Fluorinated phenylacetic acid derivatives in weed control methods

Abstract

The present invention relates to a compound of formula (I) as a herbicide. [Formula 1] TIFF2023501549000024.tif59170 (in the formula, R 1 , R 2 and n is as defined herein. The present invention further relates to agrochemically acceptable salts, herbicidal compositions comprising the compounds of formula (I), and the use of compounds of formula (I) for controlling weeds, especially in crops of useful plants.

Description

Technical Field

[0001] The present invention relates to the use of certain compounds as herbicides, herbicide compositions containing such compounds, and their use for controlling weeds in crops of useful plants or for inhibiting the growth of plants.

Background Art

[0002] Polychlorophenylacetic acids and their use as herbicides are known, for example, from GB 901553, US Patent No. 3,134,808, US Patent No. 3,218,146, and US Patent No. 3,331,865. Further, certain difluoro-containing compounds are known as intermediates in the synthesis of certain trifluoromethylpropanamides disclosed in International Publication No. 2017 / 148964. Here, it has been unexpectedly discovered that these intermediates exhibit good herbicidal properties.

Summary of the Invention

Means for Solving the Problems

[0003] Accordingly, according to the present invention, there is provided the use of a compound of formula (I)

Chemical Formula

Modes for Carrying Out the Invention

[0004] Examples of C1-C6 alkyl 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] In a preferred embodiment of the present invention, R 1 is a halogen.

[0006] Examples of halogen (or halo) include fluorine, chlorine, bromine, or iodine.

[0007] In one embodiment of the present invention, n is 1, 2, or 3, preferably 1 or 2.

[0008] In one embodiment of the present invention, when n is 1 or more, R 1 is preferably fluorine, chlorine, or bromine. More preferably, R 1 is chlorine or fluorine, and in a more preferred embodiment, R 1 is chlorine. In a particularly preferred embodiment, n is 2 and R 1 is 2,3-dichloro.

[0009] In another embodiment of the present invention, R 2 is hydrogen. In another embodiment of the present invention, R 2 is C1-C6 alkyl, preferably methyl or ethyl.

[0010] The present invention also provides an agriculturally acceptable salt of the compound of formula (I). The salt of the compound 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. In a particularly preferred embodiment, the agrochemically acceptable salt is selected from the group consisting of sodium, potassium, aluminum, dimethylamine (DMA), diglycolamine (DGA), and choline salts.

[0011] Thus, according to the present invention, formula (Ia) [Chemical formula] (wherein R 1a and R b are independently selected from the group consisting of halogen, methyl and C1-haloalkyl (preferably, CF3)) an agriculturally acceptable salt of the compound of is provided.

[0012] In a more preferred embodiment, R 1a and R b are independently selected from the group consisting of halogen, methyl and CF3.

[0013] In a more preferred embodiment, R 1a and R b are both halogen.

[0014] In a more preferred embodiment, R 1a and R b are independently selected from fluoro, chloro and bromo.

[0015] In a specific embodiment, R 1a and R 1b are both chloro.

[0016] Although the compounds of formula (I) of the present invention can be used as herbicides per se, they are generally formulated into herbicidal compositions using formulation aids such as carriers, solvents, and surfactants (SAA). Therefore, the present invention further provides a herbicidal composition comprising (i) a compound of formula (I) as defined herein (together with preferred embodiments), and (ii) 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 it 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.

[0017] The herbicidal 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 a surface-active substance.

[0018] 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).

[0019] 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 with one or more wetting agents, one or more dispersants 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).

[0020] 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 dispersants, 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).

[0021] 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 agent) from a pre-formed blank granule into a porous granular material (such as pumice, attapulgite clay, fuller's earth, kieselguhr, diatomaceous earth or ground corn cob), or by adsorbing a compound of formula (I) (or a solution thereof in a suitable agent) 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, carbohydrates and vegetable oils). One or more other additives may also be included in the granules (such as emulsifiers, wetting agents or dispersants).

[0022] 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 (e.g., to improve dilution with water or to prevent crystallization in the spray tank).

[0023] 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 dimethylamide of fatty acids C8-C 10 dimethylamide of fatty acids etc.) and chlorinated hydrocarbons. The EC product can result in an emulsion that, when water is added, emulsifies spontaneously and has sufficient stability for spray application with a suitable device.

[0024] 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 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 with low solubility in water.

[0025] 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 a solvent / SAA blend. Solvents suitable 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 such or for dilution with water to form a conventional water-in-oil emulsion.

[0026] Suspension concentrates (SC) can contain 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 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 earlier herein to yield the desired final product.

[0027] Aerosol formulations contain 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.

[0028] 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 polymer 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 polymer 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 and sustained effect of the compound.

[0029] The composition may contain one or more additives in order 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)).

[0030] The wetting agent, dispersing agent, and emulsifying agent may be cationic, anionic, amphoteric, or nonionic SAA.

[0031] Suitable cationic SAA include quaternary ammonium compounds (such as cetyltrimethylammonium bromide), imidazolines, and amine salts.

[0032] 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 pyrophosphoric acid; further, these products may be ethoxylated), sulfosuccinates, paraffin or olefin sulfonates, taurates, lignosulfonates, and phosphates / sulfates of tristyrylphenol.

[0033] Suitable amphoteric SAAs include betaines, propionates, and glycineates.

[0034] Suitable non - ionic SAAs include condensation products of alkylene oxides (such as ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof) with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or 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.

[0035] Suitable suspending agents include hydrophilic colloids (such as polysaccharides, polyvinylpyrrolidone, or sodium carboxymethylcellulose), and swelling clays (such as bentonite or attapulgite).

[0036] The herbicidal compounds of the present invention can also be used in mixtures with one or more additional herbicides and / or plant growth regulators. Examples of such additional herbicides or plant growth regulators include acetochlor, asiflufen (including asiflufen-sodium), acifluorfen, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, bilanafos, bispyribac-sodium, bixlozone, bromacil, bromoxynil, butachlor, butaphenacil, carfentrazone (including carfentrazone-ethyl), chloransulam (including chloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotoluron, chlorosulfuron, cinmethylin, clacyfos, clethodim, clodinafop (including clodinafop-propargyl), chromazone, 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, diquat dibromide, diuron, ethalfluralin, ethofumesate, fenoxaprop (including fenoxaprop-P-ethyl), fenoxasulfone, fenquinotrione, fentrazamide, flazasulfuron, florasulam, flupyradifurone (including flupyradifurone-benzyl), fluazifop (including fluazifop-P-butyl), flucarbazone (including flucarbazone-sodium), flufenacet, flumetsulam, flumioxazin, fluometuron, flupyrsulfuron (including flupyrsulfuron-methyl-sodium), fluroxypyr (including fluroxypyr-meptyl), homosafen, halosulfuron, glufosinate (including its ammonium salt),Glyphosate (including its diammonium, isopropylammonium, and potassium salts), halauxifen (including halauxifen-methyl), haloxyfop (including haloxyfop-methyl), hexazinone, hidantoin, 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, metazoxolon, metazosulfuron, metribuzin, metosulam, 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, pyridate, pyriftalid, pyrimisulfan, pyroxasulfone, pyroxasulam, cinchonazine, cinchonine, quizalofop (including quizalofop-P-ethyl and quizalofop-P-tefuryl), rimsulfuron, sulfenylsulfenyl, sethoxydim, simazine, S-metolachlor, sulfentrazone, sulfosulfuron, tebuthiuron, tefuryltrione, tembotrione, terbuthylazine, terbutryn, tetrafluoropyrimethan, thienecarbazone, thifensulfuron, thiafenox, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, tribenuron (including tribenuron-methyl), triclopyr, trifloxysulfuron (including trifloxysulfuron-sodium), triflumizoxazin, trifluralin, triflusulfuron,Ethyl 2-[[3-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]-2-pyridyl]oxy]acetate, 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-methyl-imidazolidin-2-one, 3-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione, 6-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione, 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-5-ethyl-cyclohexane-1,3-dione2-[2-(3,4-Dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-4,4,6,6-tetramethyl-cyclohexane-1,3-dione, 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5-methyl-cyclohexane-1,3-dione, 3-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]bicyclo[3.2.1]octane-2,4-dione, 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-5,5-dimethyl-cyclohexane-1,3-dione, 6-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,4,4-tetramethyl-cyclohexane-1,3,5-trione, 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]cyclohexane-1,3-dione, 4-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione, 4-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxo-pyridazine-4-carbonyl]-2,2,6,6-tetramethyl-tetrahydropyran-3,5-dione and 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).

[0037] 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.

[0038] The compounds of formula (I) can also be used in mixtures with other pesticides such as fungicides, nematicides or insecticides, examples of which are given in The Pesticide Manual.

[0039] The mixing ratio of the compound of formula (I) to the mixing partner is preferably from 1:100 to 1000:1.

[0040] This mixture can advantageously be 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).

[0041] The compounds or mixtures of the invention can also be used in combination with one or more herbicide safeners. Examples of such safeners are benoxacor, cloquintocet (including cloquintocet - mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole - ethyl), fenclorim, flurioxyphen, furilazole, isoxadifen (including isoxadifen - ethyl), mefenpyr (including mefenpyr - diethyl), metcamifene and oxabetrinil.

[0042] Particularly preferred are mixtures of the compound of formula (I) with cyprosulfamide, isoxadifen - ethyl, cloquintocet - mexyl and / or metcamifene.

[0043] The herbicide safeners of the compound of formula (I) may also be in the form of esters or salts, for example, as described in The Pesticide Manual, 16 th Edition (BCPC), 2012. The reference to cloquintocet - mexyl also applies to its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as disclosed in WO 02 / 34048.

[0044] Preferably, the mixing ratio of the compound of formula (I) to the drug injury reducing agent is 100:1 to 1:10, particularly 20:1 to 1:1.

[0045] The present invention further provides a method for controlling weeds in a place, which comprises applying to the place a composition containing an amount of the compound of formula (I) effective for controlling weeds. Further, the present invention can further provide a method for selectively controlling weeds in a place containing crop plants and weeds, which comprises applying to the place a composition of the present invention in an amount effective for controlling weeds. "Control" means killing, reducing or delaying growth, or preventing or reducing germination. It is noted that the compounds of the present invention exhibit far improved selectivity as compared with known structurally similar compounds. Generally, the plants to be controlled are unwanted plants (weeds). "Place" means an area where plants are growing or will grow. Application may be made to the place before and / or after emergence of the crop plants. A plurality of 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.

[0046] The application rate of the compound of formula I may vary within a wide range and depends on the nature of the soil, the method of application (pre-emergence or post-emergence; seed dressing; application to furrows; application to non-cultivated land, etc.), the crop plants, the weeds to be controlled, the prevailing climatic conditions, and other factors depending on the method of application, the timing of application, and the 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 more particularly 25 to 250 g / ha.

[0047] Application is typically effected by spraying the composition with a large-area sprayer mounted on a tractor, but other methods such as dusting (in the case of powders), dripping or irrigation are also possible.

[0048] Crop plants should be understood to include crop plants that have been given resistance to another herbicide or herbicide classification (e.g., ALS-, GS-, EPSPS-, PPO-, HPPD-, PDS-, and ACCase-inhibitors) by conventional breeding methods or genetic engineering. Examples of crops given resistance to imidazolinones such as imazamox by conventional breeding methods are Clearfield® summer rape (canola). Examples of crops given resistance to herbicides by recombinant DNA methods include, for example, glyphosate- and glufosinate-resistant maize varieties marketed under the trade names RoundupReady® and LibertyLink®.

[0049] Crop plants should also be understood as those to which resistance to harmful insects has been imparted 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 of NK® (Syngenta Seeds). Bt toxins are natural proteins formed by the soil bacterium Bacillus thuringiensis. Examples of toxins, or 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 have the ability to express the insecticidal Cry3 protein.

[0050] Crop plants are also understood to include those obtained by conventional breeding methods or genetic engineering and which include so-called output traits (such as improved storage stability, higher nutritional value, and improved flavor).

[0051] The composition can be used to control unwanted plants (collectively "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.

[0052] Some compounds of formula (I) are commercially available. The compounds of formula (I) (optionally, their agrochemically acceptable salts) can be obtained from starting materials available to those skilled in the art according to the following scheme.

[0053] Scheme 1

Chemical formula

[0054] Scheme 2

Chemical formula

[0055]

Table 1-1

Table 1-2

Table 1-3

Table 1-4

Table 1-5

Table 1-6

Table 1-7

Table 1-8

Table 1-9

Table 1-10

Table 1-11

Table 1-12

Example

[0056] Biological Example Seeds of various test species: redroot pigweed (Amaranthus retoflexus) (AMARE), ivy-leaved morning glory (Ipomoea hederacea) (IPOHE), black nightshade (Solanum nigrum) (SOLNI), perennial ryegrass (Lolium perenne) (LOLPE), barnyard grass (Echinochloa crus-galli) (ECHCG), 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 an 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%).

[0057]

Table 2

[0058]

Table 3

[0059] Under the experimental conditions outlined above, further tests are conducted to compare the herbicidal properties of the difluoro-containing compound (1.014) with the representative compound (C1) mentioned in GB901553 specification. The compound is applied at 1000 g / ha and 500 g / ha. The test is evaluated for the percentage of damage caused to the plants (% phytotoxicity).

[0060]

Table 4

[0061]

Table 5

[0062] The test results indicate that the difluoro-containing compound unexpectedly exhibits improved herbicidal activity against various problematic weed species at various application rates under the same conditions. Another aspect of the present invention may be as follows. 〔1〕Use of a compound of formula (I)

Chemical formula

Chemical formula

Claims

1. Use of a compound of formula (I) as a herbicide 【Chemical Formula 1】 wherein R 1 is selected from the group consisting of halogen, methyl, and C 1 -haloalkyl; R 2 is hydrogen or C 1 to C 6 alkyl; n = 0, 1, 2, 3, 4 or 5 or an agriculturally acceptable salt of said compound.

2. In the compound of formula (I), R 1 The use according to claim 1, wherein is halogen.

3. R 1 The use according to claim 2, wherein R is chlorine.

4. Use according to claim 2 or claim 3, wherein n is 2 or 3.

5. n is 2, and R 1 is 2,3-dichloro, the use according to claim 4.

6. R 2 Use according to any one of claims 1 to 5, wherein R is hydrogen.

7. R 2 Use according to any one of claims 1 to 5, wherein R is methyl or ethyl.

8. An agriculturally acceptable salt of a compound of formula (Ia) 【Chemical 2】 wherein R 1a and R b are each independently selected from the group consisting of halogen, methyl, and C 1 -haloalkyl).

9. R 1a and R 1b both being chloro, the agrochemically acceptable salt according to claim 8.

10. The agriculturally acceptable salt according to claim 8 or claim 9, wherein the salt is selected from the group consisting of salts of sodium, potassium, aluminum, dimethylamine, diglycolamine, and choline.

11. A herbicide composition comprising (i) a compound of formula (I) according to any one of claims 1 to 7 or an agriculturally acceptable salt of said compound, or an agriculturally acceptable salt according to any one of claims 8 to 10, and (ii) an agriculturally acceptable formulation adjuvant.

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

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

14. A method for controlling weeds at a location, comprising applying to the location an amount of a compound of formula (I) according to any one of claims 1 to 7 or an agriculturally acceptable salt of said compound, an agriculturally acceptable salt according to any one of claims 8 to 10, or a herbicide composition according to any one of claims 11 to 13 effective to control the weeds.

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