Herbicidal Composition

Abstract

The present invention relates to a compound of formula (I) or an agriculturally acceptable salt thereof as component (A): TIFF2024517289000022.tif59160, and as component (B), a compound of formula (II) or an agriculturally acceptable salt thereof (II): TIFF2024517289000023.tif48160 and their use in controlling plants or inhibiting the growth of plants.

Description

[Technical field]

[0001] The present invention relates to novel herbicide combinations and their use in controlling plants or inhibiting plant growth. Herbicide compounds and compositions are known in the art. For example, WO 2015 / 084796 describes pyrrolidinone compounds for use in controlling undesirable vegetation. EP 3006444 (WO 2014 / 192936) describes heterocyclic amide herbicide compounds. WO 2020 / 215604 describes herbicide compositions comprising a trifluoromethylpyridazinol compound and a second pesticide compound. Summary of the Invention

[0002] In a first aspect of the present invention, component (A) is a compound represented by the formula (I) [ka] or an agriculturally acceptable salt thereof, and, as component (B), a compound of formula (II) [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) a method of inhibiting plant growth, and (ii) a method of controlling plants, comprising applying a herbicidally effective amount of a composition of the present invention to the plant, its part or its habitat.

[0005] In a fourth aspect, the present invention provides a method for selectively controlling grasses and / or weeds in a crop of useful plants, comprising applying to the useful plants, parts thereof or their habitat or cultivation area a herbicidally effective amount of a composition of the present invention.

[0006] In some embodiments of the method, component (A) and component (B) are applied in an amount of 0.5 to 500 g / ha.

[0007] In some examples of the method, component (A) is applied in an amount of 50 to 400 g / ha and component (B) is applied in an amount of 50 to 250 g / ha.

[0008] In a fifth aspect, the present invention provides a formulation comprising a composition of the invention comprising 0.01-90% by weight of an active agent, 0-25% of an agriculturally acceptable surfactant, and 10-99.9% of solid or liquid formulation inerts and adjuvants.

[0009] In a sixth aspect, the present invention provides a concentrated composition for dilution by the user comprising a composition of the invention comprising 2 to 80% by weight, preferably about 5 to 70% by weight, of an active agent.

[0010] In certain instances, components (A) and (B) are present in a ratio by weight of 8:1 to 1:8, 8:1 to 1:5, about 2:1, about 1.6:1, or about 1:1.

[0011] In certain instances, the compounds of formula (I) and (II) are the only herbicidally active compounds in the composition. Thus, in certain embodiments, the composition consists of component A and component B, and optionally further consists of one or more agriculturally acceptable formulation adjuvants and / or agriculturally acceptable excipients or carriers.

[0012] In a preferred embodiment, the compound of formula (I) has the formula IA: [ka] It is a stereoisomer of DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] 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, SR, Calculating synergistic and antagonistic responses of herbicide combination, 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.

[0014] 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

[0015] If the actual observed effect (O) is greater than the predicted effect (E), the effect of the combination is superadditive, 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.

[0016] The compounds of formula (I) and formula (II) are effective herbicidal compounds.

[0017] The compounds of formula (I) are described in WO 2015 / 084796.

[0018] The compound of formula (II) is described in WO 2014 / 192936.

[0019] Thus, the combinations of the present invention may utilize any additive herbicidal activity, and certain embodiments may even exhibit synergistic effects, which occurs whenever the action of the combination of active ingredients is greater than the sum of the actions of the individual ingredients.

[0020] 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.

[0021] It is also possible that the compositions of the 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.

[0022] 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 a single bond. Formulas (I) and (II) are intended to include all their 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 these possible isomeric forms and mixtures thereof.

[0023] The compounds of the compositions of the invention are typically provided in the form of an agriculturally acceptable salt, a zwitterion, or a salt of an agriculturally acceptable zwitterion. The invention encompasses all such agriculturally acceptable salts, zwitterions, and mixtures thereof in all proportions.

[0024] Suitable agriculturally acceptable salts for components (A) and (B) as 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, bicarbonate, bicarbonate, bitartrate, butyl sulfate, butyl sulfonate, butyrate, camphorate, camsylate, caprate, caproate, caprylate, carbonate, citrate, diphosphate, edetate, edisylate, enanthate, ethanedisulfonate, ethanesulfonate, ethyl sulfate, formate, fumarate, gluceptate, gluconate, glucuronate, glutamate, glycerophosphate, heptadecanoate, glycerophosphate ... anion selected from acid salt, hexadecanoate, hydrogen sulfate, 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, undecylinate, and valerate; which may be the same or different for each of components (A) and (B).

[0025] Suitable cations include, but are not limited to, metals, conjugate acids of amines, and organic cations and can be the same or different for each of components (A) and (B). 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, lysine, Examples of amines that may be used include amines such as methylamine, 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, triheptylamine, trihexylamine, triisobutylamine, triisodecylamine, 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.

[0026] The herbicides of components (A) and (B) are individually well known in the art and can be obtained commercially or prepared using methods available in the art.

[0027] Throughout this specification, the expression "composition" should be taken to mean various mixtures or combinations of components (A) and (B) when applied consecutively, i.e., one after the other within a reasonably short period of time, such as a few hours or days, for example in a single "ready-mix" form, combination spray mixtures consisting of separate formulations of a single active ingredient, such as "tank mixes", and combined use of a single active ingredient. The order of application of components (A) and (B) is not essential to the practice of the invention.

[0028] The term "herbicide" as used herein means a compound that inhibits or modifies the growth of plants. The term "herbicidally effective amount" means the amount of such a compound or combination of such compounds that can produce an inhibiting or modifying effect on the growth of plants. Inhibiting or modifying effects include any deviation from natural occurrence, such as death, delay, leaf scorch, chlorosis, shrinkage, etc.

[0029] As used herein, the term "locus" means the field in which plants are growing or in which seeds of cultivated plants are sown or in which seeds will be placed in the soil. It includes the soil, seeds and seedlings, and established vegetation.

[0030] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0031] 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.

[0032] 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, a safener protects a crop from injury by the herbicide but does not prevent the herbicide from killing weeds.

[0033] Crops of useful plants in which the compositions according to the invention can be used include perennial and annual crops, for example berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, corn (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fibre plants, such as cotton, flax, hemp, jute and sisal; agricultural crops, such as sugar and fodder beet, coffee, hops, mustard, rapeseed (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees, such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears and plums; grasses, such as bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine, and other varieties. 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, ground 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 grape.

[0034] 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, such as improved storage stability, higher nutritional value and improved flavor.

[0035] Crops should also be understood to include crops that have been made resistant 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 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 commercially available under the trade names RoundupReady® and LibertyLink®.

[0036] Crops should also be understood as those that have been made resistant to harmful insects by genetic engineering methods, such as Bt maize (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 maize is the Bt 176 maize 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 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 insecticidal 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 material 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 insecticidal Cry3 proteins.

[0037] 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 can typically be controlled include Alopecurus myosuroides, Avena fatua, Brachiaria plantaginea, Bromus, Cyperus esculentus, Digitaria sanguinalis, Echinochloa crus-galli, Lolium perenne, Lolium multiflorum, Panicum miliaceum, Poa annua, Setaria viridis, Setaria faxeri and Sorghum bicolor. Examples of dicotyledonous species which may be controlled are, 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, persica, and Xanthium strumarium.

[0038] 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.

[0039] The compositions of the present invention are particularly useful for controlling a wide variety of weeds in rice crops, especially for controlling grass, sedge and broadleaf weeds in rice crops. Examples of weeds that may be controlled by the compositions of the present invention include Echinochloas, e.g., Echinochloa phyllopogon, Echinochloa oryzoides, Echinochloa colona, ​​and Echinochloa crus-galli; Leptochloa chinensis; Digitalis, including Digitaria ciliaris and D. sanguinalis; Eleusine indica; Brachiaria (Urochloa) plantaginea; and grasses, including Ischaemum rugosum (perennial pasture grass).Further examples include the genus Sciripus, e.g., Scirpus juncoides and Scirpus murconatus; the genus Cyperus, including Cyperus iria and Cyperus difformis; Fimbristylis miliacea; and Cyperaceae, including Eleocharis kuroguwai; and Monochoria vaginalis; Eclipta prostrata; Ludwigia hyssopifolia; Sphenoclea zeylanica; Heteranthera species. sp. (limosa, reniformis, zosterifolia); Commelina sp. (diffusa, communis, benghalensis); Alisma plantago-aquatica; Sagittaria pygmaea; and broadleaf weeds including Lindernia ciliate and L dubia.

[0040] The compositions of the present invention may also be mixed with one or more further pesticides including herbicides, fungicides, insecticides, nematicides, bactericides, acaricides, 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.

[0041] Similarly, the compositions of the present invention (including those containing one or more additional pesticides described in the previous paragraph) can further contain one or more safeners. In particular, the following safeners are particularly preferred: AD 67 (MON 4660), benoxacor, cloquintocet-mexyl, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, diethrate, 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-methoxy-benzoylsulfamoyl)-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, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, as disclosed in WO 02 / 34048, a reference to fenchlorazole-ethyl also applies to fenchlorazole, etc.

[0042] The compositions of the invention can be applied before or after planting of the crop, before the weeds appear (pre-emergence application) or after the weeds appear (post-emergence application).When a safener is combined with the mixture of the invention, the mixture 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.

[0043] 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 habitat or to the post-emergence crop. The safener and the composition of the present invention can also be applied sequentially. For example, the safener can be applied before sowing the seed as a seed treatment, and the composition of the present invention can be applied to the pre-emergence habitat or to the post-emergence crop.

[0044] However, those skilled in the art will appreciate that the compositions of the present invention are particularly useful in non-selective burn down applications and may therefore also be used to control native plants or avoid crop plants, and in such situations it will be apparent that there is no need to include a safener in the compositions of the present invention.

[0045] In general, the mixing ratio (by weight) of the compound of formula (I) to the compound of formula (II) is 0.01:1 to 100:1, for example, 0.025:1 to 20:1 or 1:30 to 20:1. In certain preferred embodiments, the ratio of A:B is 8:1 to 1:8, preferably 8:1 to 1:5. In some embodiments, the ratio may be about 2:1, about 1.6:1, or about 1:1.

[0046] A preferred ratio range for A:B is 8:1 to 1:5, and one of skill in the art will recognize that the compositions may be used in any one of the following individualized ratios, for example: 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.

[0047] When applied in the compositions of the invention, component (A) is typically applied at a rate of at least 0.5 g / ha, preferably at least 1 g / ha, more preferably at least 5 g / ha, especially at a rate of 50 to 2000 g / ha, more especially 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 at least 0.05 g / ha, preferably at least 0.5 g / ha, more preferably at least 1 g / ha of component B, typically in conjunction with 5 to 2000 g / ha of component B, more particularly 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).

[0048] In certain instances, component (A) is present in an amount sufficient to apply at a rate of from 50 to 400 g / ha and component (B) is present in an amount sufficient to apply at a rate of from 50 to 250 g / ha.

[0049] 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.

[0050] The amount of the composition according to the invention to be applied depends on various factors such as the compound used; the object of treatment, e.g. plants, soil or seeds; the type of treatment, e.g. spraying, scattering or seed dressing; or the time of application. In agricultural practice, the application rate of the composition according to the invention depends on the type of effect desired and typically ranges from 55 to 4000 g of total composition per hectare, more usually from 55 to 2000 g / ha. Application is generally carried out by spraying the composition, typically over a large area by a tractor-mounted sprayer, although other methods, e.g. dusting (for dusts), drip or drench, can also be used.

[0051] The compositions of the present invention can be advantageously used in the following formulations (wherein "active ingredient" refers to the respective mixture of the compound of formula (I) and the compound of formula (II) or, if a safener is also used, to the respective mixture of the compound of formula (I) and the compound of formula (II) and the safener):

[0052] The individual components of the composition of the present invention can be utilized as technical active ingredients during manufacture. More typically, however, the composition according to the present invention can be formulated in various ways using formulation auxiliaries 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 (with water or water-miscible organic solvents as carriers), impregnated polymer film forms, or other forms known, for example, from 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 organisms, oils or solvents.

[0053] The formulations can be prepared, for example, by mixing the active ingredient with formulation adjuvants to obtain a composition in the form of a finely divided solid, granules, liquid, dispersion or emulsion. The active ingredient can also be formulated with other adjuvants, for example 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.

[0054] The active ingredient may also be contained in very fine microcapsules. Microcapsules contain the active ingredient in a porous carrier. This allows the active ingredient to be released in a controlled amount (e.g., sustained release) into the environment. Microcapsules usually have a diameter of 0.1 to 500 microns. They contain the active ingredient in an amount of about 25 to 95% by weight of the capsule weight. The active ingredient may 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 may, for example, comprise natural or synthetic rubber, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane or chemically modified polymers and starch xanthate or other polymers known to those skilled in the art. Alternatively, very fine microcapsules may be formed, in which the active ingredient is contained in the form of finely divided particles in a solid matrix of a basic substance, but the microcapsule itself is not encapsulated.

[0055] Formulation adjuvants suitable for the preparation of 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, isopropylbenzene, 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 ethyl acetate, 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.

[0056] 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.

[0057] A large number of surface-active substances can be advantageously used in both solid and liquid formulations, especially in those which can be diluted with a carrier before use. The surface-active substances can be anionic, cationic, nonionic or polymeric and can be used as emulsifying agents, wetting agents or suspending agents, or for other purposes. Typical surface-active substances 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, 1999. Further materials are described in Jersey (1981).

[0058] Further adjuvants that can be used in the agrochemical formulations include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, 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.

[0059] The formulation according to the invention may contain an additive comprising an oil of vegetable or animal origin, a mineral oil, an alkyl ester of such an oil or a mixture of such an oil and an oil derivative. The amount of oil additive in the composition according to the invention is generally 0.01-10%, 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 oils of vegetable origin, such as methyl derivatives, or oils of animal origin, such as fish oil or beef tallow. Preferred oil additives are 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 described in the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.

[0060] The formulations generally contain 0.1-99% by weight, in particular 0.1-95% by weight, of components (A) and (B) and 1-99.9% by weight of formulation adjuvants, preferably including 0-25% by weight of a surfactant. Commercial products may preferably be formulated as concentrates, but end users usually use dilute formulations.

[0061] The application rates vary within wide limits and depend 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.

[0062] Preferred formulations may have the following compositions (wt %), where the term "active ingredients" refers to the total weight % of the combination of all active ingredients in the composition.

[0063] Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1-30%, preferably 5-20% Liquid carrier: 1-80%, preferably 1-35%

[0064] Dust: Active ingredient: 0.1-10%, preferably 0.1-5% Solid carrier: 99.9-90%, preferably 99.9-99%

[0065] Suspension concentrates: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1-40%, preferably 2-30%

[0066] Wettable powder: Active ingredient: 0.5-90%, preferably 1-80% Surfactant: 0.5-20%, preferably 1-15% Solid carrier: 5-95%, preferably 15-90%

[0067] Granules: Active ingredient: 0.1-30%, preferably 0.1-15% Solid carrier: 99.5-70%, preferably 97-85%

[0068] 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. EXAMPLES

[0069] Formulation Examples

[0070] [Table 1]

[0071] 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.

[0072] [Table 2]

[0073] The combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder which can be directly used for seed treatment.

[0074] [Table 3]

[0075] Emulsions of any required dilution which can be used in plant protection can be obtained from this concentrate by dilution with water.

[0076] [Table 4]

[0077] Ready-to-use dusts can be obtained by mixing the combination with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seeds.

[0078] [Table 5]

[0079] The combination is mixed with an adjuvant, ground and the mixture is moistened with water The mixture is extruded and then dried in an air stream.

[0080] [Table 6]

[0081] The finely ground combination is applied uniformly to the kaolin moistened with polyethylene glycol in a mixer. Non-dusty coated granules are obtained in this manner.

[0082] [Table 7]

[0083] The finely ground combination is thoroughly mixed with an adjuvant to obtain 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.

[0084] [Table 8]

[0085] The finely ground combination is thoroughly mixed with an adjuvant to obtain 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 against microbial infestation.

[0086] Sustained Release Capsule Suspension 28 parts of the combination are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts defoamer and 51.6 parts water until the desired particle size is achieved. To this emulsion is added a mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. The capsule suspension formulation contains 28% active ingredient. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for that purpose.

[0087] Biological Examples Seeds of Chenopodium album (CHEAL), Ipomoea hederacea (IPOHE), Amaranthus retroflexus (AMARE), Abutilon threophrasti (ABUTH) and Stellaria media (STEME) were sown in standard sterile soil in pots. After 8 days of cultivation under controlled conditions in a greenhouse (24 / 19°C, day / night; 16 hours of light; no humidity control), the plants were sprayed with 500 l / Ha of an aqueous spray solution derived from a formulation of the technical active ingredient in a solvent and emulsifier mixture designated IF50 (11.12% Emulsogen EL360TM + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether) with a small amount of acetone to produce a 50 g / l solution, which was then diluted using 0.2% Genapol XO80 (CAS number: 9043-30-5) as an excipient to obtain the desired final dose of the test compound. When the active ingredients were applied as a mixture, an aqueous spray solution containing both active ingredients was prepared as described above. The test plants were then grown under controlled conditions in a glasshouse (24 / 18°C, day / night; 15 hours of light; 50% humidity) and watered twice a day. After 13 days, the tests were visually assessed for the percentage of phytotoxicity to the plants (where 100 = total damage to the plants; 0 = no damage to the plants) when compared to control untreated plants. Two to four replicates were applied to each treatment in a randomized block trial design.

[0088] To determine whether a mixture of active ingredients has a synergistic effect on the rate of phytotoxicity of the test plants, the Colby formula was applied: SR 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.

[0089] [Table 9]

[0090] [Table 10]

[0091] [Table 11]

[0092] [Table 12]

[0093] [Table 13]

Claims

1. As component (A), a compound represented by the formula (I) 【Chemistry 1】 or an agriculturally acceptable salt thereof, and, as component (B), a compound of formula (II) 【Chemistry 2】 or a pesticidally acceptable salt thereof.

2. 2. The composition of claim 1, wherein the weight ratio of component (A) to component (B) is from 0.01:1 to 100:1, from 0.025:1 to 20:1, or from 1:30 to 16:

1.

3. 3. The composition of claim 2, wherein the weight ratio of A:B is from 8:1 to 1:8, from 8:1 to 1:5, about 2:1, about 1.6:1, or about 1:

1.

4. The compound of formula (I) has the formula (IA): 【Chemistry 3】 The composition of claim 1 having the structure:

5. 13. An agricultural chemical composition comprising a herbicidally effective amount of the composition of claim 1.

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. 6. The composition of claim 5, further comprising an agriculturally acceptable formulation adjuvant and / or an agriculturally acceptable diluent or carrier.

10. 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 their habitat.

11. The method of claim 10, wherein component (A) is applied in an amount of 50 to 400 g / ha and component (B) is applied in an amount of 50 to 250 g / ha.

12. 11. The method of claim 10, wherein components (A) and (B) are the only herbicidally active ingredients in the composition.

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

14. 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.

15. 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, preferably about 5 to 70% by weight, of active agent.

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