Herbicidal imidazole compound

Abstract

The present invention relates to a compound of formula (I), JPEG2025524614000101.jpg6099(wherein A, Q, R 1 , R 2 , R 3 and m are as defined herein), or an agriculturally acceptable salt of said compound. The present invention further relates to a herbicidal composition comprising a compound of formula (I), and, in particular, to the use of a compound of formula (I) for controlling weeds in crops of useful plants.

Description

Technical Field

[0001] The present invention relates to herbicidal compounds, processes for their preparation, herbicidal compositions containing the compounds, and their use, in particular for weed control in useful plant crops or for inhibiting plant growth.

[0002] Certain imidazole compounds have been disclosed in the prior art, such as in Chinese Patent No. 106317072 and International Publication No. 2022 / 015975. However, no herbicidal uses that may contain such imidazole compounds have been reported yet.

Summary of the Invention

Means for Solving the Problems

[0003] Therefore, according to the present invention, formula (I):

Chemical Formula

[0004] C1-C4 alkyl and C1-C6 alkyl include, 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-C2 alkyl is methyl (Me, CH3) or ethyl (Et, C2H5).

[0005] 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.

[0006] C1-C8 haloalkyl- 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, heptafluoro-n-propyl and perfluoro-n-hexyl. C1-C4 haloalkyl- and C1-C2 haloalkyl include, 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.

[0007] C1-C4 alkoxy and C1-C3 alkoxy include, for example, methoxy and ethoxy.

[0008] C1-C8 haloalkoxy- and C1-C8 haloalkoxy- include, 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.

[0009] C2-C8 alkenyl- includes, for example, -CH=CH2 (vinyl) and -CH2-CH=CH2 (allyl).

[0010] C2-C8 alkynyl- is composed of only carbon and hydrogen atoms, contains at least one triple bond, and refers to a straight-chain or branched hydrocarbon chain radical group having 2 to 4 carbon atoms, which is bonded to the rest of the molecule by a single bond. Examples of C2-C4 alkynyl include, but are not limited to, prop-1-ynyl, propargyl (prop-2-ynyl), and but-1-ynyl.

[0011] C1-C4 alkyl-S-(alkylthio) includes, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio.

[0012] C1-C4 alkyl-S(O)-(alkylsulfinyl) includes, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.

[0013] C1-C4 alkyl-S(O)2-(alkylsulfonyl) includes, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

[0014] In one embodiment of the present invention, A is N. In another embodiment of the present invention, m is 1. Therefore, in a preferred embodiment of the present invention, the formula (Ia)

Chemical formula

[0015] In one embodiment of the present invention, A is CR 11 , and R 11 is selected from the group consisting of hydrogen, fluoro, chloro and CN, preferably fluoro or hydrogen. Therefore, in a preferred embodiment of the present invention, the formula (Ib)

Chemical formula

[0016] In one embodiment of the present invention, a compound of formula (I), formula (Ia) or formula (Ib) is provided, where R 1 is chloro.

[0017] In one embodiment of the present invention, a compound of formula (I), formula (Ia) or formula (Ib) is provided, where R 2 is halogen (e.g., Cl or Br) or C1-C4 haloalkyl (e.g., -CF3, -CHF2).

[0018] In one embodiment of the present invention, a compound of formula (I), formula (Ia) or formula (Ib) is provided, where R 3 is hydrogen or halogen (e.g., Cl).

[0019] In a preferred embodiment of the present invention, a compound of formula (I), formula (Ia) or formula (Ib) is provided, where Q is C2-C8 alkyl or C2-C6 alkyl (e.g., -CH2CH(CH3)2, n-butyl, n-pentyl), C2-C8 alkenyl (e.g., -CH2CH2CH=CH2), C1-C8 haloalkyl or C1-C6 haloalkyl (e.g., -CH2CH2CHF2, -CH2CH2CF3, -CH2CH2CH2CF3), C1-C4 alkoxy-C1-C3 alkyl- (e.g., -CH2OCH3, -CH2CH2OCH3), C1-C4 haloalkoxy-C1-C3 alkyl- (e.g., -CH2OCH2CHF2, -CH2CH2OCH2CHF2), -S(O) p R 4 (e.g., -SO2CH2CH2CF3, -S-CH2CH2CF3) and -(CH2) n R 10selected from the group consisting of, for example, -CH2CH2CH2OH, -CH2CH2C(H)(OH)CH2OH, -CH2CH2C(H)O)-OH, -CH2CH2C(H)=N-OH, -CH2CH2C(H)=N-O-CH3 and -CH2CH2C(H)=N-O-CH2-cPr

[0020] In one embodiment of the present invention, a compound of formula (I), formula (Ia) or formula (Ib) is provided, wherein Q is -(CH2) n R 10 and n is 1, 2 or 3, and 10 R is -OH (for example, -CH2CH2CH2OH), -C(H)(OH)-CH2OH (for example, -CH2CH2C(H)(OH)CH2OH), -C(H)=NOR 5 (for example, -CH2CH2C(H)=N-OH, -CH2CH2C(H)=N-O-CH3, -CH2CH2C(H)=N-O-CH2-cPr) and -NR 12 R 13 selected from the group consisting of, for example, -CH2CH2CH2N(CH3)SO2CH3.

[0021] In a preferred embodiment of the present invention, a compound of formula (I), formula (Ia) or formula (Ib) is provided, wherein Q is C2-C8 alkyl (for example, -CH2CH(CH3)2, n-butyl, n-pentyl).

[0022] In another preferred embodiment of the present invention, a compound of formula (I), formula (Ia) or formula (Ib) is provided, wherein Q is C1-C8 haloalkyl (for example, -CH2CH2CHF2, -CH2CH2CF3, -CH2CH2CH2CF3).

[0023] In another preferred embodiment of the present invention, a compound of formula (I) or formula (Ia) is provided, wherein Q is C1-C4 haloalkoxy-C1-C3 alkyl- (for example, -CH2OCH2CHF2, -CH2CH2OCH2CHF2).

[0024] The present invention further provides a compound of formula Int-1: [Chemical formula] relates to the compound of formula (I), where R 2 and R 3 are as defined with respect to formula (I) above. In a preferred embodiment, R 2 is C1-C4 haloalkyl (e.g., -CHF2 or -CF3), and R 3 is hydrogen. In a more preferred embodiment, the compound of formula (Int-1) is compound I18 [Chemical formula] as follows.

[0025] The present invention further relates to a compound of formula (IIIa-1): [Chemical formula] wherein R 1a is halogen (e.g., F or Cl), and R 14 is C1-C4 alkyl (e.g., ethyl). In a more preferred embodiment, the compound of formula (IIIa-1) is compound I28 [Chemical formula] as follows.

[0026] The compounds of formula (I) may contain chiral centers, may exist as a single enantiomer, as a pair of enantiomers in any ratio, or, when two or more chiral centers are present, may contain all possible ratios of diastereoisomers. Typically, one of the enantiomers has a higher biological activity compared to the other possibilities.

[0027] The present invention also provides an agriculturally acceptable salt of the compound of formula (I). The salts of the compounds of formula (I) may be formed with amines such as primary, secondary, and tertiary amines (e.g., ammonia, dimethylamine, and triethylamine), and alkali metal and alkaline earth metal bases, transition metals, or quaternary ammonium bases are preferred.

[0028] Although the compounds of formula (I) of the present invention can be used as herbicides per se, they are generally formulated into herbicide compositions using formulation aids such as carriers, solvents, and surfactants (SAA). Therefore, the present invention further provides a herbicide composition comprising a herbicide compound according to any one of the preceding claims and an agriculturally acceptable formulation aid. The composition may be in the form of a concentrate to be diluted before use, but it is also possible to produce a composition that can be used as is. The final dilution is usually carried out with water, but it can also be carried out with, for example, liquid fertilizers, trace elements, biological organisms, oils, or solvents instead of water or in addition to water.

[0029] The herbicide composition usually contains 0.1 to 99% by weight, particularly 0.1 to 95% by weight, of the compound of formula I and 1 to 99.9% by weight of the formulation aid, and the formulation aid preferably contains 0 to 25% by weight of the surface active substance.

[0030] The composition can be selected from several types of formulations. These include emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), oil-in-water emulsions (EO), water-in-oil (EW) emulsions, microemulsions (ME), oily suspensions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), industrial concentrates (TK), dispersible concentrates (DC), soluble powders (SP), wettable powders (WP), and soluble granules (SG). The type of formulation selected in any case will depend on the specific intended purpose and the physical, chemical, and biological properties of the compound of formula (I).

[0031] 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 polysaccharides), and optionally one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve the water dispersibility / solubility. The mixture is then ground into a fine powder. Similar compositions can also be granulated into water-soluble granules (SG).

[0032] 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, preferably one or more dispersing agents, and optionally one or more suspending agents to promote dispersion in a liquid. The mixture is then ground into a fine powder. Similar compositions can also be granulated into water-dispersible granules (WG).

[0033] Granules (GR) can be formed by granulating a mixture of a compound of formula (I) and one or more powdered solid diluents or carriers, or by absorbing a compound of formula (I) (or a solution thereof in a suitable medicament) into a porous granular material (such as pumice, attapulgite clay, fuller's earth, kieselguhr, diatomaceous earth or ground corn cob) from pre-formed blank granules, or by adsorbing a compound of formula (I) (or a solution thereof in a suitable medicament) onto a hard core material (such as sand, silicate, carbonate, sulfate or phosphate mineral) and drying if necessary. Agents commonly used to assist absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketones and esters) and fixing agents (such as polyvinyl acetate, polyvinyl alcohol, dextrin, saccharides and vegetable oils). One or more other additives may also be included in the granules (for example, emulsifiers, wetting agents or dispersing agents).

[0034] The dispersible concentrate (DC) can be prepared by dissolving the compound of formula (I) in water or an organic solvent such as a ketone, an alcohol or a glycol ether. These solutions may contain a surfactant (for example, to improve dilution with water or to prevent crystallization in the spray tank).

[0035] The emulsifiable concentrate (EC) or the oil-in-water emulsion (EW) can be prepared by dissolving the compound of formula (I) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifiers or a mixture of said agents). Suitable organic solvents for use in EC 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), dimethylamides of fatty acids (such as dimethylamides of C8-C 10 dimethylamides of fatty acids etc.) and chlorinated hydrocarbons. The EC product can, upon addition of water, spontaneously emulsify to give an emulsion having sufficient stability for spray application by a suitable device.

[0036] The preparation of EW involves obtaining the compound of formula (I) as a liquid (which can typically be melted at a moderate temperature below 70 °C if it is not liquid at room temperature) or as a solution (by dissolving in a suitable solvent), and then emulsifying the resulting liquid or solution in water containing one or more SAAs under high shear to obtain an emulsion. Suitable solvents for use in EW include vegetable oils, chlorinated hydrocarbons (such as chlorobenzene), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes), and other suitable organic solvents having low solubility in water.

[0037] Microemulsions (ME) can be prepared by mixing a blend of one or more solvents and one or more SAAs with water to naturally yield a thermodynamically stable isotropic liquid formulation. The compound of formula (I) is initially present in water or the solvent / SAA blend. Suitable solvents for use in ME include those described above herein for use in EC or EW. ME can be a water-in-oil or oil-in-water system (which system is present can be determined by conductivity measurements) and can be suitable for the mixing of water-soluble and oil-soluble pesticidal agents into the same formulation. ME is suitable as a microemulsion as such or for dilution with water to form a conventional water-in-oil emulsion.

[0038] Suspension concentrates (SC) can comprise an aqueous or non-aqueous suspension of fine insoluble solid particles of the compound of formula (I). SC can be prepared by subjecting the solid compound of formula (I) in a suitable medium, optionally together with one or more dispersants, to a ball mill or bead mill 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, the compound of formula (I) can be subjected to a dry mill and added to water containing the agents described above hereinbefore to yield the desired final product.

[0039] Aerosol formulations comprise the compound of formula (I) and a suitable propellant (e.g., n-butane). The compound of formula (I) can also be dissolved or dispersed in a suitable medium (e.g., water, or a hydratable liquid such as n-propanol) to yield a composition for use with a non-pressurized manual spray pump.

[0040] The capsule suspension (CS) can be prepared in the same manner as the preparation of the EW formulation, but an aqueous dispersion of oil droplets is obtained, and each of the oil droplets is encapsulated by a polymeric shell and can be prepared with an additional polymerization stage so as to contain the compound of formula (I) and optionally a carrier or diluent therefor. The polymeric shell can be produced by an interfacial polycondensation reaction or a coacervation method. This composition can provide controlled release of the compound of formula (I), and they can be used for seed treatment. The compound of formula (I) can also be incorporated into a biodegradable polymer matrix to provide a controlled sustained release of the compound.

[0041] The composition may contain one or more additives to improve the biological performance of the composition, for example, by improving the wettability, retention, or dispersibility of the compound of formula (I) on the surface; the resistance to rain on the treated surface; or the uptake or mobility. Such additives include surfactants (SAA), oil-based spray additives such as certain mineral oils or natural vegetable oils (such as soybean and rapeseed oils), modified vegetable oils such as methylated rapeseed oil (MRSO), and blends of these with other bio-enhancing adjuvants (formulation components that can assist or modify the action of the compound of formula (I)).

[0042] The wetting agent, dispersing agent, and emulsifying agent may be cationic, anionic, amphoteric, or nonionic SAA.

[0043] Suitable cationic SAA include quaternary ammonium compounds (such as cetyltrimethylammonium bromide), imidazolines, and amine salts.

[0044] Suitable anionic SAAs include alkali metal salts of fatty acids, salts of aliphatic monoesters of sulfuric acid (e.g., sodium lauryl sulfate), salts of sulfonated aromatic compounds (e.g., sodium dodecylbenzenesulfonate, calcium dodecylbenzenesulfonate, butylnaphthalene sulfonic acid, and a mixture of sodium di-isopropyl-sulfonate and sodium tri-isopropyl-naphthalenesulfonate), ether sulfates, alcohol ether sulfates (e.g., sodium laureth-3-sulfate), ether carboxylates (e.g., sodium laureth-3-carboxylate), phosphate esters (reaction of one or more aliphatic alcohols with phosphoric acid (mainly mono-esters) or phosphorus pentoxide (mainly di-esters), e.g., the product of the reaction of lauryl alcohol with metaphosphoric acid; further, these products may be ethoxylated), sulfosuccinates, paraffin or olefin sulfonates, taurates, lignosulfonates, and phosphates / sulfates of tristyrylphenol.

[0045] Suitable amphoteric SAAs include betaines, propionates, and glycineates.

[0046] Suitable nonionic 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 alkylphenols (such as octylphenol, nonylphenol, or octylcresol); partial esters derived from long-chain fatty acids or hexitol anhydrides; condensation products of the partial esters with ethylene oxide; block polymers (including ethylene oxide and propylene oxide); alkanolamides; simple esters (such as fatty acid polyethylene glycol esters); amine oxides (such as lauryldimethylamine oxide); lecithin and sorbitan and their esters, alkyl polyglycosides, and tristyrylphenol.

[0047] Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone, or sodium carboxymethylcellulose), and swelling clays (such as bentonite or attapulgite).

[0048] The compounds of the present invention can also be used in mixtures with one or more further herbicides and / or plant growth regulators. Examples of such further herbicides or plant growth regulators include acetochlor, acifluorfen (including acifluorfen-sodium), acronifen, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, bentriazone, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, bilanafos, bipyrazon, bispyribac-sodium, bixlozone, bromacil, bromoxynil, butachlor, butaphenacil, carfentrazone (including carfentrazone-ethyl), chloransulam (including chloransulam-methyl), chlormuron (including chlormuron-ethyl), chlorotoluron, chlorosulfuron, cinmethylin, clazifos, clethodim, clodinafop (including clodinafop-propargyl), chlormazone, clopyralid, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cyhalofop (including cyhalofop-butyl), 2,4-D (including its choline salt and 2-ethylhexyl ester), 2,4-DB, desmedipham, dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), diclosulam, diflufenican, diflufenzoppil, dimethachlor, dimethenamid-P, dioxopyrimetryn, diquat dibromide, diuron, epirifluorfen, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenpyrazone, fenquinotrione, fentrazamide, flazasulfuron, florasulam, flupyradifurone (including flupyradifurone-benzyl), fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), flufenacet, flumetsulam, flumioxazin, flumetsuron, fomesafen, flupyrsulfuron (including flupyrsulfuron-methyl-sodium), fluroxypyr (including fluroxypyr-meptyl), fomesafen, foramsulfuron,Glufosinate (including L - glufosinate and both ammonium salts), glyphosate (including its diammonium, isopropylammonium, and potassium salts), halauxifen (including halauxifen - methyl), haloxyfop (including haloxyfop - methyl), hexazinone, hidantocidin, imazamox (including R - imazamox), imazapic, imazapyr, imazethapyr, indaziflam, iodosulfuron (including iodosulfuron - methyl - sodium), iofensulfuron (including iofensulfuron - sodium), ioxynil, isoproturon, isoxaflutole, rankotriol, MCPA, MCPB, mecoprop - P, mesosulfuron (including mesosulfuron - methyl), mesotrione, metazachlor, metazachlor, metazachlor, methiozolin, metolachlor, metosulam, metribuzin, methosulfuron, napropamide,nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, phenmedipham, picloram, pinoxaden, pretilachlor, primisulfuron - methyl, prometryn, propanil, propaquizafop, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen (including pyraflufen - ethyl), pyrazosulfuron - ethyl, pyridate, pyriftalid, pyrimisulfan, pyroxasulfone, pyroxysulam, cinchlorac, cinmethylin, quizalofop (including quizalofop - P - ethyl and quizalofop - P - tefuryl), rimsulfuron, rimsulfuron, flufenacet, sethoxydim, simazine, S - metolachlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn, tetfurylpyrimeth, thienacarbazone, thifensulfuron, thiafenacet, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, tribenuron (including tribenuron - methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron - sodium), trifludimoxazin, trifluralin, triflusulfuron, tripyrasulfone,Ethyl 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-carboxylate, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one, 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-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-methylimidazolidin-2-one, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (including its agriculturally acceptable esters, such as 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-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)-[,2,4]triazolo[4,3-a]pyridine-8-carboxamide3-(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, tetrahydrofuran-2-ylmethyl (2R)-2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoate, tetrahydrofuran-2-ylmethyl 2-[(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)methyl 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxyphenyl)-pyrimidine-4-carboxylate, and 6-amino-5-chloro-2-(4-chloro-2-fluoro-3-methoxy-phenyl)-pyrimidine-4-carboxylic acid are included.

[0049] The mixing partner of the compound of formula (I) may also be in the form of an ester or a salt, for example, as described in The Pesticide Manual, Sixteenth Edition, British Crop Protection Council, 2012.

[0050] The compound of formula (I) can also be used in a mixture with other pesticides such as fungicides, nematicides or insecticides, examples of which are shown in The Pesticide Manual.

[0051] The mixing ratio of the compound of formula (I) to the mixing partner is preferably 1:100 to 1000:1.

[0052] This mixture can be advantageously used in the above formulations (in which case the "active ingredient" relates to each mixture of the compound of formula (I) and the mixing partner).

[0053] The compound or mixture of the present invention can also be used in combination with one or more herbicide phytotoxicity reducing agents. Examples of such phytotoxicity reducing agents include benoxacor, cloquintocet (including cloquintocet - mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole - ethyl), fenclorim, flurioxypyr, furilazole, isoxadifen (including isoxadifen - ethyl), mefenpyr (including mefenpyr - diethyl), metcamifene and oxabetrinil.

[0054] Particularly preferred is a mixture of the compound of formula (I) with cyprosulfamide, isoxadifen - ethyl, cloquintocet - mexyl and / or metcamifene.

[0055] The phytotoxicity reducing agent of the compound of formula (I) can also be, for example, as described in The Pesticide Manual, 16 thAs described in the Edition (BCPC), 2012, it may be in the form of an ester or a salt. References to crocintoxet-mexyl also apply to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as disclosed in International Publication No. 02 / 34048.

[0056] Preferably, the mixing ratio of the compound of formula (I) to the phytotoxicity reducing agent is 100:1 to 1:10, particularly 20:1 to 1:1.

[0057] The present invention further provides a method for controlling weeds at a location, which includes applying to the location a composition containing an amount of the compound of formula (I) that controls weeds. Further, the present invention can further provide a method for selectively controlling weeds at a location containing crop plants and weeds, which includes applying to the location a composition of the present invention in an amount that controls weeds. "Control" means killing, reducing or delaying growth, or preventing or reducing germination. It is noted that the compounds of the present invention exhibit much improved selectivity compared to known structurally similar compounds. Generally, the plants to be controlled are unwanted plants (weeds). "Location" means an area where plants are growing or will grow. The application may be applied to the location before and / or after the emergence of crop plants. Multiple crop plants may be essentially resistant to the herbicidal effect of the compound of formula (I). Preferred crop plants include corn, wheat, barley and rice.

[0058] The application rate of the compound of formula I may vary within a wide range and also depends on the nature of the soil, the application method (before emergence or after emergence; seed dressing; application to furrows; application to non-cultivated land, etc.), crop plants, weeds to be controlled, prevailing climatic conditions, and other factors depending on the application method, application time, and target crop. The compound of formula I of the present invention is usually applied in an amount of 10 to 2500 g / ha, particularly 25 to 1000 g / ha, and further 25 to 250 g / ha.

[0059] Application is generally effected by spraying the composition with a large - area sprayer typically mounted on a tractor, but other methods such as dusting (in the case of powders), dripping or irrigation are also possible.

[0060] Crop plants also include crop plants that have been given resistance to other herbicides or herbicide classes (e.g., ALS -, GS -, EPSPS -, PPO -, HPPD -, PDS -, and ACCase - inhibitors) by conventional breeding methods or genetic engineering. Examples of crop plants given resistance to imidazolinones such as imazamox by conventional breeding methods are Clearfield® summer rape (canola). Examples of crop plants given herbicide resistance by recombinant methods include, for example, glyphosate - and glufosinate - resistant maize varieties marketed under the trade names RoundupReady® and LibertyLink®. The compounds of the present invention may be used in combination with, for example, the plants disclosed in International Publication No. WO 2020 / 236790.

[0061] Crop plants should also be understood as those to which resistance to harmful insects has been conferred by genetic engineering methods, such as, for example, Bt maize (resistant to the European corn borer), Bt cotton (resistant to the pink bollworm), and Bt potato (resistant to the Colorado potato beetle). An example of Bt maize is the Bt176 maize hybrid from NK® (Syngenta Seeds). The Bt toxin is a natural protein formed by the soil bacterium Bacillus thuringiensis. Examples of toxins, or of genetically modified plants capable of synthesizing such toxins, are described in EP 451 878, EP 374 753, WO 93 / 07278, WO 95 / 34656, WO 03 / 052073, and EP 427 529. Examples of genetically modified plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potato), NatureGard® and Protexcta®. Both the plant crop and its seed material can be resistant to herbicides and, at the same time, resistant to feeding by insects ("stacked" genetically modified organisms). For example, the seeds can be glyphosate-resistant and, at the same time, capable of expressing an insecticidal Cry3 protein.

[0062] Crop plants should also be understood as including those obtained by conventional breeding methods or genetic engineering and containing so-called output traits (such as improved storage stability, higher nutritional value, and improved flavor).

[0063] The composition can be used to control unwanted plants (collectively referred to as "weeds"). The weeds to be controlled can be, for example, monocotyledonous plant species such as Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria, and Sorghum, and also dicotyledonous plant species such as Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola, and Xanthium.

[0064] In a further aspect of the invention, there is provided the use of a compound of formula (I) as defined herein as a herbicide.

[0065] Process for the preparation of a compound of formula (I) A process for the preparation of a compound, such as a compound of formula (I) which may optionally be its agrochemically acceptable salt, is described herein and forms a further aspect of the invention.

[0066] The compound of formula I-3 has Q, R 2 , A and R 1 (m) as defined in formula I, and wherein, R 31is a compound of formula I where C1-C4 alkyl, and, for example, a compound of formula I-1 Scheme 1: [Chemical formula] (wherein Q, R 2 , A and R 1 (m) are as defined in formula I, and also, X 1 is chlorine, bromine or iodine), and a compound of formula II (wherein R 31 is C1-C4 alkyl, and Yb1 can be, for example, B(OH)2 or B(ORb1)2 (where Rb1 can be a C1-C4 alkyl group, or two ORb1 groups can together with the boron atom form a 5-membered ring, such as a pinacol boronate ester) and other boron-derived functional groups) can be prepared by a Suzuki reaction including a reaction (Scheme 1) with. This reaction is carried out in the presence of a base such as sodium carbonate, tripotassium phosphate or cesium fluoride, for example, in a solvent or solvent mixture such as dioxane, acetonitrile, N,N-dimethyl-formamide, a mixture of 1,2-dimethoxyethane and water or a dioxane / water mixture, or a toluene / water mixture, preferably under an inert atmosphere, with a palladium-based catalyst such as 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). The reaction temperature can preferably range from room temperature to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation. Such Suzuki reactions are well known to those skilled in the art.

[0067] The compound of formula I-4 is R in formula I 3is a compound of formula I wherein the radical is CN and can be prepared from a compound of formula I-1 by reaction (cyanation) with M-CN IIa, where M is a metal coordinated to the cyanide. Examples of cyanating reagents include NaCN, Zn(CN)2, or potassium ferrocyanide. This reaction is carried out in the presence of a base such as sodium carbonate, tripotassium phosphate or cesium fluoride, in a solvent or solvent mixture such as dioxane, acetonitrile, N,N-dimethyl-formamide, a mixture of 1,2-dimethoxyethane and water or a dioxane / water mixture, or a toluene / water mixture, preferably under an inert atmosphere, and can be catalyzed by a palladium-based catalyst such as tetrakis(triphenylphosphine)palladium(0), (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium-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). The reaction temperature can preferably range from room temperature to the boiling point of the reaction mixture, or the reaction can be carried out under microwave irradiation. Such reactions are well known to those skilled in the art.

[0068] The compound of formula I-*1* can be prepared, for example, by a halogenation reaction of a compound of formula I-*2* (wherein Q, R2, A and R 1 (m) are as defined in formula I) with a halogenating reagent such as N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS) or N-iodosuccinimide (NIS), optionally in the presence of an additive such as p-toluenesulfonic acid. Alternatively, the halogenation may involve chlorine, bromine or iodine. Such halogenation reactions are carried out in a suitable solvent such as chloroform, carbon tetrachloride, 1,2-dichloroethane, acetic acid, diethyl ether, acetonitrile or N,N-dimethylformamide at a temperature of 20 to 200 °C, preferably from room temperature to 100 °C.

[0069] The compound of formula I-2 is prepared by reacting the compound of formula IV with a reagent of formula III (wherein A and R 1 (m) are as defined in formula I, and where LG1 is halogen, preferably iodine, bromine or chlorine (or a pseudo-halogen leaving group such as (halo)alkyl or phenylsulfonic acid ester, such as triflate), sodium hydride, or in the presence of a base such as an alkaline earth metal hydride, carbonate (such as 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, N,N-dimethylacetamide or acetonitrile, at a temperature of 0 to 120 °C, by reacting by a method well known to those skilled in the art.)

[0070] Alternatively, the compound of formula I-2 can be prepared according to Scheme 1a. In Scheme 1a, the compound of formula I-2 is prepared from the compound of formula IVaa via a decarboxylation reaction. Scheme 1a:

Chemical formula

[0071] The compound of formula IV can be prepared by the condensation reaction of the compound of formula VI or its hydrate form with the compound of formula V in the presence of ammonia or its alternatives such as ammonium hydroxide. This reaction can be carried out in the presence of solvents such as methanol, tetrahydrofuran, ethanol, etc., and at a temperature of 20 - 200 °C, preferably room temperature - 100 °C. The compound of formula VI or its hydrate form (wherein R 2 is as defined in formula I) can be prepared by the hydrolysis of the compound of formula VII (wherein R 2 is as defined in formula I). Such a two-step reaction is well-known in the literature.

[0072] The compound of formula I-5 is the compound of formula I (wherein Q, A and R 1 (m) are as defined in formula I, and here, R 3 in formula I is H, and R 2 in formula I is halogen defined as X 2 ). (Scheme 2) Scheme 2:

Chemical formula

[0073] The compound of formula I-5 is obtained by reacting the compound of formula VIII with the reagent of formula III (wherein A and R 1 (m) are as defined in formula I, and here, LG1 is halogen, preferably iodine, bromine or chlorine (or a pseudo-halogen leaving group such as (halo)alkyl or phenylsulfonic acid ester, such as triflate), and in the presence of a base such as sodium hydride, or an alkaline earth metal hydride, carbonate (such as 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, N,N-dimethylacetamide or acetonitrile, etc., at a temperature of 0 - 120 °C, and by reacting in a manner well-known to those skilled in the art.

[0074] The compound of formula VIII is prepared by reacting the compound of formula IX with CX 2 4XII (wherein X 2 is halogen, preferably chlorine or bromine) in the presence of triphenylphosphine. This reaction can be carried out in the presence of a solvent such as acetonitrile, carbon tetrachloride or tetrahydrofuran, and at a temperature from room temperature to the boiling point of the solvent. Such reactions are known in the literature and are described, for example, in Org. Lett. 2004, 6, 6, 929-931.

[0075] The compound of formula IX can be prepared by amide coupling of the compound of formula X and the compound of formula XI. The reaction can optionally be carried out by using an amide coupling reagent such as 1-propanephosphonic anhydride, (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazol[4,5-b]pyridinium 3-oxide hexafluorophosphate, etc. in the presence of a base such as pyridine, triethylamine, etc. Such reactions are well-known to those skilled in the art and are described in the literature.

[0076] The compound of formula I-6 is the compound of formula I (wherein Q, A and R 1 (m) are as defined in formula I, and here, R in formula I 2 is halogen and X 4 as defined) (Scheme 3). Scheme 3:

Chemical formula

[0077] The compound of formula I-6 is the compound of formula XVIII and the reagent of formula III (wherein A and R 1 (m)is as defined in formula I, and here, LG1 is a halogen, preferably iodine, bromine or chlorine (or a pseudo-halogen leaving group such as (halo)alkyl or phenylsulfonic acid ester, such as triflate), and sodium hydride, or an alkaline earth metal hydride, carbonate (such as sodium carbonate, potassium carbonate or cesium carbonate) or hydroxide and other bases, optionally in the presence of potassium iodide in an inert solvent such as tetrahydrofuran, dioxane, water, N,N-dimethylformamide DMF, N,N-dimethylacetamide or acetonitrile, etc., at a temperature of 0 to 120 °C, and can be prepared by reacting by a method well-known to those skilled in the art.

[0078] The compound of formula XVIII (wherein Q is as defined in formula I and X 4 is a halogen) can be prepared from the compound of formula XVII (wherein PG1 is an N-protecting group, such as an amino protecting group such as acetyl, trimethylsilylethoxymethyl (SEM), tert-butyloxycarbonyl, etc.) by a protecting group deprotection reaction. Such a reaction is well-known to those skilled in the art and can be carried out using, for example, a base catalyst or an acid catalyst such as HCl.

[0079] The compound of formula XVII can be prepared from the compound of formula XVI (wherein X 4 and X 5 are halogens) by a selective dehalogenation reaction. Such a reaction can be carried out by metal-halogen exchange using an organometallic reagent such as butyllithium, Grignard reagent or organozinc reagent, and further deactivation of the reaction with water or an acidic aqueous solution.

[0080] The compound of formula XVI can be prepared by a substitution reaction or a cross-coupling reaction of the compound of formula XIV with a compound of formula XV (wherein M is an alkali metal such as lithium or potassium, an alkaline earth metal such as magnesium, or a transition metal such as copper or zinc). The reaction can optionally be carried out in the presence of a metal catalyst such as palladium or copper, and in the presence of a ligand such as a phosphine ligand such as PPh3 or a nitrogen-containing ligand for copper such as 1,2-dimethylethylenediamine. The reaction can be carried out in the presence of a solvent such as tetrahydrofuran, dioxane or toluene. Alternatively, the compound of formula XVI can be prepared by a substitution reaction involving metal-halogen exchange of the compound of formula XIV with an organometallic reagent such as butyllithium or a Grignard reagent, and a further reaction with a compound of formula XVa (wherein LG2 is a halogen, preferably iodine, bromine or chlorine (or a pseudo-halogen leaving group such as (halo)alkyl or phenylsulfonic acid ester, such as triflate)) in an inert solvent such as tetrahydrofuran, dioxane, N,N-dimethylformamide DMF, N,N-dimethylacetamide, etc. at a temperature of -80 °C to 120 °C by a method well known to those skilled in the art.

[0081] The compound of formula XIV can be prepared from the compound of formula XIII by introduction of a protecting group. Such a reaction can be carried out in the presence of a base such as sodium hydride, potassium carbonate, sodium carbonate, etc., and in the presence of a suitable protecting group reagent such as 2-(chloromethoxy)ethyl-trimethyl-silane, acetyl chloride, di-tert-butyl dicarbonate, etc., and in the presence of a solvent such as tetrahydrofuran, methanol, water, acetonitrile, dimethylformamide, etc. Such reactions are well known in the literature.

[0082] The compound of formula I-7 is a compound of formula I (wherein Q, A and R 1 (m) are as defined in formula I, and wherein X 6 and X 7 are halogens) (Scheme 4). Scheme 4:

Chem.

[0083] The compound of formula I-7 can be prepared from the compound of formula XXIII (wherein X 6 and X 7 are halogen) according to a method similar to that described in Scheme 3 for the conversion of the compound of formula XVIII to the compound of formula I-6. The compound of formula XXIII can be prepared from the compound of formula XXII according to a method similar to that described in Scheme 3 for the conversion of the compound of formula XVII to the compound of formula XVIII. The compound of formula XXII can be prepared by deprotonation of the compound of formula XX with a suitable base such as a strong base like butyllithium or lithium diisopropylamide, followed by a substitution reaction with the compound of formula XXI (wherein LG3 is a halogen, preferably iodine, bromine or chlorine (or a pseudo-halogen leaving group such as (halo)alkyl or phenylsulfonic acid ester, such as triflate)). This reaction can generally be carried out in the presence of a solvent such as tetrahydrofuran or toluene and at a temperature in the range of -80 °C to room temperature. The compound of formula XX can be prepared from the compound of formula XIX according to a method similar to that described in Scheme 3 for the conversion of the compound of formula XIII to the compound of formula XIV.

[0084] Alternatively, the compound of formula I-1 can be prepared according to Scheme 5. In Scheme 5, the compound of formula I-1 can be prepared from the compound of formula XXVII via a fluorination reaction using a fluorination reagent such as diethylaminosulfur trifluoride or bis(2-methoxyethyl)aminosulfur trifluoride. Scheme 5:-

Chem.

[0085] The compound of formula I (wherein R 3 is H, and R 2 is -C(H)=NOR 7and R 7 7 (as defined in formula I above) can be represented by a compound of formula I-9. The compound of formula I-9 can be prepared by the condensation reaction of a compound of formula XXVII with a compound of formula XXVIIa. Such reactions are well known in the literature.

[0086] The compound of formula XXVII is prepared by reacting a compound of formula XXV with a compound of formula XXVI (wherein LG3 is a halogen, preferably iodine, bromine or chlorine (or a pseudo-halogen leaving group such as (halo)alkyl or phenylsulfonic acid ester, such as triflate, etc.)) in the presence of a base such as sodium hydride, or an alkaline earth metal hydride, carbonate (such as 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, at a temperature of 0 to 120 °C, by a method well known to those skilled in the art. The compound of formula XXV can be prepared from the compound of formula XXIV through an oxidation reaction using an oxidizing agent such as an alcohol oxidation reagent such as MnO2, SO3, pyridine, pyridinium dichromate or pyridinium chlorochromate. The compound of formula XXIV can be prepared according to the methods reported in the literature such as J.Med.Chem.1995,38,2251-2255. Scheme 6: [Chemical Structure]

[0087] Alternatively, the compound of formula XXV can be prepared from the compound of formula XXVIII (wherein PG3 is an N-protecting group such as N,N-dimethylsulfamoyl, acetyl, tert-butyloxycarbonyl, etc.) via an N-deprotection reaction. Such a deprotection reaction can be carried out in the presence of an acid catalyst such as hydrochloric acid or a base such as sodium hydroxide or potassium carbonate. The compound of formula XXVIII can be prepared from the compound of formula XXIX via a metallation reaction using a strong base such as n-butyllithium or lithium diisopropylamide, and then reacting with N,N-dimethylformamide to introduce an aldehyde. The compound of formula XXIX can be prepared from the compound of formula XXX via an N-protection reaction. Examples of reagents that can be used in such an N-protection reaction are di-tert-butyl dicarbonate, acetyl chloride, acetic anhydride, N,N-dimethylsulfamoyl chloride, etc.

[0088] Scheme 7:

Chemical Structure

[0089] The following non-limiting examples provide specific synthetic methods for representative compounds of the present invention as set forth in the following table.

[0090] Example 1: Preparation of 5-chloro-2-[[4-chloro-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methyl]pyrimidine (Compound 1.001)

Chemical formula

Chemical formula

[0091] Step 2: Preparation of 4-chloro-2-(4,4,4-trifluorobutyl)-1H-imidazole (I2) [Chemical formula] Carbon tetrachloride (0.39 mL, 4.00 mmol) was added to a stirred suspension of N-(cyanomethyl)-5,5,5-trifluoropentanamide I1 (210 mg, 1.08 mmol) and triphenylphosphine (1.07 g, 4.00 mmol) in acetonitrile (5 mL) under a nitrogen atmosphere. The reaction mixture was heated at 50 °C for 1 hour and then cooled to room temperature. The reaction mixture was diluted with aqueous 2M sodium hydroxide (50 mL) and then extracted with ethyl acetate (3 × 50 mL). The organics were combined, washed with brine (100 mL), dried over magnesium sulfate, and concentrated to give the crude product. The crude material was subjected to column chromatography on silica gel using 0 - 100% ethyl acetate in cyclohexane to give 4-chloro-2-(4,4,4-trifluorobutyl)-1H-imidazole I2 (88 mg, purity 70%). 1 H NMR (400 MHz; CDCl3) δ = 6.69 (s, 1H), 2.63 (t, 2H), 2.08 - 1.92 (m, 2H), 1.92 - 1.80 (m, 2H)

[0092] Step 3: Preparation of 5-chloro-2-[[4-chloro-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methyl]pyrimidine (1.001) [Chemical formula] 4-Chloro-2-(4,4,4-trifluorobutyl)-1H-imidazole I2 (88 mg), 5-chloro-2-(chloromethyl)pyrimidine hydrochloride (103 mg, 0.52 mmol), potassium carbonate (144 mg, 1.03 mmol), potassium iodide (6.9 mg, 0.041 mmol), acetonitrile (4 ml) and water (0.13 ml) were heated at 80 °C overnight. The reaction mixture was cooled to room temperature, then diluted with water (50 mL) and extracted with ethyl acetate (3 × 50 mL). The organics were combined, washed with brine (100 mL), dried over magnesium sulfate and concentrated to give the crude product. The crude material was subjected to column chromatography on silica gel using 0 - 50% ethyl acetate in cyclohexane to give 5-chloro-2-[[4-chloro-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methyl]pyrimidine 1.001 (50 mg, 14% in 2 steps). 1 H NMR (400 MHz; CDCl3) δ = 8.59 (s, 2H), 6.77 (s, 1H), 5.10 (s, 2H), 2.69 (t, 2H), 2.19 - 2.03 (m, 2H), 2.00 - 1.89 (m, 2H)

[0093] Example 2: Preparation of 5-chloro-2-[[4-(trifluoromethyl)-2-(3,3,3-trifluoropropyl)imidazol-1-yl]methyl]pyrimidine (Compound 1.002)

Chemical formula

Chemical formula

[0094] Step 2: Preparation of 4-(trifluoromethyl)-2-(3,3,3-trifluoropropyl)-1H-imidazole (I4)

Chemical formula

[0095] Step 3: Preparation of 5-chloro-2-[[4-(trifluoromethyl)-2-(3,3,3-trifluoropropyl)imidazol-1-yl]methyl]pyrimidine (1.002)

Chemical formula

[0096] Example 3: Preparation of 2-[[4-bromo-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methyl]-5-chloro-pyrimidine (Compound 1.003):

Chemical formula

Chemical formula

[0097] Preparation of step 2-2-[[4,5-dibromo-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methoxy]ethyl-trimethyl-silane (I6):

Chemical formula

[0098] Step 3 - Preparation of 2-[[4-bromo-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methoxy]ethyl-trimethyl-silane (I7):

Chemical formula

[0099] [[ID=X]] Step 4 - Preparation of 4-bromo-2-(4,4,4-trifluorobutyl)-1H-imidazole; hydrochloride (I8):

Chemical formula

[0100] Preparation of 5-chloro-2-[[4-bromo-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methyl]pyrimidine (Compound 1.003):

Chemical Structure

[0101] Example 4: Preparation of 5-chloro-2-[[4,5-dichloro-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methyl]pyrimidine (Compound 1.004):

Chemical Structure

Chemical formula

[0102] Preparation of 2-[[4,5-dichloro-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methoxy]ethyl-trimethyl-silane (I10):

Chemical formula

[0103] Step 3 - Preparation of 4,5-dichloro-2-(4,4,4-trifluorobutyl)-1H-imidazole (I11):

Chemical Structure

[0104] Step 4 - Preparation of 5-chloro-2-[[4,5-dichloro-2-(4,4,4-trifluorobutyl)imidazol-1-yl]methyl]pyrimidine 1.004:

Chemical Structure

[0105] Example 5: Preparation of 2-[[2-butyl-4-(difluoromethyl)imidazol-1-yl]methyl]-5-chloro-3-fluoro-pyridine (1.054)

Chemical Structure

Chemical Structure

[0106] Step 2: Preparation of 2-butyl-1H-imidazole-4-carbonitrile (I13)

Chem.

[0107] Step 3: Preparation of 2-butyl-1H-imidazole-4-carbaldehyde (I14)

Chem.

[0108] Step 4: Preparation of 2-butyl-1-[(5-chloro-3-fluoro-2-pyridyl)methyl]imidazole-4-carbaldehyde (I15) [Chemical Structure Diagram] 2-Butyl-1H-imidazole-4-carbaldehyde I14 (0.25 g, 1.64 mmol) was dissolved in acetonitrile (2.5 mL) in a 25 mL flask equipped with a nitrogen balloon. To this, potassium carbonate (0.56 g, 4.10 mmol) and potassium iodide (0.054 g, 0.32 mmol) were added, followed by 5-chloro-2-(chloromethyl)-3-fluoro-pyridine (0.35 g, 1.97 mmol). The reaction mixture was heated at 70 °C for 4 hours. After this time, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (3 × 50 mL). The combined organic layers were washed with brine (30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to obtain a crude product. This was purified by silica gel column chromatography using 0 - 40% ethyl acetate / cyclohexane to give 2-butyl-1-[(5-chloro-3-fluoro-2-pyridyl)methyl]imidazole-4-carbaldehyde I15 (0.16 g, 33%) as an off-white solid. 1 1H NMR (400 MHz, CDCl3) δ = 9.81 (s, 1H), 8.40 (d, 1H), 7.66 (s, 1H), 7.54 (dd, 1H), 5.25 (d, 2H), 2.74 - 2.81 (m, 2H), 1.71 - 1.81 (m, 2H), 1.36 - 1.50 (m, 2H), 0.90 - 0.99 (m, 3H).

[0109] Step 5: Preparation of 2-[[2-butyl-4-(difluoromethyl)imidazol-1-yl]methyl]-5-chloro-3-fluoro-pyridine (1.054)

Chem.

[0110] Example 6: Preparation of [1-[(5-chloropyrimidin-2-yl)methyl]-4-(trifluoromethyl)imidazol-2-yl]methanol (1.072)

Chem.

Chem.

[0111] Step 2: Preparation of tert-butyl-[[1-[(5-chloropyrimidin-2-yl)methyl]-4-(trifluoromethyl)imidazol-2-yl]methoxy]-dimethyl-silane (I17)

Chemical formula

[0112] Step 3: Preparation of [1-[(5-chloropyrimidin-2-yl)methyl]-4-(trifluoromethyl)imidazol-2-yl]methanol (1.072)

Chemical formula

[0113] Example 7: Preparation of 5-chloro-2-[[2-(difluoromethyl)-4-(trifluoromethyl)imidazol-1-yl]methyl]pyrimidine (1.070)

Chemical formula

Chemical formula

[0114] Step 2: Preparation of 5-chloro-2-[[2-(difluoromethyl)-4-(trifluoromethyl)imidazol-1-yl]methyl]pyrimidine (1.070)

Chemical formula

[0115] Example 8: Preparation of 5-chloro-2-[[2-(chloromethyl)-4-(trifluoromethyl)imidazol-1-yl]methyl]pyrimidine (1.071)

Chemical formula

[0116] Example 9: Preparation of 1-[(5-chloropyrimidin-2-yl)methyl]-2-(tetrahydrofuran-3-ylmethyl)imidazole-4-carbonitrile (1.073)

Chemical formula

Chemical formula

[0117] Step 2: Preparation of 2-(tetrahydrofuran-3-ylmethyl)-4-(trifluoromethyl)-1H-imidazole (I20)

Chemical formula

[0118] Step 3: Preparation of 2-(tetrahydrofuran-3-ylmethyl)-1H-imidazole-4-carbonitrile (I21)

Chemical formula

[0119] Step 4: Preparation of 1-[(5-chloropyrimidin-2-yl)methyl]-2-(tetrahydrofuran-3-ylmethyl)imidazole-4-carbonitrile (1.073)

Chemical formula

[0120] Example 10: Preparation of 1-[2-butyl-1-[(5-chloropyrimidin-2-yl)methyl]imidazol-4-yl]-N-methoxy-methanimine (1.076)

Chemical formula

Chemical formula

[0121] Step 2: Preparation of 2-butyl-4-formyl-N,N-dimethyl-imidazole-1-sulfonamide (I23)

Chemical formula

[0122] Step 3: Preparation of 2-butyl-1H-imidazole-4-carbaldehyde (I24)

Chemical formula

[0123] Step 4: Preparation of 2-butyl-1-[(5-chloropyrimidin-2-yl)methyl]imidazole-4-carbaldehyde (I25)

Chemical formula

[0124] Step 5: Preparation of 1-[2-Butyl-1-[(5-chloropyrimidin-2-yl)methyl]imidazol-4-yl]-N-methoxy-methanimine (1.076)

Chemical Structure

[0125] Example 11: Preparation of 2 - [[2 - butyl - 4 - (trifluoromethyl)imidazol - 1 - yl]methyl] - 5 - fluoropyrimidine (1.077)

Chemical Structure

Chemical Structure

[0126] Step 2: Preparation of ethyl 2-(5-fluoropyrimidin-2-yl)acetate (I27) [Chemical formula] A solution of diethyl 2-(5-fluoropyrimidin-2-yl)propanedioate I26 (500 mg, 1.95 mmol) in dimethyl sulfoxide (5 mL), sodium chloride (0.1403 g, 2.40 mmol) and water (0.125 mL) was heated at 150 °C for 7 hours. After this time, the reaction mass was quenched by the addition of water (100 mL) and extracted with ethyl acetate (3 × 200 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give the crude product. The crude reaction mass was purified by column chromatography using 30% ethyl acetate in cyclohexane to give ethyl 2-(5-fluoropyrimidin-2-yl)acetate I27 (250 mg, 69%) as a yellow gummy mass. 1 H NMR (400 MHz, CDCl3) δ = 8.58 (s, 2H), 4.25 (q, 2H), 4.04 (s, 2H), 1.27 (t, 3H).

[0127] Step 3: Preparation of ethyl 2-bromo-2-(5-fluoropyrimidin-2-yl)acetate (I28) [Chemical formula] A stirred solution of ethyl 2-(5-fluoropyrimidin-2-yl)acetate I27 (0.6 g, 3.25 mmol) in carbon tetrachloride (12 mL) was treated with benzoyl peroxide (0.08 g, 0.32 mmol), followed by N-bromosuccinimide (0.66 g, 3.64 mmol), and the mixture was heated to reflux for 6 h. After this time, the reaction mixture was cooled to room temperature and quenched by the addition of water (100 mL). The mixture was extracted with ethyl acetate (3 × 100 mL), dried over sodium sulfate, filtered, and concentrated to give the crude product. The crude reaction mass was purified by silica gel column chromatography using 30% ethyl acetate in cyclohexane to afford ethyl 2-bromo-2-(5-fluoropyrimidin-2-yl)acetate I28 (300 mg, 35%) as a yellow oil. 1 H NMR (400 MHz, CDCl3) δ = 8.63 (s, 2H), 5.69 (s, 1H), 4.30 (q, 2H), 1.31 (t, 3H).

[0128] Step 4: Preparation of ethyl 2-[2-butyl-4-(trifluoromethyl)imidazol-1-yl]-2-(5-fluoropyrimidin-2-yl)acetate (I29)

Chemical formula

[0129] Step 5: Preparation of 2 - [[2 - butyl - 4 - (trifluoromethyl)imidazol - 1 - yl]methyl] - 5 - fluoro - pyrimidine (1.077)

Chemical Structure

[0130] Example 12: Preparation of 2 - [[2 - butyl - 4 - (difluoromethyl)imidazol - 1 - yl]methyl] - 5 - chloro - pyrimidine (1.053)

Chemical Structure

[0131] Example 13: Preparation of 3-[1-[(5-chloropyrimidin-2-yl)methyl]-4-(trifluoromethyl)imidazol-2-yl]-N-methoxy-propan-1-imine (1.051)

Chemical formula

Chemical formula

[0132] Step 2: Preparation of 2-[[2-but-3-enyl-4-(trifluoromethyl)imidazol-1-yl]methyl]-5-chloropyrimidine (I31)

Chemical Structure

[0133] Step 3: Preparation of 4-[1-[(5-chloropyrimidin-2-yl)methyl]-4-(trifluoromethyl)imidazol-2-yl]butane-1,2-diol (I32)

Chemical formula

[0134] Step 4: Preparation of 3-[1-[(5-chloropyrimidin-2-yl)methyl]-4-(trifluoromethyl)imidazol-2-yl]propanal (I33)

Chemical formula

[0135] Step 5: Preparation of 3-[1-[(5-chloropyrimidin-2-yl)methyl]-4-(trifluoromethyl)imidazol-2-yl]propan-1-ol (I34)

Chemical formula

[0136] Step 6: Preparation of 5-chloro-2-[[2-(3-chloropropyl)-4-(trifluoromethyl)imidazol-1-yl]methyl]pyrimidine (1.051)

Chemical Structure

[0137] Example 14: Preparation of 3-[1-[(5-chloropyrimidin-2-yl)methyl]-4-(trifluoromethyl)-imidazol-2-yl]-N-methoxy-propan-1-imine (1.007)

Chemical Structure

[0138] Example 15: Preparation of 5-chloro-2-[[2-(3,3-difluoropropyl)-4-(trifluoromethyl)-imidazol-1-yl]methyl]-pyrimidine (1.010)

Chem.

[0139]

Table 1-1

[0140]

Table 1-2

[0141]

Table 1-3

[0142]

Table 1-4

[0143]

Table 1-5

[0144]

Table 1-6

[0145]

Table 1-7

[0146]

Table 1-8

[0147]

Table 1-9

[0148]

Table 1-10

[0149]

Table 1-11

[0150]

Table 1-12

[0151]

Table 1-13

[0152]

Table 1-14

[0153]

Table 1-15

[0154]

Table 1-16

[0155] Biological Examples Seeds of various test species: Palmer amaranth (Amaranthus palmeri) (AMAPA), redroot pigweed (Amaranthus retroflexus) (AMARE), barnyard grass (Echinochloa crus-galli) (ECHCG), ivyleaf morning glory (Ipomoea hederacea) (IPOHE), giant foxtail (Setaria faberi) (SETFA) are sown in standard soil in pots. Under controlled conditions in a greenhouse (24 / 16 °C, day / night; 14 hours of light; 65% humidity), after 1 day of cultivation (before germination) or after 8 days of cultivation (after germination), an aqueous spray solution obtained from a formulation of the active ingredient in a acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN 9005-64-5) is sprayed onto the plants. Unless otherwise specified, the compound is applied at 250 g / ha. Thereafter, the test plants are cultivated in the greenhouse under controlled conditions in a greenhouse (24 / 16 °C, day / night; 14 hours of light; 65% humidity) and watered twice a day. 13 days after before and after germination, the test is evaluated for the percentage of damage caused to the plants. The biological activity is shown in the following table on a 5-point scale (5 = 81 - 100%; 4 = 61 - 80%; 3 = 41 - 60%; 2 = 21 - 40%; 1 = 0 - 20%).

[0156]

Table 2-1

[0157]

Table 2-2

[0158]

Table 3-1

[0159]

Table 3-2

Claims

1. Formula (I): 【Chemical 1】 wherein A is CR 11 or N; Q is C 2 to C 8 alkyl, C 2 to C 8 alkenyl, C 2 to C 8 alkynyl, C 1 to C 8 haloalkyl, C 2 to C 8 haloalkenyl, C 2 to C 8 haloalkynyl, C 1 to C 4 alkoxy-C 1 to C 3 alkyl-, C 1 to C 4 haloalkoxy-C 1 to C 3 alkyl-, C 1 to C 4 alkoxy-C 1 to C 3 haloalkyl-, C 1 to C 8 cyanoalkyl-, C 3 to C 6 cycloalkyl (optionally substituted with CN, fluoro or chloro), -S(O) p R 4 and -(CH 2 ) n R 10 selected from the group consisting of; R 1 is independently selected from the group consisting of halogen, -CN, C 1 ~C 2 alkyl, C 1 ~C 2 haloalkyl, C 3 ~C 6 cycloalkyl, C 1 ~C 2 alkoxy- and C 1 ~C 2 haloalkoxy-; R 2 is selected from the group consisting of halogen, -CN, NO 2 , C 1 ~C 4 alkyl, C 1 ~C 4 haloalkyl, C 1 ~C 4 alkoxy, -C(O)C 1 ~C 4 alkyl, -C(O)OC 1 ~C 4 alkyl, C 1 ~C 4 haloalkoxy, -S(O) p C 1 ~C 4 alkyl, -C(R 6 )=NOR 7 and C 3 ~C 6 cycloalkyl; R 3 is selected from the group consisting of hydrogen, halogen, C 1 to C 4 alkyl, C 1 to C 4 haloalkyl, C 1 to C 4 alkoxy, C 1 to C 4 haloalkoxy, -CN, NO 2 , C 2 to C 4 alkenyl, C 2 to C 4 alkynyl, -S(O) p C 1 to C 4 alkyl, -S(O) p C 1 to C 4 haloalkyl, -C(O)OC 1 to C 4 alkyl and -C(O)NR 8 R 9 ; and R 4 is selected from the group consisting of C 1 to C 4 alkyl, C 1 to C 4 haloalkyl and C 3 to C 6 cycloalkyl; R 5 is selected from the group consisting of hydrogen, methyl, ethyl, -(CH 2 ),-cyclopropyl, C 2 to C 3 alkenyl, C 2 to C 3 alkynyl and cyclopropyl; R 6 is selected from the group consisting of hydrogen, methyl and ethyl; R 7 is methyl or ethyl; R 8 is hydrogen or C 1 to C 4 alkyl; R 9 is hydrogen or C 1 ~C 4 alkyl; R 10 is -OH, -C(H)O, -C(O)R 4 , -S(O) p R 4 , -C(H)(OH)-CH 2 OH, -C(R 6 ))=NOR 5 , -NR 12 R 13 , C 3 ~C 6 cycloalkyl (optionally substituted with CN, fluoro or hydroxy), C containing one or more oxygen atoms 3 ~C 6 saturated heterocycle, and 5-membered heteroaryl containing 1 to 3 heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulfur, where the heteroaryl is halogen, cyano, C 1 ~C 2 alkyl, C 1 ~C 2 haloalkyl, C 3 ~C 4 cycloalkyl, C 1 ~C 2 alkoxy and C 1 ~C 4 haloalkoxy, and may be optionally substituted with one or two substituents independently selected from the group consisting of; R 11 is selected from the group consisting of hydrogen, fluoro, chloro and CN; R 12 and R 13 are independently selected from the group consisting of C 1 to C 4 alkyl, C 3 to C 4 cycloalkyl, C 1 to C 4 alkyl-S(O) p -, C 3 to C 4 cycloalkyl-S(O) p -, C 1 to C 4 alkyl-C(O)- and C 3 to C 4 cycloalkyl-C(O)-; m = 1 or 2; n = 1, 2 or 3; and p = 0, 1 or 2) compound, or an agriculturally acceptable salt thereof.

2. Formula (Ia) 【Chemical 2】 (wherein Q, R 1 , R 2 and R 3 are as defined in claim 1 above) The compound of formula (I) according to claim 1, which is such.

3. R 1 is chloro, the compound according to claim 1 or 2.

4. R 2 is halogen or C 1 ~C 4 The compound according to any one of claims 1 to 3, which is haloalkyl.

5. R 3 The compound according to any one of claims 1 to 4, wherein R is hydrogen or halogen.

6. Q is C 2 to C 8 alkyl, C 2 to C 8 alkenyl, C 1 to C 8 haloalkyl, C 1 to C 4 alkoxy-C 1 to C 3 alkyl-, C 1 to C 4 haloalkoxy-C 1 to C 3 alkyl-, -S(O) p R 4 and -(CH 2 ) n R 10 The compound according to any one of claims 1 to 5, selected from the group consisting of

7. Q is -(CH 2 ) n R 10 , n is 1, 2 or 3, and R 10 is selected from the group consisting of -OH, -C(H)(OH)-CH 2 OH and -C(H)=NOR 5 ; a compound according to claim 6

8. Q is C 2 ~C 8 The compound according to claim 6, wherein it is alkyl.

9. Q is C 1 ~C 8 The compound according to claim 6, wherein Q is a haloalkyl.

10. Q is C 1 -C 4 haloalkoxy-C 1 -C 3 alkyl-, the compound according to claim 6.

11. A herbicidal composition comprising the compound according to any one of claims 1 to 10 and an agriculturally acceptable formulation adjuvant.

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

13. The herbicidal composition according to claim 12, wherein the additional pesticide is a herbicide or a herbicide phytotoxicity reducer.

14. A method for controlling weeds at a location, comprising applying to the location a composition according to any one of claims 11 to 13 in an amount effective to control weeds.

15. Use of the compound of formula (I) according to claim 1 as a herbicide.

16. Formula Int-1: 【Chemical Formula 3】 (wherein R 2 and R 3 are as defined in claim 1) compound.

17. Formula (IIIa-1): 【Chemical Formula 4】 (wherein, R 1a is halogen, and R 14 is C 1 - C 4 alkyl) compound.

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