Substituted benzamides as herbicides.

Abstract

The present invention relates to a compound represented by formula (I) [Formula 1] TIFF2024540946000019.tif5062 (in the formula, R 1 , R 2 , R 3 , R 4 and R 5 are as described herein) or an agriculturally acceptable salt thereof. The present invention further relates to compositions comprising said compounds, methods of controlling weeds using said compositions and the use of compounds of formula (I) as herbicides.

Description

[Technical field]

[0001] The present invention relates to herbicidal compounds, processes for their preparation, herbicidal compositions containing the compounds and their use for controlling weeds or inhibiting the growth of plants in crops of particularly useful plants. [Background technology]

[0002] N-(tetrazol-5-yl)arylcarboxamides are disclosed, for example, in WO 2012 / 028579.The present invention relates to novel arylcarboxamides that exhibit unexpectedly good weed control. Summary of the Invention [Means for solving the problem]

[0003] Thus, according to the present invention, a compound of formula (I): [ka] (In the formula, R 1 is selected from the group consisting of C1-C4 alkyl-, C1-C4 haloalkyl-, C1-C4 alkoxy-C1-C4 alkyl- and C1-C4 haloalkoxy-C1-C4 alkyl-; R 2 is halogen, C1-C6 alkyl-, C1-C3 alkoxy-, C1-C6 haloalkyl-, C1-C3 haloalkoxy- and -S(O) p Selected from the group consisting of C1-C6 alkyl; R 3 is C1-C3 haloalkyl; R 4 is selected from the group consisting of hydrogen, C1-C6 alkyl-, C1-C6 haloalkyl, and C3-C6 cycloalkyl; R 5is selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C1-C6-alkoxy-C1-C6 alkyl-, C1-C6-alkoxy-, phenyl and heteroaryl, wherein phenyl or heteroaryl is selected from the group consisting of one, two or three R 6 may be optionally substituted by substituents; R 6 is independently selected from the group consisting of halogen, cyano, C1-C6 alkyl (e.g., methyl), C1-C6 haloalkyl-, and C1-C6 alkoxy-; and p is 0, 1 or 2. or an agriculturally acceptable salt thereof. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0004] Examples of C1-C6 alkyl groups include 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).

[0005] C3-C6 cycloalkyl- includes cyclopropyl (c-propyl (c-Pr)), cyclobutyl (c-butyl (c-Bu)), cyclopentyl (c-pentyl) and cyclohexyl (c-hexyl).

[0006] C1-C3 alkoxy- and C1-C6 alkoxy include, for example, methoxy- and ethoxy-.

[0007] C1-C6-alkoxy-C1-C6 alkyl- includes, for example, methoxyethyl-.

[0008] Halogen (or halo) includes fluorine, chlorine, bromine or iodine. The same applies correspondingly to halogen in relation to other definitions, such as haloalkyl.

[0009] Examples of C1 to C6 haloalkyl include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2,2-difluoroethyl, 1,1-difluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl, 2,2,2-trichloroethyl, heptafluoro-n-propyl, and perfluoro-n-hexyl. Examples of C1-C4 haloalkyl include 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-tetrafluoroethyl, 2,2,2-trichloroethyl, and heptafluoro-n-propyl.

[0010] C1-C4 alkoxy-C1-C4 alkyl- includes, for example, methoxyethyl-.

[0011] C1-C4 haloalkoxy-C1-C4 alkyl- includes, for example, trifluoromethoxyethyl-.

[0012] C1-C6 alkyl-S-(alkylthio) is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio.

[0013] C1-C6 alkyl-S(O)-(alkylsulfinyl) is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl, preferably methylsulfinyl or ethylsulfinyl.

[0014] C1-C6 alkyl-S(O)2-(alkylsulfonyl) is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl, preferably methylsulfonyl or ethylsulfonyl.

[0015] In a preferred embodiment of the present invention, R 1 is selected from the group consisting of methyl, ethyl and n-propyl, preferably methyl.

[0016] In a preferred embodiment of the present invention, R 2 is selected from the group consisting of methyl, Cl, -CF3 and -SO2 methyl, more preferably Cl.

[0017] In another preferred embodiment of the present invention, R 3 is -CF3 or -CHF2.

[0018] In another preferred embodiment of the present invention, R 4 is hydrogen or C1-C6 alkyl-(preferably methyl), most preferably methyl or hydrogen.

[0019] In another embodiment of the present invention, R 5 is C1 to C6 alkyl- (for example, methyl, ethyl or n-propyl, preferably methyl) or C3 to C6 cycloalkyl- (preferably cPr-).

[0020] In another preferred embodiment of the present invention, R 5 is -phenyl, wherein phenyl may be optionally substituted as previously described.

[0021] In another embodiment of the present invention, R 5is -heteroaryl, which may be optionally substituted as described above. In further preferred embodiments, heteroaryl is a 5- or 6-membered heteroaryl. In further preferred embodiments, heteroaryl is R 5a , R 5b , R 5c , R 5d , R 5e , R 5f , R 5g , R 5h , R 5i and R 5j : [ka] is selected from the group consisting of:

[0022] In a preferred embodiment of the present invention, heteroaryl is R which may be optionally substituted by one, two or three substituents selected from the group consisting of halogen, C1-C6 alkyl (e.g., methyl), C1-C6 haloalkyl and C1-C6 alkoxy. 5c In a further preferred embodiment of the invention, heteroaryl is R optionally substituted with one halogen, preferably fluorine. 5c It is.

[0023] In one embodiment of the present invention, R 4 is hydrogen or methyl, and R 5 is methyl, ethyl or n-propyl. In another embodiment of the present invention, R 4 is hydrogen or methyl, and R 5 is phenyl, which may be optionally substituted with one halogen, preferably fluorine. In another embodiment of the invention, R 4 is hydrogen or methyl, and R 5 is heteroaryl, which is optionally substituted by one halogen, preferably fluorine; 5c It is.

[0024] Compounds of formula (I) (and certain intermediate compounds used to synthesize compounds of formula (I)) may contain asymmetric centers and may exist as single enantiomers, as pairs of enantiomers in any ratio, or, when two or more asymmetric centers are present, may include diastereoisomers in all possible ratios. Typically, one of the enantiomers has greater biological activity than the other possible ones.

[0025] The present invention also includes all possible geometric and tautomeric forms of the compounds of formula (I).

[0026] The present invention also includes agriculturally acceptable salts which the compounds of formula (I) can form with amines (e.g. ammonia, dimethylamine and triethylamine), alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among the alkali metal and alkaline earth metal hydroxides, oxides, alkoxides and hydrogen carbonates and carbonates used as salt formers, the hydroxides, alkoxides, oxides and carbonates of lithium, sodium, potassium, magnesium and calcium are important, in particular the hydroxides, alkoxides, oxides and carbonates of sodium, magnesium and calcium. The corresponding trimethylsulfonium salts may also be used.

[0027] The compounds of formula (I) according to the present invention can be used as herbicides themselves, but they are generally formulated into herbicidal compositions using formulation auxiliaries such as carriers, solvents and surfactants (SFAs).The present invention therefore further provides a herbicidal composition comprising the herbicidal compounds according to the present invention and agriculturally acceptable formulation auxiliaries.The composition can be in the form of a concentrate that is diluted before use, but ready-to-use compositions can also be made.Final dilution is usually carried out with water, but can also be carried out with, for example, liquid fertilizers, micronutrients, biological organisms, oils or solvents instead of or in addition to water.

[0028] The herbicidal compositions generally comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of a compound of formula I and from 1 to 99.9% by weight of formulation auxiliaries, preferably including from 0 to 25% by weight of surface-active substances.

[0029] The compositions can be selected from a number of formulations, many of which are known from the Manual on Development and Use of FAO Specifications for Plant Protection Products, 5th Edition, 1999. These include dusts (DP), water-soluble powders (SP), water-soluble granules (SG), water-dispersible granules (WG), wettable powders (WP), granules (GR) (slow or immediate release), soluble concentrates (SL), oil-miscible liquids (OL), ultra-low liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsifiable concentrates (both oil-in-water (EW) and water-in-oil (EO)), microemulsions (ME), suspension concentrates (SC), aerosols, capsule suspensions (CS) and seed treatment formulations. In each case, the formulation selected will depend on the specific purpose envisaged and the physical, chemical and biological properties of the compound of formula (I).

[0030] Dusts (DP) may be prepared by mixing a compound of formula (I) with one or more solid diluents (e.g., natural clay, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earth, calcium phosphate, calcium and magnesium carbonate, sulfur, lime, flour, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.

[0031] Water-soluble (SP) can be prepared by mixing the 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 substances to improve dispersibility / solubility in water. This mixture is then ground into a fine powder. Similar compositions can also be granulated to form water-soluble granules (SG).

[0032] Wettable powders (WP) can be prepared by mixing the compound of formula (I) with one or more solid diluents or carriers, one or more wetting agents, and preferably one or more dispersing agents and optionally one or more suspending agents to facilitate dispersion in liquid. This mixture is then ground into a fine powder. Similar compositions can also be granulated to form wettable granules (WG).

[0033] Granules (GR) can be formed either by granulating a mixture of the compound of formula (I) with one or more powdered solid diluents or carriers, or by absorbing the compound of formula (I) (or its solution in a suitable material) into a porous granular material (such as pumice, attapulgite clay, fuller's earth, kieselguhr, diatomaceous earth or ground corn cob), or by granulating from preformed blank granules by adsorbing the compound of formula (I) (or its solution in a suitable material) onto a hard core material (such as sand, silicates, inorganic carbonates, sulfates or phosphates) and drying as required. Substances commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum-based solvents, alcohols, ethers, ketones and esters) and binders (such as polyvinyl acetate, polyvinyl alcohol, dextrin, sugars and vegetable oils). One or more other additives can also be included in the granules (e.g., emulsifiers, wetting agents or dispersants).

[0034] 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 surfactants (e.g. to improve water dilutability or prevent crystallization in the spray tank).

[0035] 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 emulsifiers or mixtures of said materials). Organic solvents suitable for use in ECs include aromatic hydrocarbons (such as alkylbenzenes or alkylnaphthalenes exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a registered trademark), ketones (such as cyclohexanone or methylcyclohexanone) and alcohols (such as benzyl alcohol, furfuryl alcohol or butanol), N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone), dimethylamides of fatty acids (C8-C9, C10-C12, C12-C16, C16-C18, C18-C2 ... 10 EC products include dimethylamides of fatty acids, and chlorinated hydrocarbons. EC products can emulsify spontaneously when added to water to produce emulsions that are stable enough to be spray-applied with appropriate equipment.

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

[0037] Microemulsions (MEs) can be prepared by mixing water with a blend of one or more SFAs and one or more solvents to spontaneously produce a thermodynamically stable isotropic liquid formulation. The compound of formula (I) is initially present in either the water or the solvent / SFA blend. Solvents suitable for use in MEs include those mentioned above for use in ECs or EWs. MEs can be either oil-in-water or water-in-oil systems (which system is present can be determined by conductivity measurements) and can be suitable for mixing water-soluble and oil-soluble pesticides in the same formulation. MEs are suitable for dilution in water and either remain microemulsions or form traditional oil-in-water emulsions.

[0038] 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 milling or bead milling a 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 settling rate of the particles. Alternatively, a compound of formula (I) may be dry milled and added to water containing the above-mentioned materials to produce the desired end product.

[0039] Aerosol formulations include a compound of formula (I) and a suitable propellant (e.g., n-butane). The compound of formula (I) may also be dissolved or dispersed in a suitable vehicle (e.g., water or a water-miscible liquid such as n-propanol) to obtain a composition for use in a non-pressurized, manually operated spray pump.

[0040] Capsule suspensions (CS) can be prepared in a similar manner to the preparation of EW formulations, except that each oil droplet is encapsulated by a polymeric shell, and an aqueous dispersion of oil droplets containing the compound of formula (I) and, optionally, a carrier or diluent therefor, is obtained with an additional polymerization step. The polymeric shell can be produced by either an interfacial polycondensation reaction or a coacervation procedure. This composition provides a controlled release of the compound of formula (I) and can be used for seed treatment. The compound of formula (I) can also be formulated in a biodegradable polymer matrix to provide a delayed controlled 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 wetting, retention or distribution on a surface; rain resistance on a treated surface; or uptake or mobility of the compound of formula (I). Such additives include surface active agents (SFAs), oil-based spray additives, such as certain mineral oils or natural vegetable oils (such as soybean oil and rapeseed oil), and blends of these with other bioenhancement aids (ingredients that can assist or modulate the action of the compound of formula (I)).

[0042] Wetting agents, dispersing agents and emulsifying agents can be SFAs of the cationic, anionic, amphoteric or non-ionic type.

[0043] Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethylammonium bromide), imidazolines and amine salts.

[0044] Suitable anionic SFAs 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 sulfonate and a mixture of di-isopropyl- and tri-isopropyl-naphthalenesulfonates), sulfate ethers, alcohol sulfate ethers (e.g., sodium laureth-3-sulfate), carboxylate ethers (e.g., sodium laureth-3-carboxylate), phosphate esters (products from the reaction of one or more aliphatic alcohols with phosphoric acid (mainly mono-esters) or phosphorus pentoxide (mainly di-esters), e.g., the reaction product of lauryl alcohol with tetraphosphoric acid; furthermore, these products may be ethoxylated), sulfosuccinamates, paraffin or olefin sulfonates, taurates and lignosulfonates.

[0045] Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.

[0046] Suitable SFAs 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 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 (including ethylene oxide and propylene oxide); alkanolamides; simple esters (e.g. fatty acid polyethylene glycol esters); amine oxides (e.g. lauryl dimethylamine oxide); and lecithin.

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

[0048] The compounds of the present invention may also be used in mixtures with one or more additional herbicides and / or plant growth regulators, such as acetochlor, acifluorfen (including acifluorfen-sodium), aclonifen, ametryn, aminocarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, benquitrione, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, vilanaphos, bipyrazone, bispyribac-sodium, bixlozone, bromacil, bromoxynil, butachlor, butafenacil, carfentra, etc. cyclosulfamuron, cyhalofop (including cyhalofop-butyl), 2,4-D (including choline salts and its 2-ethylhexyl ester), 2,4-DB, desmediol, 2,4-dimethylaminobutyric acid, 2,4-dimethylphenylsulfonate ... Fam, dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, dichloroprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), diclosulam, difluhenican, diflufenzopyr, dimethachlor, dimethenamid-P, dioxopyritrione, diquat dibromide, diuron, epirifenacil, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenpyra fenquinotrion, 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 both L-glufosinate and the ammonium salt), glyphosate (including its diammonium, isopropylammonium and potassium salts), haloxifen (including haloxyfop-methyl), haloxyfop (including haloxyfop-methyl), hexazinone, hydantocidin, imazamox (including R-imazamox), imazapic, imazapyr, imazethapyr, indaziflam, iodosulfuron (including iodosulfuron-methyl-sodium), iofensulfuron (including iofensulfuron-sodium). mesosulfuron (including mesosulfuron-methyl), ioxynil, isoproturon, isoxaflutole, lancotrione, MCPA, MCPB, mecoprop-P, mesosulfuron (including mesosulfuron-methyl), mesotrione, metamitron, metazachlor, methiozoline, metolachlor, metosulam, metribuzin, metsulfuron, napropamide, nicosulfuron, norflurazon, oxadiazon, oxasulfuron, oxyfluorfen, paraquat dichloride, pendimethalin, penoxsulam, phenmedipham, picloram, pinoxaden, pretiraclovir sulphuron, primisulfuron-methyl, prometryn, 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-metra Chlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn, tetflupyrolimeth, thiencarbazone, thifensulfuron, thiaphenacyl, torpiralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, tribenuron (including tribenuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), trifludimoxazine, 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]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-methyl-imidazolidin-2 -one, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid (including its agrochemically 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-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) 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-ylmethyl 2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]-propanoic acid 2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]propanoate, 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, 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.

[0049] The mixing partners of the compounds of formula I may also be in the form of esters or salts, as mentioned, for example, in The Pesticide Manual, Sixteenth Edition, British Crop Protection Council, 2012.

[0050] The compounds of formula I may also be used in mixtures with other pesticides, such as fungicides, nematicides or insecticides, examples of which are given 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] Mixtures may advantageously be used in the abovementioned formulations (in which case "active ingredient" relates to the respective mixture of compounds of formula I with the mixing partners).

[0053] 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 is the mixture of the compound of formula I with cyprosulfamide, isoxadifen-ethyl, cloquintocet mexyl and / or metcamifen.

[0054] The safeners of the compounds of formula I are described, for example, in The Pesticide Manual, 16 thEdition (BCPC), 2012. References to cloquintocet-mexyl also apply to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, references to fenchlorazole-ethyl also apply to fenchlorazole, etc., as disclosed in WO 02 / 34048.

[0055] Preferably, the mixing ratio of compound of formula I to safener is from 100:1 to 1:10, in particular from 20:1 to 1:1.

[0056] Mixtures may be advantageously used in the formulations described above (in which case "active ingredient" refers to the respective mixture of compound of formula I and safener).

[0057] The present invention further provides a method for controlling weeds in a habitat, comprising application to the habitat of the weeds of a composition comprising a controlling amount of a compound of formula (I). The present invention also provides a method for selectively controlling weeds in a habitat comprising crop plants and weeds, comprising application to the habitat of a weed controlling amount of a composition according to the present invention. By "control" is meant killing, reducing or retarding growth, or preventing or reducing germination. Generally, the plants to be controlled are unwanted plants (weeds). By "habitat" is meant the area in which the plants are growing or will grow. Some crop plants may be innately resistant to the herbicidal effect of the compounds of formula (I). However, in some cases, resistance may need to be artificially introduced into the crop plants, for example, by genetic engineering. Thus, it is possible to confer resistance to HPPD inhibitors to crop plants by genetic engineering. Methods for conferring resistance to HPPD inhibitors to crop plants are known, for example, from WO 0246387. Thus, in a more preferred embodiment, the crop plant is transgenic for a polynucleotide comprising a DNA sequence encoding an HPPD inhibitor-resistant HPPD enzyme from bacteria, more particularly from Pseudomonas fluorescens or Shewanella colwelliana, or an HPPD inhibitor-resistant HPPD enzyme from a plant, more particularly from a monocotyledonous plant or even more particularly from Barley, Maize, Wheat, Rice, Brachiaria, Cenchrus, Lolium, Festuca, Setaria, Eleusine, Sorghum or Avena species. A number of HPPD-resistant soybean transgenic "events" are known, including, for example, SYHT04R (WO 2012 / 082542), SYHT0H2 (WO 2012 / 082548), and FG72.Other polynucleotide sequences that can be used to produce plants that are tolerant to the compounds of the invention are disclosed, for example, in WO 2010 / 085705 and WO 2011 / 068567. Crop plants for which the compositions of the invention can be used thus include crops such as, for example, cereals such as barley and wheat, cotton, oilseed rape, sunflower, corn, rice, soybean, sugar beet, sugar cane and turf.

[0058] Crop plants may also include trees such as fruit trees, palm trees, coconut trees or other nuts. Also included are climbing plants such as grapes, fruit shrubs, fruit plants and vegetables.

[0059] The application rates of the 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 in the seed furrow; non-arable application, etc.), the crop, the weeds 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 rates of 10 to 2000 g / ha, in particular 50 to 1000 g / ha.

[0060] Application is generally by spraying the composition, typically with a tractor-mounted sprayer for large areas, although other methods such as dusting (for dusts), dripping or irrigation can also be used.

[0061] It should be understood that crops include those that have been made resistant to herbicides or classes of herbicides (e.g., ALS-, GS-, EPSPS-, PPO-, ACCase- and HPPD inhibitors) by conventional breeding methods or genetic engineering. An example of a crop that has been made resistant to imidazolinones, such as imazamox, by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been made resistant to herbicides by genetic engineering methods include, for example, glyphosate-resistant and glufosinate-resistant corn varieties available under the trade names RoundupReady® and LibertyLink®.

[0062] It should be understood that crops are also crops that have been rendered resistant to pests by genetic engineering methods, such as Bt corn (resistant to the corn borer), Bt cotton (resistant to the boll weevil) and even Bt potato (resistant to the Colorado potato beetle). An example of Bt corn is the Bt 176 corn hybrid from NK® (Syngenta Seeds). Bt toxins are proteins that are naturally formed by the Bacillus thuringiensis soil bacterium. Examples of toxins or transgenic plants capable of synthesizing such toxins are described in EP 451878, EP 374753, WO 93 / 07278, WO 95 / 34656, WO 03 / 052073 and EP 427529. Examples of transgenic plants that contain one or more genes that code for insecticide resistance and express one or more toxins are KnockOut® (corn), Yield Gard® (corn), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potato), NatureGard® and Protexcta®. Either the plant crop or its seed material can be resistant to herbicides and at the same time resistant to insect feeding ("multiple" transgenic events). For example, seeds can have the ability to express insecticidal Cry3 proteins and at the same time are resistant to glyphosate.

[0063] Crops should be understood to also include crops obtained by traditional breeding methods or by genetic modification and containing so-called output traits (eg improved storage stability, higher nutritional value and improved flavor).

[0064] Other useful plants include ornamental plants such as turfgrasses and flowers or shrubs grown commercially for turfgrass or lawns, for example, on golf courses, lawns, parks and roadsides.

[0065] The compositions may be used to control undesirable plants (collectively, "weeds"). The weeds controlled are monocotyledonous species such as Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eleusine, Lolium, Monochoria, Rottboellia, Sagittaria, Scirpus, Setaria, and the like. ), and Sorghum, as well as dicotyledonous species such as Abutilon, Amaranthus, Ambrosia, Chenopodium, Chrysanthemum, Conyza, Galium, Ipomoea, Nasturtium, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium. Weeds may also be considered crops, but may also include plants that grow outside of a crop area ("escapes") or plants that grow from seeds left over from a different previously planted crop ("volunteers"). Such volunteers or escapees may be resistant to certain other herbicides.

[0066] The compounds of the present invention can be prepared according to the following schemes.

[0067] Scheme 1 Compounds of formula (I) may be prepared from a benzoic acid of formula (II) and an amine of formula (III). [ka]

[0068] According to the above scheme, benzoic acid of formula (II) and amine of formula (III) are treated with a suitable amide coupling reagent in a suitable solvent. An additive that enhances the reaction rate may be optionally added. An example of a suitable amide coupling reagent is thionyl chloride. An example of a suitable solvent is pyridine. An example of a suitable additive is N-methylimidazole.

[0069] Scheme 2 Benzoic acids of formula (II) can be prepared from hydrolyzed esters of formula (IV), where "Alk" is defined as a C1-C6 alkyl group. [ka]

[0070] Treatment of the benzoic acid of formula (IV) with a hydroxide base, such as sodium hydroxide, in a suitable solvent, such as a 3:1 mixture of ethanol:water, gives the compound of formula (II).

[0071] Scheme 3 A compound of formula (IV) (wherein R 4 is not hydrogen) can be prepared from a compound of formula (V). [ka]

[0072] The compound of formula (V) is treated with a base, such as sodium hydride, and a compound of formula (VI), where LG is defined as a leaving group. One example of a suitable leaving group is iodide. For example, when R4 is methyl, the compound of formula (VI) is iodomethane.

[0073] Scheme 4 Compounds of formula (V) can be prepared from an aldehyde of formula (VII) and a primary amide of formula (VIII). [ka]

[0074] A compound of formula (VII) and a compound of formula (VIII) are treated with an acid, such as trifluoroacetic acid, and a reducing agent, such as triethylsilane, in a suitable solvent, such as toluene.

[0075] Scheme 6 Compounds of formula (VII) may be prepared from aldehydes of formula (IX). [ka]

[0076] Treatment of a compound of formula (IX) with an oxidizing agent such as Dess-Martin periodinane in a suitable solvent such as benzotrifluoride gives a compound of formula (VII).

[0077] Scheme 7 Compounds of formula (IX) can be obtained by carbonylation of aryl bromides of formula (X). [ka]

[0078] The compound of formula (X) is treated with carbon monoxide gas at a suitable pressure, for example 10 bar, in an autoclave with a suitable catalyst, for example [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) and a suitable base, for example triethylamine. The solvent is Alk-OH. For example, if the solvent is methanol, then "Alk" in the above scheme will be methyl.

[0079] Scheme 8 A compound of formula (X) may be prepared from a compound of formula (XI). [ka]

[0080] A compound of formula (XI) is treated with a reducing agent, such as sodium borohydride, in a suitable solvent, such as methanol.

[0081] Scheme 9 The compound of formula (XI) is R 3 and R 2 Depending on the nature of R 3 When R is trifluoromethyl and R2 is chloro, compounds of formula (X) may be prepared from commercially available 1-bromo-2-chloro-4-(trifluoromethoxy)benzene. [ka]

[0082] 1-Bromo-2-chloro-4-(trifluoromethoxy)benzene is treated with a base such as lithium diisopropylamide in a suitable solvent such as tetrahydrofuran, and N,N-dimethylformamide is then added to the reaction to give the compound of formula (XI).

[0083] Scheme 10 R 2 is chloro, and R 3 When is not trifluoromethyl, compounds of formula (X) may be prepared from commercially available 5-bromo-6-chloro-2-hydroxybenzaldehyde. [ka]

[0084] 5-Bromo-6-chloro-2-hydroxybenzaldehyde, R 3 The person skilled in the art is familiar with these reagents and knows which reagents are suitable for which R 3 For example, R3 When is difluoromethyl, an example of a suitable reagent is diethyl(bromodifluoromethyl)phosphonate.

[0085] The following non-limiting examples provide specific methods for the synthesis of representative compounds of the present invention referenced in Table 1 herein. EXAMPLES

[0086] Example 1: Preparation of compound 1.003. Step 1: Preparation of 3-bromo-2-chloro-6-(trifluoromethoxy)benzaldehyde To a stirred solution of 1-bromo-2-chloro-4-(trifluoromethoxy)benzene (15 g, 54 mmol) in THF (300 mL) was added lithium diisopropylamide (2.0 mol / L) in THF (32 mL) dropwise at -78 °C and the reaction was stirred at the same temperature for 1 h. To this solution was added anhydrous DMF (8.4 mL, 107.82 mmol) and the reaction was stirred at -78 °C for an additional 0.5 h. After completion, the mixture was quenched by dropwise addition of aqueous 1N HCl. The resulting aqueous solution was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to give the crude product, which was purified by flash chromatography on silica gel (cyclohexane:ethyl acetate gradient 99:1 to 90:10) to give 3-bromo-2-chloro-6-(trifluoromethoxy)benzaldehyde (13.0 g, 76%) as a yellow oil. 1H NMR(400MHz,DMSO-d6)δ ppm 10.28(s,1H)8.18(d,1H)7.52(d,1H)

[0087] Step 2: Preparation of [3-bromo-2-chloro-6-(trifluoromethoxy)phenyl]methanol To a stirred solution of 3-bromo-2-chloro-6-(trifluoromethoxy)benzaldehyde (13.0 g, 42.8 mmol) in methanol (95 mL) was added sodium borohydride (2.27 g, 60.0 mmol) in several portions at 0° C. The reaction mass was then stirred at ambient temperature for 2 hours. After completion, ice-cold water was added slowly to quench excess sodium borohydride, which was then concentrated to reduce methanol. The resulting solution was acidified with 2N HCl and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to give [3-bromo-2-chloro-6-(trifluoromethoxy)phenyl]methanol (13.0 g, 99% yield) as a pale yellow oil. 1H NMR(400MHz,DMSO-d6)δ ppm 7.88(d,J=9.03Hz,1H)7.36(d,J=8.78Hz,1H)5.38(t,J=5.40Hz,1H)4.65(d,J=5.52Hz,2H)

[0088] Step 3: Preparation of methyl 2-chloro-3-(hydroxymethyl)-4-(trifluoromethoxy)benzoate To a solution of [3-bromo-2-chloro-6-(trifluoromethoxy)phenyl]methanol (13.0 g, 42.6 mmol) in methanol (130 mL) was added 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (7 g, 8.51 mmol) and triethylamine (12 mL, 85.1 mmol). The reaction mixture was stirred at 95° C. under carbon monoxide atmosphere (10 atm) for 6 h. After reaction, the mixture was cooled to ambient temperature and diluted with water (100 mL). The resulting aqueous solution was extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude residue. The crude residue was purified by flash chromatography on silica gel (cyclohexane:ethyl acetate eluent gradient 99:1 to 80:20) to give methyl 2-chloro-3-(hydroxymethyl)-4-(trifluoromethoxy)benzoate (9.0 g, 68% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.83 (d, 1H) 7.50 (d, 1H) 5.36 (t, 1H) 4.65 (d, 2H) 3.89 (s, 3H).

[0089] Step 4: Preparation of methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate To a stirred solution of methyl 2-chloro-3-(hydroxymethyl)-4-(trifluoromethoxy)benzoate (5.0 g, 18 mmol) in trifluoromethylbenzene (50 mL) was added Dess-Martin periodinane (15 g, 35 mmol) in portions at 0-10 °C. The reaction was allowed to stir at ambient temperature for 3 h. After completion, the reaction mixture was cooled to 10 °C and diluted with saturated NaHCO3 solution. The resulting aqueous solution was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a crude residue. The crude residue was purified by flash chromatography on silica gel (cyclohexane:ethyl acetate eluent gradient 99:1 to 70:30) to give methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (3.0 g, 60% yield) as a yellow solid. 1H NMR(400MHz,DMSO-d6)δ ppm 10.35(s,1H)8.12(d,J=8.80Hz,1H)7.66(d,J=8.68,1H)3.91(s,3H)

[0090] Step 5: Preparation of methyl 2-chloro-3-[(propanoylamino)methyl]-4-(trifluoromethoxy)benzoate A microwave vial was charged with propanamide (776 mg, 10.62 mmol), 2,2,2-trifluoroacetic acid (0.82 mL, 11 mmol), methyl 2-chloro-3-formyl-4-(trifluoromethoxy)benzoate (1.00 g, 3.54 mmol, 100 ml), triethylsilane (1.7 mL, 11 mmol) and stirred in toluene (15 mL). The reaction mixture was heated in the MW at 160° C. for 2 h. The reaction mixture was then concentrated under reduced pressure and the residue was purified by flash column chromatography (0-50% gradient of ethyl acetate in cyclohexane). The product containing fractions were combined and concentrated in vacuum to give methyl 2-chloro-3-[(propanoylamino)methyl]-4-(trifluoromethoxy)benzoate as a white solid (540 mg, 1.590 mmol, 45%). 1H NMR (400MHz, chloroform) δ = 7.82-7.75 (m, 1H), 7.31-7.25 (m, 1H), 5.71-5.60 (m, 1H), 4.75-4.68 (m, 2H), 3.98-3.93 (m, 3H), 2.25-2.14 (m, 2H), 1.14 (t, J = 7.6Hz, 3H)

[0091] Step 6: Preparation of 2-chloro-3-[(propanoylamino)methyl]-4-(trifluoromethoxy)benzoic acid To a stirred solution of methyl 2-chloro-3-[(propanoylamino)methyl]-4-(trifluoromethoxy)benzoate (0.300 g, 0.883 mmol) in tetrahydrofuran (3.6 mL) and water (0.9 mL) at room temperature was added lithium hydroxide monohydrate (0.111 g, 2.65 mmol). The mixture was stirred at room temperature overnight. The reaction was quenched by the addition of 2 M aqueous HCl (10 mL). The mixture was stirred at room temperature for a further 5 min and then extracted three times with ethyl acetate. The combined organic phases were concentrated in vacuo to give 2-chloro-3-[(propanoylamino)methyl]-4-(trifluoromethoxy)benzoic acid (0.274 g, 0.841 mmol, 95%) as a beige solid. 1H NMR (400MHz, methanol) δ = 7.91-7.75 (m, 1H), 7.45-7.34 (m, 1H), 4.66-4.54 (m, 2H), 2.25-2.11 (m, 2H), 1.17-0.99 (m, 3H)

[0092] Step 7: Preparation of 2-chloro-N-(1-methyltetrazol-5-yl)-3-[(propanoylamino)methyl]-4-(trifluoromethoxy)benzamide 2-Chloro-3-[(propanoylamino)methyl]-4-(trifluoromethoxy)benzoic acid (275 mg, 0.844 mmol), 1-methyltetrazol-5-amine (100 mg, 1.009 mmol) were stirred in 3-methylpyridine (3 mL) under nitrogen atmosphere for 10 minutes. Triethylamine (0.18 mL, 1.3 mmol) was added to the reaction mixture followed by 1-methylimidazole (0.075 mL, 0.93 mmol) and stirred at room temperature for 30 minutes. The reaction mixture was then cooled to 0° C. and thionyl chloride (0.124 mL, 1.69 mmol) was added dropwise in such an amount that the temperature was maintained at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction mass was quenched with 2N HCl (10 ml) and stirred for 30 minutes. It was extracted twice with ethyl acetate and the combined organics were collected and concentrated in vacuum. The crude product was purified by reverse phase chromatography (30-60% gradient of acetonitrile in water). The product containing fractions were combined and the solvent was removed by lyophilization to give a preparation of 2-chloro-N-(1-methyltetrazol-5-yl)-3-[(propanoylamino)methyl]-4-(trifluoromethoxy)benzamide (150 mg, 0.3680 mmol, 44% yield) as a white solid. 1H NMR (400 MHz, methanol) δ ppm 1.13 (t, J = 7.64 Hz, 3H) 2.14-2.28 (m, 2H) 4.09 (s, 3H) 4.59-4.70 (m, 2H) 7.48-7.56 (m, 1H) 7.73-7.80 (m, 1H) 8.29 (br s, 1H).

[0093] [Table 1-1] [Table 1-2] [Table 1-3]

[0094] Biological Examples Seeds of various test species are sown in standard soil in pots (Amaranthus retoflexus (AMARE), Abutilon theophrasti (ABUTH), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE)). After 1 day (pre-emergence) or 8 days (post-emergence) of cultivation in a greenhouse under controlled conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity), the plants are sprayed with an aqueous spray solution obtained from a combination of the technical active ingredients in an acetone / water (50:50) solution containing 0.5% Tween 20 (polyoxyethylene sorbitan monolaurate, CAS RN9005-64-5). Unless otherwise specified, the compounds are applied at 250 g / h. The test plants are then grown in a greenhouse under controlled greenhouse conditions (24 / 16°C, day / night; 14 hours of light; 65% humidity) with watering twice a day. After 13 days, the test is evaluated for the percentage of damage caused to the plants, pre- and post-emergence. The biological activity is shown in the table below on a 5-point scale (5=80-100%; 4=60-79%; 3=40-59%; 2=20-39%; 1=0-19%).

[0095] [Table 2]

Claims

1. Formula (I): 【Chemical 1】 (In the formula, R 1 is C 1 ~C 4 Alkyl-, C 1 ~C 4 Haloalkyl-, C 1 ~C 4 Alkoxy-C 1 ~C 4 Alkyl- and C 1 ~C 4 Haloalkoxy-C 1 ~C 4 selected from the group consisting of alkyl-; R 2 is a halogen, C 1 ~C 6 Alkyl-, C 1 ~C 3 Alkoxy-, C 1 ~C 6 Haloalkyl-, C 1 ~C 3 Haloalkoxy- and -S(O) p C 1 ~C 6 selected from the group consisting of alkyl; R 3 is C 1 ~C 3 haloalkyl; R 4 is hydrogen, C 1 ~C 6 Alkyl-, C 1 ~C 6 Haloalkyl and C 3 ~C 6 cycloalkyl; R 5 is C 1 ~C 6 Alkyl, C 3 ~C 6 Cycloalkyl, C 1 ~C 6 Haloalkyl, C 1 ~C 6 -alkoxy-C 1 ~C 6 Alkyl-, C 1 ~C 6 -alkoxy-, phenyl and heteroaryl, wherein said phenyl or heteroaryl is selected from the group consisting of one, two or three R 6 may be optionally substituted by a substituent; R 6 is halogen, cyano, C 1 ~C 6 Alkyl, C 1 ~C 6 Haloalkyl- and C 1 ~C 6 independently selected from the group consisting of alkoxy-; and p is 0, 1 or 2. or an agriculturally acceptable salt thereof.

2. R 1 The compound of claim 1 , wherein is methyl.

3. R 2 is methyl, Cl, -CF 3 and -SO 2 2. The compound of claim 1, wherein the compound is selected from the group consisting of methyl.

4. R 2 The compound of claim 3 , wherein is Cl.

5. R 3 is -CF 3 or -CHF 2 2. The compound of claim 1, wherein:

6. R 4 is hydrogen or C 1 ~C 6 The compound of claim 1 which is alkyl-.

7. R 5 is C 1 ~C 6 Alkyl- or C 3 ~C 6 The compound of claim 1 which is cycloalkyl-.

8. R 5 The compound of claim 1, wherein -phenyl is optionally substituted as defined in claim 1.

9. R 5 The compound of claim 1, wherein -heteroaryl is optionally substituted as defined in claim 1.

10. R 5 is R 5a , R 5b , R 5c , R 5d , R 5e , R 5f , R 5g , R 5h , R 5i and R 5j : 【Chemistry 2】 10. The compound of claim 9, wherein the heteroaryl is selected from the group consisting of:

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

12. 12. The herbicidal composition of claim 11 further comprising at least one additional pesticide.

13. 13. The herbicidal composition of claim 12, wherein the additional pesticide is a herbicide or a herbicide safener.

14. 12. A method of controlling weeds in a propagation site, comprising applying to said propagation site a weed-controlling amount of the composition of claim 11.

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

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