to claim 3, wherein m is one and R¹ is chloro.

5. A compound according to any one of the previous claims, wherein R² is -CF3 or -CF2H.

6. A compound according to any one of the previous claims, wherein Q is selected from the group consisting of:

wherein n is 0, 1 or 2.

7. A compound according to any one of the previous claims, wherein Q is Q-1 or Q-3.

8. A compound according to claim 7, wherein n is 1 or 2.

9. A compound according to claim 8, wherein R⁴ is independently selected from the group consisting of cyano, methyl, halogen and -CF₃.

10. A compound according to any one of the previous claims, wherein Q is 4-Cl- phenyl-.

11. A herbicidal composition comprising a compound according to any one of the previous claims and an agriculturally acceptable formulation adjuvant.

12. A herbicidal composition according to claim 11, further comprising at least one additional pesticide.

13. A herbicidal composition according to claim 12, wherein the additional pesticide is a herbicide or herbicide safener.

14. A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of a composition according to any one of claims 11 to 13.

15. Use of a compound of Formula (I) as defined in claim 1 as a herbicide.