Mixtures of pyrimidines as herbicidal compositions

Abstract

The present invention comprises, as component (A), at least one compound of formula (I) TIFF2023545842000030.tif32170 (Wherein R1 is (II) or (III) TIFF2023545842000031.tif42138 or a pesticide-stable salt thereof, and as component (B), BI, B-II, B-III, B-IV, BV, B-VI, B-VII, B-VIII, B-IX JPEG2023545842000032.jpg137160, or an agriculturally acceptable salt thereof, and its use in controlling plants or inhibiting plant growth.

Description

[Technical Field]

[0001] The present invention relates to novel herbicidal combinations and their use in controlling plants or inhibiting plant growth. Summary of the Invention [Means for solving the problem]

[0002] In a first aspect of the present invention, as component (A), at least one compound of formula (I): [ka] (Wherein R1 is [ka] is) or a pesticidally acceptable salt thereof, and as component (B), the following: [ka] or a pesticidally acceptable salt thereof.

[0003] In a second aspect, the present invention provides the use of a composition of the invention as a herbicide.

[0004] In a third aspect, the present invention provides (i) methods for inhibiting plant growth, and (ii) methods for controlling plants, which methods comprise applying a herbicidally effective amount of a composition of the present invention to a plant, a part thereof, or a site thereof.

[0005] In a fourth aspect, the present invention provides a method for selectively controlling grasses and / or weeds in a crop of useful plants, which method comprises applying to the useful plants, parts or portions thereof or cultivated areas a herbicidally effective amount of a composition of the present invention.

[0006] In a fifth aspect, the present invention provides a formulation comprising a composition of the invention comprising 0.01 to 90% by weight of an active agent, 0 to 25% of an agriculturally acceptable surfactant, and 10 to 99.9% of solid or liquid formulation inert materials and adjuvants.

[0007] In a sixth aspect, the present invention provides a concentrated composition for dilution by the user comprising a composition of the present invention comprising 2 to 80% by weight, preferably about 5 to 70% by weight, of an active agent.

[0008] When active ingredients are combined, the expected activity (E) for any given active ingredient combination can be calculated according to the so-called Colby formula as follows (Colby, S.R., Calculating synergistic and antagonistic responses of herbicide combinations, Weeds, Vol. 15, pp. 20-22; 1967): ppm = mg / L of active ingredient (ai) X = % effect of the first active ingredient using p ppm of active ingredient Y = % effect of the second active ingredient using q ppm of active ingredient.

[0009] According to Colby, the predicted effect of active ingredients A+B using p+q ppm of active ingredients is given by the following formula:

number

[0010] If the actual observed effect (O) is greater than the predicted effect (E), the effect of the combination is supra-additive, i.e., synergistic. Mathematically, synergy corresponds to a positive value of the difference (OE). In the case of a purely complementary addition of activity (predicted activity), the difference (OE) is 0. A negative value of the difference (OE) indicates a loss of activity compared to the predicted activity.

[0011] Compounds of formula (I) have the structure AI or A-II: [ka] It has.

[0012] The compounds of formulae AI and A-II; and the compounds of formulae BI through B-IX are all effective herbicidal compounds.

[0013] Compounds of formula AI are described in WO 2015 / 108779. Compounds of formula A-II are described in WO 2016 / 196606.

[0014] Compound BI is described in U.S. Patent Application Publication No. 2012 / 019055. Compound B-II is described in WO 2013 / 176282. Compound B-III is described in WO 2016 / 196593. Compound B-IV is described in WO 2010 / 126989. Compound BV is described in EP 1 122 244. Compounds B-VI and B-VII are described in U.S. Patent Application Publication No. 2014 / 274695. Compounds B-VIII and B-IX are described in WO 2018 / 208582. DETAILED DESCRIPTION OF THE INVENTION

[0015] Thus, the combinations of the present invention may utilize any additive herbicidal activity, and certain embodiments may even exhibit synergistic effects, which occur whenever the action of the combination of active ingredients is greater than the sum of the actions of the individual ingredients.

[0016] The combinations of the present invention may also provide an expanded spectrum of activity compared to the activity provided by each individual component to mediate effective herbicidal activity and / or may allow the use of lower rates of the individual components when used in combination than when used alone.

[0017] Furthermore, it is possible that the compositions of the present invention may exhibit increased crop resistance when compared to the effect of component (A) or component (B) alone. This occurs when the action of the combination of active ingredients is less damaging to useful crops than the action of one of the active ingredients alone.

[0018] The presence of one or more possible asymmetric carbon atoms in the compounds of components (A) and (B) means that the compounds can occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Atropisomers can also occur as a result of restricted rotation around single bonds. Formulas (I) and B1-B1-IX are intended to include all possible isomeric forms and mixtures thereof. The present invention includes all possible isomeric forms and mixtures thereof. Similarly, the above formulas are intended to include all possible tautomers, if present (including lactam-lactim tautomers and keto-enol tautomers). The present invention includes all possible tautomeric forms of the compounds. The present invention includes all possible isomeric forms and mixtures thereof.

[0019] The compounds of the compositions of the present invention are typically provided in the form of agriculturally acceptable salts, zwitterions, or salts of agriculturally acceptable zwitterions. The present invention encompasses all such agriculturally acceptable salts, zwitterions, and mixtures thereof in all proportions.

[0020] Agriculturally acceptable salts suitable for components (A) and (B) used in the present invention include, but are not limited to, chloride, bromide, iodide, fluoride, 2-naphthalenesulfonate, acetate, adipate, methoxide, ethoxide, propoxide, butoxide, aspartate, benzenesulfonate, benzoate, bicarbonate, bisulfate, bitartrate, butyl sulfate, butylsulfonate, butyrate, camphorate, camsylate, caprate, caproate, caprylate, carbonate, citrate, diphosphate, edetate, edisylate, enanthate, ethanedisulfonate, ethanesulfonate, ethyl sulfate, formate, fumarate, gluceptate, gluconate, gluconate, glutamate, glycerophosphate, heptadecanoate, and anions selected from hexadecanoate, bisulfate, hydroxide, hydroxynaphthoate, isethionate, lactate, lactobionate, laurate, malate, maleate, mandelate, mesylate, methanedisulfonate, methylsulfate, mucate, myristate, napsylate, nitrate, nonadecanoate, octadecanoate, oxalate, pelargonate, pentadecanoate, pentafluoropropionate, perchlorate, phosphate, propionate, propylsulfate, propylsulfonate, succinate, sulfate, tartrate, tosylate, tridecylate, triflate, trifluoroacetate, undecylate, and valerate; components (A) and (B) may be the same or different.

[0021] Suitable cations include, but are not limited to, metals, conjugate acids of amines, and organic cations, and components (A) and (B) may be the same or different. Examples of suitable metals include aluminum, calcium, cesium, copper, lithium, magnesium, manganese, potassium, sodium, iron, and zinc.Examples of suitable amines include allylamine, ammonia, amylamine, arginine, benethamine, benzathine, butenyl-2-amine, butylamine, butylethanolamine, cyclohexylamine, decylamine, diamylamine, dibutylamine, diethanolamine, diethylamine, diethylenetriamine, diheptylamine, dihexylamine, diisoamylamine, diisopropylamine, dimethylamine, dioctylamine, dipropanolamine, dipropargylamine, dipropylamine, dodecylamine, ethanolamine, ethylamine, ethylbutylamine, ethylenediamine, ethylheptylamine, ethyloctylamine, ethylpropanolamine, heptadecylamine, heptylamine, hexadecylamine, hexenyl-2-amine, hexylamine, hexylheptylamine, hexyloctylamine, histidine, indoline, isoamylamine, isobutanolamine, isobutylamine, isopropanolamine, isopropylamine, Propylamine, lysine, meglumine, methoxyethylamine, methylamine, methylbutylamine, methylethylamine, methylhexylamine, methylisopropylamine, methylnonylamine, methyloctadecylamine, methylpentadecylamine, morpholine, N,N-diethylethanolamine, N-methylpiperazine, nonylamine, octadecylamine, octylamine, oleylamine, pentadecylamine, pentenyl-2-amine, phenoxyethylamine, picoline, piperazine, piperidine, propanolamine, propylamine, propylenediamine, pyridine, pyrrolidine, sec-butylamine, stearylamine, tallowamine, tetradecylamine, tributylamine, tridecylamine, trimethylamine, trihexylamine, triisobutylamine, triisopropylamine, trimethylamine, tripentylamine, tripropylamine, tris(hydroxymethyl)aminomethane, and undecylamine.Examples of suitable organic cations include benzyltributylammonium, benzyltrimethylammonium, benzyltriphenylphosphonium, choline, tetrabutylammonium, tetrabutylphosphonium, tetraethylammonium, tetraethylphosphonium, tetramethylammonium, tetramethylphosphonium, tetrapropylammonium, tetrapropylphosphonium, tributylsulfonium, tributylsulfoxonium, triethylsulfonium, triethylsulfoxonium, trimethylsulfonium, trimethylsulfoxonium, tripropylsulfonium, and tripropylsulfoxonium.

[0022] The herbicides of components (A) and (B) are well known in the art and can be obtained commercially or prepared using methods available in the art. Table 1 lists specific combinations of components (A) and (B) according to the present invention.

[0023] [Table 1]

[0024] Throughout this specification, the expression "composition" should be taken to mean various mixtures or combinations of components (A) and (B) when applied sequentially, i.e., one after the other within a reasonably short period of time, such as a few hours or days, e.g., in a single "ready-mix" form, combination spray mixtures composed of separate formulations of a single active ingredient such as "tank mixes," and combined uses of a single active ingredient. The order in which components (A) and (B) are applied is not essential to the practice of the invention.

[0025] As used herein, the term "herbicide" refers to a compound that inhibits or modifies plant growth. The term "herbicidally effective amount" refers to the amount of such a compound or combination of such compounds that is capable of producing an inhibiting or modifying effect on plant growth. Inhibiting or modifying effects include any deviation from natural occurrence, such as death, delay, leaf scorch, chlorosis, dwarfism, etc.

[0026] As used herein, the term "site" means the field where plants are growing or where seeds of cultivated plants have been sown or where seeds will be placed in the soil, including the soil, seeds and seedlings, and established vegetation.

[0027] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0028] The term "plant propagation material" refers to all reproductive parts of plants, such as seeds or vegetative parts of plants, such as cuttings and tubers. This includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes and plant parts.

[0029] As used herein, the term "safener" means a chemical that, when used in combination with a herbicide, reduces the undesirable effects of the herbicide on non-target organisms; for example, the safener protects crops from herbicide injury but does not prevent the herbicide from killing weeds.

[0030] Crops of useful plants in which the compositions according to the invention can be used include perennial and annual crops, such as berry plants, for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals, for example barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example cotton, flax, hemp, jute and sisal; field crops, for example sugar and fodder beet, coffee, hops, mustard, rapeseed (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, for example apple, apricot, avocado, banana, cherry, citrus fruit, nectarine, peach, pear and plum; grasses, for example bermudagrass, bluegrass, bentgrass, centipedegrass, fescue, ryegrass, St. Augustine. herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage, thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, crushed nuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olives and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, mallow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; grapes such as grapes.

[0031] Crops are to be understood as those occurring in nature, those obtained by traditional breeding methods, or those obtained by genetic engineering, including crops that contain so-called output traits (e.g., improved storage stability, higher nutritional value, and improved flavor).

[0032] Crops should also be understood to include crops that have been made tolerant to herbicides or classes of herbicides (e.g., ALS inhibitors, GS inhibitors, EPSPS inhibitors, PPO inhibitors, ACCase inhibitors, and HPPD inhibitors) by conventional breeding methods or genetic engineering. An example of a crop that has been made tolerant to imidazolinones, such as imazamox, by conventional breeding methods is Clearfield® summer rapeseed (canola). Examples of crops that have been made tolerant to herbicides by genetic engineering methods include, for example, glyphosate-resistant and glufosinate-resistant corn varieties commercially available under the trade names RoundupReady® and LibertyLink®.

[0033] Crops are also understood to be those that have been made resistant to harmful insects by genetic engineering methods, such as Bt corn (resistant to the European corn borer), Bt cotton (resistant to the boll weevil), and Bt potato (resistant to the Colorado beetle). An example of Bt corn is the Bt 176 corn hybrid from NK® (Syngenta Seeds). Bt toxins are proteins naturally produced by the soil bacterium Bacillus thuringiensis. Examples of toxins, or transgenic 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 transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are KnockOut® (corn), Yield Gard® (corn), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potato), NatureGard®, and Protexcta®. Plant crops or their seed materials can be resistant to herbicides and insect feeding at the same time (a "stacked" transgenic event). For example, seeds can be resistant to glyphosate while having the ability to express an insecticidal Cry3 protein.

[0034] The compositions of the present invention can typically be used to control a wide variety of monocotyledonous and dicotyledonous weed species. Examples of monocotyledonous species that may typically be controlled include Alopecurus myosuroides, oat (Avena fatua), Brachiaria plantaginea, bromegrass (Bromus), corngrass (Cyperus esculentus), large crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crus-galli), ryegrass (Lolium perenne), loosegrass (Lolium multiflorum), millet (Panicum miliaceum), annual bluegrass (Poa annua), foxtail (Setaria viridis), foxtail (Setaria faberi) and sorghum (Sorghum bicolor). Examples of dicotyledonous species that may be controlled include, for example, Abutilon theophrasti, Amaranthus retroflexus, Bidens pilosa, Chenopodium album, Euphorbia heterophylla, Galium aparine, Ipomoea hederacea, Kochia scoparia, Polygonum convolvulus, Sida spinosa, Sinapis arvensis, Solanum nigrum, Stellaria media, Veronica persica, and the like. persica, and Xanthium strumarium.

[0035] In all aspects of the invention, in any particular embodiment, for example, the weeds to be controlled and / or stunted may be monocotyledonous or dicotyledonous weeds that are tolerant or resistant to one or more other herbicides, for example, HPPD inhibitor herbicides such as mesotrione, PSII inhibitor herbicides such as atrazine, or EPSPS inhibitors such as glyphosate. Such weeds include, but are not limited to, resistant Amaranthus biotypes.

[0036] The compositions of the present invention may also be mixed with one or more additional pesticides including herbicides, fungicides, insecticides, nematicides, bactericides, miticides, growth regulators, chemical sterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds different from the herbicide of formula (I) and the herbicide of component (B) to form multi-component pesticides which provide even broader agricultural protection.

[0037] Similarly, compositions of the present invention (including those containing one or more additional pesticides described in the previous paragraph) can further include one or more safeners. Specifically, the following safeners are particularly preferred: AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole-ethyl, fenchlorin, flurazole, fluxofenim, furilazole, furilasome, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, oxabetrinil, naphthalic anhydride (CAS RN 81-84-5), TI-35, N-isopropyl-4-(2-methoxybenzoylsulfamoyl)-benzamide (CAS RN 221668-34-4), and N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide. Such safeners may also be used in the form of esters or salts, as described, for example, in The Pesticide Manual, 15th Ed. (BCPC), 2009. Thus, a reference to cloquintocet-mexyl also applies to cloquintocet as well as its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as disclosed in WO 02 / 34048, a reference to fenchlorazole-ethyl also applies to fenchlorazole, etc.

[0038] The compositions of the present invention can be applied before or after planting of the crop, before weeds appear (pre-emergence application) or after weeds appear (post-emergence application). When a safener is combined with the mixture of the present invention, the mixing ratio of the compound of formula (I) to the safener is preferably from 100:1 to 1:10, in particular from 20:1 to 1:1.

[0039] The safener and the composition of the present invention can be applied simultaneously. For example, the safener and the composition of the present invention can be applied to the pre-emergence site or to the crop after emergence. Alternatively, the safener and the composition of the present invention can be applied sequentially. For example, the safener can be applied as a seed treatment before sowing the seeds, and the composition of the present invention can be applied to the pre-emergence site or to the crop after emergence.

[0040] However, those skilled in the art will appreciate that the compositions of the present invention are particularly useful in non-selective burndown applications and may therefore also be used to control volunteer plants or avoid crop plants, and in such situations it will be apparent that the inclusion of a safener in the compositions of the present invention is not necessary.

[0041] Generally, the mixing ratio (by weight) of the compound of formula (I) to the compound of component B is 0.01:1 to 100:1, more preferably 0.025:1 to 20:1, and even more preferably 1:30 to 20:1. Accordingly, the preferred ratio ranges for the preferred compositions of the present invention are shown in Table 2 below.

[0042] [Table 2]

[0043] Those skilled in the art will understand that the most preferred ratio range of A:B for any one of composition numbers 1.001-1.018 listed in Table 2 above is 1:30-20:1, and that each of composition numbers 1.001-1.018 listed in Table 2 above can be used in any one of the following individualized ratios: 1:30, 1:15, 2:15, 3:20, 1:6, 1:5, 1:4, 4:15, 3:10, 1:3, 5:14, 3:8, 2:5, 8:15, 3:5, 5:7, 3:4, 4:5, 1:2, 1:1, 16:15, 6:5, 4:3, 10:7, 3:2, 8:5, 5:3, 2:1, 12:5, 8:3, 20:7, 16:5, 10:3, 4:1, 8:1, 12:1, and 16:1.

[0044] When applied in the compositions of the present invention, component (A) is typically applied at a rate of 50 to 2000 g / ha, more specifically 50, 75, 100, 125, 150, 200, 250, 300, 400, 500, 750, 800, 1000, 1250, 1500, 1800, or 2000 g / ha. Such rates of component (A) are typically applied in conjunction with 5 to 2000 g / ha of component B, more specifically 5, 10, 15, 20, 25, 50, 75, 100, 125, 140, 150, 200, 250, 300, 400, 500, 750, 1000, 1250, 1500, 1800, or 2000 g / ha of component (B). The examples described herein illustrate, but do not limit, the ranges of ratios of components (A) and (B) that may be used in the present invention.

[0045] The amount of the composition according to the present invention to be applied depends on various factors, such as the compound used; the target of treatment, e.g., plants, soil, or seeds; the type of treatment, e.g., spraying, dusting, or seed dressing; and the time of application. In agricultural practice, the application rate of the composition according to the present invention depends on the type of desired effect and is typically in the range of 55 to 4000 g of total composition per hectare, more commonly 55 to 2000 g / ha. Application is generally carried out by spraying the composition, typically over a wide area with a tractor-mounted sprayer, although other methods, such as dusting (for dusting), dripping, or drench application, can also be used.

[0046] The compositions of the present invention can be advantageously used in the following formulations (where "active ingredient" refers to the respective mixture of the compound of formula (I) and the compound of component B, or, if a safener is also used, the respective mixture of the compound of formula (I), the compound of component B and the safener):

[0047] The individual components of the compositions of the present invention can be utilized as technical active ingredients during production. However, more typically, compositions according to the present invention can be formulated in various ways using formulation aids such as carriers, solvents, and surfactants. The formulations can be in various physical forms, such as powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, oil flowables, water dispersions, oil dispersions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (using water or a water-miscible organic solvent as a carrier), impregnated polymer film forms, or other forms known from, for example, the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can be used directly or diluted before use. Dilution can be carried out, for example, with water, liquid fertilizers, micronutrients, biological materials, oils, or solvents.

[0048] The formulations can be prepared by mixing the active ingredient with formulation adjuvants to obtain compositions in the form of, for example, finely divided solids, granules, solutions, dispersions or emulsions. The active ingredient can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surfactants or combinations thereof.

[0049] The active ingredient can also be contained in very fine microcapsules. Microcapsules contain the active ingredient in a porous carrier, allowing for controlled (e.g., sustained) release of the active ingredient into the environment. Microcapsules typically have diameters of 0.1 to 500 microns. They contain the active ingredient in an amount of about 25 to 95% by weight of the capsule. The active ingredient can be in the form of a monolithic solid, in the form of microparticles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulating membrane can comprise, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane, or chemically modified polymers, including starch xanthate, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of a base material, but the microcapsules themselves are not encapsulated.

[0050] Formulation adjuvants suitable for preparing the compositions according to the invention are known per se. Liquid carriers include water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abiet, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid Examples of suitable solvents include methyl alcohol, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone.

[0051] Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar materials.

[0052] Many surfactants can be advantageously used in both solid and liquid formulations, especially those that can be diluted with a carrier before use. The surfactants can be anionic, cationic, nonionic or polymeric and can be used as emulsifying agents, wetting agents or suspending agents, or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylaryl sulfonates, such as calcium dodecylbenzene sulfonate; alkylphenol / alkylene oxide adducts, such as nonylphenol ethoxylate; alcohol / alkylene oxide adducts, such as tridecyl alcohol ethoxylate; soaps, such as sodium stearate; alkylnaphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters; also see, for example, McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood, New York, NY Further substances are mentioned in Jersey (1981).

[0053] Further adjuvants that can be used in pesticide formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, antifoaming agents, complexing agents, neutralizing or pH adjusting substances and buffers, corrosion inhibitors, fragrances, wetting agents, uptake promoters, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreeze agents, fungicides and liquid and solid fertilizers.

[0054] The formulations according to the present invention may contain additives including vegetable or animal-derived oils, mineral oils, alkyl esters of such oils, or mixtures of such oils with oil derivatives. The amount of oil additive in the compositions according to the present invention is generally 0.01 to 10% based on the mixture to be applied. For example, the oil additive can be added to the spray tank at the desired concentration after the spray mixture is prepared. Preferred oil additives include mineral oils or oils of vegetable origin, such as rapeseed oil, olive oil, or sunflower oil, emulsified vegetable oils, alkyl esters of vegetable oils, such as methyl derivatives, or oils of animal origin, such as fish oil or beef tallow. Preferred oil additives include C8C 22 Alkyl esters of fatty acids, especially C 12 ~C 18 Methyl derivatives of fatty acids, such as the methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are listed in the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.

[0055] The formulations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds (A) and (B) and 1 to 99.9% by weight of formulation adjuvants, preferably including 0 to 25% by weight of surfactants. Commercial products are preferably formulated as concentrates, although end users usually use diluted formulations.

[0056] The application rate varies within wide limits and depends on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. As a general guideline, the compounds can be applied at a rate of 1 to 2000 l / ha, in particular 10 to 1000 l / ha.

[0057] Preferred formulations may have the following compositions (% by weight), where the term "active ingredients" refers to the total weight % of the combination of all active ingredients in the composition.

[0058] Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1-80%, preferably 1-35%

[0059] Dust: Active ingredient: 0.1-10%, preferably 0.1-5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0060] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30%

[0061] Wettable powder: Active ingredient: 0.5-90%, preferably 1-80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90%

[0062] Granules: Active ingredient: 0.1-30%, preferably 0.1-15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0063] Various aspects and embodiments of the invention will now be described in more detail by way of example, it being understood that modifications of detail can be made without departing from the scope of the invention. Another aspect of the present invention may be as follows. [1] As component (A), at least one compound of formula (I): [C1] JPEG0007819185000008.jpg27170 (In the formula, R 1 teeth, [C2] JPEG0007819185000009.jpg40160 is) or a pesticidally acceptable salt thereof, and as component (B), the following: [C3] JPEG0007819185000010.jpg137160 1. A composition comprising at least one compound selected from the group consisting of: [2] The composition according to [1] above, wherein the weight ratio of component (A) to component (B) is 0.01:1 to 100:1. [3] The composition according to [1] or [2] above, wherein the weight ratio of component (A) to component (B) is 0.025:1 to 20:1. [4] The composition according to any one of [1] to [3] above, wherein the weight ratio of component (A) to component (B) is 1:30 to 16:1. [5] A pesticide composition comprising a herbicidally effective amount of the composition according to any one of [1] to [4] above. [6] The composition according to [5], further comprising at least one additional active ingredient. [7] The composition according to [6], wherein the at least one additional active ingredient comprises at least one additional pesticide. [8] The composition according to [7], wherein the additional pesticide is a herbicide or a herbicide safener. [9] The composition according to any one of [5] to [8] above, further comprising an agriculturally acceptable formulation adjuvant and / or an agriculturally acceptable diluent or carrier.

[10] A method for suppressing the growth of unwanted plants, comprising applying a herbicidally effective amount of the composition according to any one of [1] to [9] to unwanted plants, parts thereof, or sites thereof.

[11] Use of the composition according to any one of [1] to [9] above as a herbicide.

[12] A formulation comprising the composition according to any one of [1] to [4] above, which comprises 0.01 to 90% by weight of an active agent, 0 to 25% by weight of an agriculturally acceptable surfactant, and 10 to 99.9% by weight of a solid or liquid formulation inactive substance and adjuvant.

[13] A concentrated composition for dilution by a user, comprising the composition according to any one of [1] to [4] above, which contains 2 to 80% by weight, preferably about 5 to 70% by weight, of an active agent. [Example]

[0064] Formulation example

[0065] [Table 3]

[0066] The combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a wettable powder which can be diluted with water to obtain a suspension of the desired concentration.

[0067] [Table 4]

[0068] The combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly for seed treatment.

[0069] [Table 5]

[0070] Emulsions of any required dilution that can be used for plant protection can be obtained from this concentrate by dilution with water.

[0071] [Table 6]

[0072] Ready-to-use dusts are obtained by mixing the combination with a carrier and grinding the mixture in a suitable mill. Such powders can also be used in dry dressings for seeds.

[0073] [Table 7]

[0074] The combination is mixed and ground with the adjuvant, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0075] [Table 8]

[0076] The finely ground combination is evenly applied to kaolin moistened with polyethylene glycol in a mixer, thus obtaining non-dusty coated granules.

[0077] [Table 9]

[0078] The finely ground combination can be thoroughly mixed with an adjuvant to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Such dilutions can be used to treat living plants and plant propagation material by spraying, pouring, or immersion to protect them from microbial infestation.

[0079] [Table 10]

[0080] The finely ground combination can be thoroughly mixed with an adjuvant to give a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Such dilutions can be used to treat living plants and plant propagation material by spraying, pouring, or immersion to protect them from microbial infestation.

[0081] Sustained-release capsule suspension 28 parts of the combination are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent, and 51.6 parts water until the desired particle size is achieved. To this emulsion, a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by the addition of 0.25 parts thickener and 3 parts dispersant. The capsule suspension formulation contains 28% active ingredient. The media capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in a device suitable for that purpose.

[0082] Biological Examples Seeds of Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Digitaria sanguinalis (DIGSA), Lolium perenne (LOLPE), Alopecurus myosuroides (ALOMY), Chenopodium album (CHEAL), Ipomoea hederacea (IPOHE), Stellaria media (STEME), Abutilon threophrasti (ABUTH), and Amaranthus retroflexus (AMARE) were sown in standard sterile soil in pots. After 8 days of incubation under controlled conditions in a greenhouse (24 / 19°C, day / night; 16 hours light; no humidity control), the plants were sprayed at 500 l / Ha with a small amount of acetone and an aqueous spray solution resulting from a formulation of the technical active ingredient in a solvent and emulsifier mixture called IF50 (11.12% Emulsogen EL360™ + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether) to make a 50 g / l solution, which was then diluted with 0.2% Genapol XO80 (CAS number: 9043-30-5) as diluent to obtain the desired final dose of the test compound.

[0083] When the active ingredients were applied as a mixture, an aqueous spray solution containing both active ingredients was prepared as described above.

[0084] Test plants were then grown under controlled conditions in a glasshouse (24 / 18°C, day / night; 15 h light; 50% humidity) and watered twice daily. After 13 days, the tests were visually assessed for percent phytotoxicity to the plants (where 100 = total plant damage; 0 = no plant damage; NC = not captured) compared to control untreated plants. Two to four replicates were applied to each treatment in a randomized block design.

[0085] The results for the individual active ingredients are shown in Table B1 below, and the results for the combination of the invention are shown in Table B2 below.

[0086] [Table 11-1] [Table 11-2]

[0087] To determine whether a mixture of active ingredients has a synergistic effect on the rate of phytotoxicity of the test plants, Colby's formula was applied: S.R. Colby (1967) "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, p. 22., E=X+Y-(X*Y / 100), where: X = average percent phytotoxicity of herbicide A when applied at a constant rate Y = average percent phytotoxicity using herbicide B when applied at a constant rate E = predicted efficacy of a mixture of herbicides A and B calculated from Colby's formula.

[0088] [Table 12-1] [Table 12-2] [Table 12-3] [Table 12-4] [Table 12-5] [Table 12-6] [Table 12-7] Table 12-8

Claims

1. Component (A) is a compound represented by the following formula (I): or a pesticidally acceptable salt thereof, and as component (B), the following:

1. A composition comprising at least one compound selected from the group consisting of:

2. 10. The composition of claim 1, wherein the weight ratio of component (A) to component (B) is from 0.01:1 to 100:

1.

3. 3. The composition of claim 1, wherein the weight ratio of component (A) to component (B) is from 0.025:1 to 20:

1.

4. The composition of any one of claims 1 to 3, wherein the weight ratio of component (A) to component (B) is from 1:30 to 16:

1.

5. A pesticide composition comprising a herbicidally effective amount of the composition of any one of claims 1 to 4.

6. 6. The composition of claim 5, further comprising at least one additional active ingredient.

7. 7. The composition of claim 6, wherein the at least one additional active ingredient comprises at least one additional pesticide.

8. 8. The composition of claim 7, wherein the additional pesticide is a herbicide or a herbicide safener.

9. The composition of any one of claims 5 to 8, further comprising an agriculturally acceptable formulation adjuvant and / or an agriculturally acceptable diluent or carrier.

10. A method for controlling the growth of unwanted plants, comprising applying a herbicidally effective amount of the composition of any one of claims 1 to 9 to the unwanted plants, parts thereof or areas thereof.

11. Use of a composition according to any one of claims 1 to 9 as a herbicide.

12. 5. A formulation comprising the composition of any one of claims 1 to 4, comprising 0.01 to 90% by weight of active agent, 0 to 25% of an agriculturally acceptable surfactant, and 10 to 99.9% of solid or liquid formulation inert substances and adjuvants.

13. A concentrated composition for dilution by the user comprising a composition according to any one of claims 1 to 4, comprising from 2 to 80% by weight of an active agent.

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