Compositions and methods for controlling weeds

Abstract

The present invention relates to a method for controlling weeds in susceptible turfgrass without causing serious damage to the susceptible turfgrass which comprises applying to the turfgrass a herbicidally effective amount of quinclorac or a salt thereof and a phytotoxicity-reducing amount of metcamifene.

Description

[Technical field]

[0001] The present invention relates to compositions and methods for controlling turfgrass weeds without causing severe damage to the turfgrass, and in particular to compositions and methods for controlling St. Augustine grass weeds without causing severe damage to the turfgrass using compositions containing a herbicidally effective amount of quinclorac and the safener metcamifen. [Background technology]

[0002] The need to remove unwanted plants and other undesirable vegetation, such as noxious weeds and invasive plants, is a recurring problem not only in agriculture, but also in landscaping and industrial fields. For example, selective removal of problematic weeds and invasive species from golf courses (greens, fairways, tees, and roughs), sports fields, industrial turfgrass, and residential turfgrass is essential to maintain high quality and healthy turfgrass. Weeds can reduce turfgrass quality due to the color and texture contrast between the turfgrass plants and the weeds. In addition, weeds compete with turfgrass plants for available water and nutrients, which usually reduces the desired turfgrass coverage. Therefore, there is a need for novel methods to control turfgrass weeds and provide high quality and healthy turfgrass.

[0003] Quinclorac (3,7-dichloro-8-quinoline carboxylic acid) (CAS RN:84087-01-4; EP 60429) is a synthetic auxinic herbicide effective for the control of certain broadleaf and grass weeds in turfgrass. See also Johnson, Journal of Environmental Horticulture (1994) 12(2):83-86. However, quinclorac is phytotoxic to certain susceptible turfgrasses. Quinclorac's phytotoxicity is particularly severe when used for weed control in certain warm-season turfgrasses.

[0004] Metocamifen (2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide) (CAS RN: 129531-12-0; U.S. Pat. No. 5,215,570) is a safener compound useful for protecting cultivated plants from the harmful effects of various selective herbicides. Certain crystalline polymorphic forms of the safener metcamifen are also known, including Form 1, Form 2, and Form 3 (WO 2013 / 117691). Summary of the Invention [Problem to be solved by the invention]

[0005] There remains a need for improved quinclorac weed control compositions and methods in synthetic auxin-sensitive turfgrass that reduce the phytotoxicity of quinclorac to such turfgrass.

[0006] Surprisingly, it has now been discovered that when quinclorac is applied in combination with metcamifene to selectively control unwanted weeds in the presence of susceptible turfgrass, the phytotoxic effects of quinclorac can be further reduced without losing herbicidal efficacy. In particular, it has been discovered that when quinclorac is applied in combination with metcamifene to selectively control certain susceptible tropical turfgrass weeds, particularly St. Augustine grass, the phytotoxic effects of quinclorac or a salt thereof can be further reduced without losing herbicidal efficacy against such weeds. [Means for solving the problem]

[0007] According to the present invention, there is provided a method for controlling weeds in susceptible turfgrass without causing serious damage to the susceptible turfgrass, which comprises applying to the turfgrass a herbicidally effective amount of quinclorac or a salt thereof and an effective amount of metcamifene as a safener.

[0008] In particular, the present invention involves selectively controlling unwanted weeds in a turfgrass habitat in the presence of susceptible warm-season (C4) turfgrass without causing significant damage to the turfgrass by applying to the turfgrass habitat a herbicidally effective amount of quinclorac or a salt thereof and an effective amount of metcamifene as a safener.

[0009] More specifically, the present invention provides a method for selectively controlling unwanted weeds in a turfgrass habitat in the presence of synthetic auxin-sensitive warm-season (C4) turfgrass without causing significant damage to the turfgrass or inhibiting herbicidal activity, the method comprising applying to the turfgrass habitat a herbicidally effective amount of quinclorac or a salt thereof and an effective amount of metcamifene as a safener.

[0010] The method of the present invention is particularly suited for selectively controlling unwanted weeds in a turfgrass habitat in the presence of St. Augustine grass without seriously damaging or inhibiting the herbicidal activity of the St. Augustine grass, and comprises applying to the turfgrass habitat a composition containing a herbicidally effective amount of quinclorac or a salt thereof and an effective amount of metcamifen as a safener.

[0011] The present invention also provides a reduced phytotoxicity herbicide composition for use on turfgrass susceptible to damage from synthetic auxin herbicides, comprising: a) a herbicidally effective amount of quinclorac or a salt thereof; and b) a reduced phytotoxicity amount of metcamifene, which composition renders the quinclorac or salt thereof safe for turfgrass.

[0012] The present invention further provides a method for reducing the phytotoxicity of a synthetic auxinic herbicide compound, such as quinclorac or a salt thereof, applied alone or in a mixture with one or more herbicide combination compounds to warm season (C4) turfgrass, such as St. Augustinegrass, comprising applying to the locus of the turfgrass an antidote-effective amount of metcamifen. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] Embodiments of the method of the present invention are provided as follows.

[0014] In one embodiment, quinclorac (3,7-dichloro-8-quinolinecarboxylic acid) is applied or formulated in its acid form.

[0015] In another embodiment, quinclorac (3,7-dichloro-8-quinoline carboxylic acid) may be applied or formulated as a salt, such as the dimethylamine salt. Unless otherwise specified, references herein to quinclorac are understood to mean quinclorac acid or a salt thereof.

[0016] In one embodiment, the reduced phytotoxicity herbicide composition of the present invention is suitable for use on turfgrass that is susceptible to damage from synthetic auxinic herbicides such as quinclorac. The composition contains: a) a herbicidally effective amount of quinclorac or a salt thereof; and b) a safening effective amount of metcamifen. The reduced phytotoxicity herbicide composition of the present invention can make quinclorac or a salt thereof safe for turfgrass.

[0017] In one embodiment, the reduced phytotoxicity herbicide composition comprises an aqueous application composition.

[0018] In another embodiment, the weight ratio of (a) quinclorac to (b) metcamifene in the reduced phytotoxicity herbicide compositions and methods is from 1:2 to 450:1, more particularly from 2:1 to 45:1, preferably from 35:1 to 3:1. In a preferred embodiment, the weight ratio of (a) quinclorac to (b) metcamifene in the reduced phytotoxicity herbicide compositions and methods is 573:75, or 7.64:1.

[0019] In one embodiment, a herbicidally effective amount of quinclorac is applied to the turfgrass at a rate of 140-2240 g ai / ha, more specifically 280-1120 g ai / ha, preferably 400-850 g ai / ha. When quinclorac is applied as a salt, the application rates of the herbicidally effective amounts of quinclorac described above can be expressed as acid equivalents (ae) per hectare.

[0020] In one embodiment, metcamifen as (2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide) is used as the safener in the compositions or methods of the invention.

[0021] In another embodiment, metcamifene can be applied or formulated as a crystalline polymorph designated Form 1 as described in WO 2013 / 117691, characterized, for example, by a powder X-ray diffraction pattern expressed in 2θ angles, the powder X-ray diffraction pattern including at least three, at least four, at least five, at least six, at least seven, or all 2θ angle values ​​(in degrees) selected from the group including: 7.4±0.2, 9.3±0.2, 11.7±0.2, 12.0±0.2, 14.3±0.2, 15.1±0.2, 17.4±0.2, and 19.0±0.2. Form 1 has a melting point of 198°C±5°C. This melting point is obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0022] In another embodiment, metcamifene may be applied or formulated as a crystalline polymorph designated Form 2 as described in WO 2013 / 117691, characterized by a powder X-ray diffraction pattern expressed in 2θ angles, comprising at least one 2θ angle value of 9.0±0.2, one 2θ angle value of 21.7±0.2, and at least three, at least four, at least five, at least six, or all 2θ angle values ​​selected from the group comprising 7.7±0.2, 11.9±0.2, 13.4±0.2, 15.0±0.2, 15.6±0.2, 16.1±0.2, and 18.0±0.2. Form 2 has a melting point of 216°C±5°C. This melting point is obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0023] In another embodiment, metcamifene may be applied or formulated as the crystalline polymorph designated Form 3 described in WO 2013 / 117691, which is characterized by an X-ray powder diffraction pattern, expressed in 2θ angles, comprising one 2θ angle value of 16.9±0.2, one 2θ angle value of 18.9±0.2, and at least three, at least four, at least five, at least six, at least seven, at least eight, at least nine, at least ten, or all 2θ angle values ​​selected from the group comprising: 7.5±0.2, 12.3±0.2, 13.4±0.2, 14.4±0.2, 14.9±0.2, 15.8±0.2, 18.3±0.2, 20.9±0.2, 21.9±0.2, 22.6±0.2, and 23.8±0.2. Form 3 has a melting point of 202° C.±5° C. This melting point is obtained using Differential Scanning Calorimetry (DSC) at a heating rate of 10° C. / min.

[0024] Unless otherwise specified, references herein to metcamifene are understood to mean metcamifene as (2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide) or its polymorphs (Form 1, Form 2, or Form 3).

[0025] In one embodiment, the effective amount of metcamifene is a safening or antidote effective amount. Preferably, the safening or antidote effective amount of metcamifene applied to turfgrass in accordance with the present invention is at a rate of 5-300 g ai / ha, more specifically at a rate of 25-150 g ai / ha.

[0026] In one embodiment, the method of the present invention involves applying a herbicidally effective amount of quinclorac or a salt thereof and a safening effective amount of metcamifen to the turfgrass locus either simultaneously or sequentially. In a preferred embodiment, quinclorac or a salt thereof and metcamifen are applied to the turfgrass locus simultaneously, preferably with a safened herbicide composition of the present invention.

[0027] Preferably, in the method of the present invention, quinclorac or a salt thereof and metcamifen are applied simultaneously or sequentially to the turfgrass habitat by post-emergence foliar treatment. More preferably, quinclorac or a salt thereof and metcamifen are applied simultaneously to the turfgrass habitat by post-emergence foliar treatment using an aqueous spray composition.

[0028] In one embodiment, quinclorac or its salt and metcamifen are applied to the turfgrass habitat in an aqueous spray composition. In another embodiment, the amount of aqueous spray solution applied to the turfgrass habitat is 100-300 l / ha. Preferably, the amount of water of the aqueous spray composition applied to the turfgrass habitat is 150-200 l / ha, for example 187 l / ha.

[0029] In one embodiment, one to three subsequent sequential foliar applications of quinclorac or a salt thereof and metcamifen are applied to the turfgrass habitat on a 7 to 42 day application schedule or interval, preferably at 14 to 21 day intervals.

[0030] In one embodiment, the method of the present invention applies a herbicidally effective amount of quinclorac or its salts and an effective amount of metcamifen as a safener to a turfgrass habitat that contains unwanted broadleaf or grass weeds to be controlled and desirable synthetic auxin (quinclorac) sensitive warm-season (C4) turfgrass species (such as St. Augustine grass). For example, the term "turfgrass habitat" refers to an area where both broadleaf or grass weeds and desirable synthetic auxin sensitive warm-season (C4) turfgrass species are germinated, grown, or established, such as golf courses (greens, fairways, tees, and roughs), sports fields, industrial turfgrass, residential turfgrass, recreational grasslands or sites, grasslands or turfgrass around airports, cemeteries, commercial facilities and rights-of-way, places of worship, military installations and other facilities, apartment complexes, parks, picnic areas, roadsides, schools, turf farms, etc. In the context of the present invention, turfgrass habitats may further include other types of plants, weeds, or vegetation, however, the present invention relates to methods of controlling unwanted weeds (broadleaf or grass weeds) in such habitats, including emerged, growing, and established vegetation.

[0031] The term "susceptible" refers to turfgrass species that may suffer phytotoxic damage from application of synthetic auxin (quinclorac) in the absence of metcamifen. For example, damage, particularly severe or excessive damage, means unacceptable levels of phytotoxicity, turfgrass chlorosis or stunted growth, and / or unacceptable reduction in turfgrass color and quality. Turfgrass color and quality is an industry standard rating based on a scale of 1 to 9, with 9 indicating a dark green color and the best quality of turfgrass. Turfgrass quality is based on multiple factors, including stunted growth, uniformity of turfgrass population, and density. Turfgrass quality of 6 or below is considered unacceptable.

[0032] Thus, a method of reducing phytotoxicity to warm season (C4) turfgrass, such as St. Augustinegrass, by application of a synthetic auxinic herbicide compound, such as quinclorac or a salt thereof, alone or in a mixture with one or more herbicide combination compounds, comprises applying to the turfgrass habitat an antidote-effective amount of metcamifen.

[0033] Advantageously, in the practice of the invention, a herbicide combination comprising quinclorac or a salt thereof and a safener that is metcamifen is applied to selectively control weeds in turfgrass. Preferably, the combination comprises a herbicidally effective amount of quinclorac and a safening effective amount of metcamifen. The turfgrass is a synthetic auxin (quinclorac) sensitive warm season (C4) turfgrass species, such as St. Augustine grass. The selective weed control method in such turfgrass reduces phytotoxic / herbicide damage to the sensitive turfgrass without reducing or inhibiting the herbicidal activity of quinclorac on the target weeds. The weeds to be controlled are broadleaf weeds or grass weeds. Preferably, the weeds to be controlled are crabgrass, such as blanket crabgrass (Digitaria serotina), and bighorn.

[0034] In a preferred embodiment of the present invention, a method for selectively controlling unwanted broadleaf or grass weeds in a turfgrass habitat in the presence of a synthetic auxin (quinclorac) sensitive warm-season (C4) turfgrass species (such as St. Augustine grass) comprises applying to the turfgrass habitat an amount of an aqueous spray composition for controlling broadleaf or grass weeds, the composition comprising a herbicidally effective amount of quinclorac or a salt thereof and an effective amount of metcamifen as a safener, the quinclorac being applied to the turfgrass habitat at a rate of 140-2240 g ai / ha, more specifically at a rate of 280-1120 g ai / ha, preferably at a rate of 400-850 g ai / ha. When a salt of quinclorac is used, it is applied at a rate of 140-2240 g ae / ha, more specifically at a rate of 280-1120 g ae / ha, preferably at a rate of 400-850 g ae / ha.

[0035] Suitable weight ratios of quinclorac and metcamifene compounds can be found, for example, by the application rates described above for each compound. In one embodiment, the mixing ratio of quinclorac (Q) to metcamifene (M) compounds according to the invention in the method of the invention is, for example, 280:75 to 1120:75, or 10:1 to 120:1 Q:M. As described, other ratios will be clear to those skilled in the art for any given scenario or based on the application rates described above and the concentrations of herbicides in suitable commercial formulations used to prepare the aqueous spray formulations used in the method of the invention.

[0036] In one embodiment, the quinclorac is in the acid form, hi another embodiment, the quinclorac is in the salt form.

[0037] According to the method of the present invention, an aqueous spray composition containing a herbicidally effective amount of quinclorac or its salt and an effective amount of metcamifen safener can suppress or regulate the growth of broadleaf weeds or grass weeds growing in the grass habitat in the presence of synthetic auxin (quinclorac) sensitive warm-season (C4) grass species (such as St. Augustine grass). The suppression or regulation effect includes any deviation from natural growth, such as death, growth retardation, leaf withering, chlorosis, dwarfing, and germination inhibition. For example, broadleaf weeds or grass weeds that do not die are often stunted and inhibited from flowering, making them non-competitive. The term "plant" refers to any physical part of a plant, such as seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

[0038] The aqueous spray composition used in the method of the present invention can be prepared by mixing a quinclorac-containing composition, a metcamifen-containing composition, and optionally a suitable surfactant or adjuvant (such as methylated seed oil) immediately before application by the end user to the foliage of unwanted broadleaf or grass weeds growing in the presence of synthetic auxin (quinclorac)-sensitive warm-season (C4) turfgrass species to be controlled or controlled in the field. Such compositions are commonly referred to as "tank-mix" compositions. Suitable tank-mix compositions can be prepared by mixing commercially available compositions of active ingredients. Examples of suitable commercially available quinclorac formulations include DRIVE XLR8 Herbicide (BASF Corporation) and Quali-Pro Quinclorac 75DF (Control Solutions, Inc.).

[0039] Alternatively, the compositions used in the methods of the present invention can be provided to the end user already formulated to the desired dilution for application ("ready to use" compositions), or can be supplied in a pre-built concentrate form that requires dilution, dispersion or dissolution with water by the end user ("concentrate" compositions). Ready to use forms are particularly suited to the consumer market. Concentrate formulations can be used in consumer and professional markets alike. Such pre-formulated concentrates can be liquids or particulate solids.

[0040] The aqueous spray compositions useful in the present invention are generally formulated in various ways using formulation aids such as carriers, solvents and surfactants.The concentrate compositions can be in various physical forms, such as dusts, gels, wettable powders (dusts), wettable powder granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, microemulsifiable concentrates, aqueous emulsions, oil-flowables, aqueous suspensions, oil suspensions, suspoemulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (containing water or water-miscible organic solvents as carriers), impregnated polymer films or other forms known, for example, from Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010).As indicated above, such compositions can be used directly or diluted before use by tank mixing.Dilution can be carried out, for example, with water, liquid fertilizers, micronutrients, biological organisms, oils or solvents.

[0041] Aqueous spray compositions can be prepared by mixing quinclorac and metcamifene (the "active ingredient") together with formulation auxiliaries to obtain a composition in the form of a finely divided solid, granules, solution, dispersion, emulsion, microemulsion or suspoemulsion. The active ingredient can also be formulated with other auxiliaries 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.

[0042] The active ingredient can also be contained in fine microcapsules. Microcapsules contain the active ingredient in a porous carrier. This allows the active ingredient to be released into the environment in controlled amounts (e.g., sustained release). Microcapsules usually have a diameter of 0.1 to 500 microns. The microcapsules contain the active ingredient in an amount of about 25 to 95% by weight of the capsule weight. The active ingredient can be in the form of a monolithic solid, in the form of fine particles in a solid or liquid dispersion, or in the form of a suitable solution. The encapsulating membrane can include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane or chemically modified polymers and starch xanthate or other polymers known to those skilled in the art. Alternatively, fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of the substrate, but the microcapsules themselves are not encapsulated.

[0043] Formulation auxiliaries suitable for the preparation of the aqueous spray composition used in the method of the present 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 abietate, 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, alkyl pyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-Heptanone, alpha-pinene, d-limonene, ethyl lactate, 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, 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 higher alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc. may be used.

[0044] 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.

[0045] Many surface-active substances can be used advantageously in both solid and liquid formulations, especially in formulations which may 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; salts of alkylaryl sulfonic acids, 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; salts of alkylnaphthalene sulfonic acids, 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, such as those described in, for example, McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New York, 1989. Also included are further substances described in Jersey (1981).

[0046] Further auxiliaries which 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, absorption enhancers, micronutrients, plasticizers, flow regulators, lubricants, dispersants, thickeners, antifreeze agents, fungicides and liquid and solid fertilizers.

[0047] The composition 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 oils and oil derivatives. 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 in the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oil or oil of vegetable origin (e.g. rapeseed oil, olive oil or sunflower oil), emulsified vegetable oil, alkyl ester of oil of vegetable origin (e.g. methyl derivatives) or oil of animal origin (e.g. fish oil or beef tallow, etc.). Preferred oil additives are C 8 ~C 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). Compendium of Herbicide Adjuvants, 10 th A large number of oil derivatives are known from the Journal of Chemical Industry, Vol. 13, No. 1, 2010, Issue 1, Springer-Verlag, 2010.

[0048] Compositions useful in the method of the invention generally contain 0.1 to 99% by weight, especially 0.1 to 95% by weight, of active ingredient and 1 to 99.9% by weight of formulation adjuvants, preferably including 0 to 25% by weight of surfactant. Commercial products used in tank mixes are preferably formulated as concentrates, but aqueous spray compositions applied by end users will usually use dilute formulations.

[0049] The aqueous spray composition used in the method is applied as a post-emergence application of an aqueous spray solution, which is accomplished by conventional methods (flooding, spraying, misting), such as post-emergence application of an aqueous foliar spray solution. The term "post-emergence" in the context of the present invention shall mean that the spray composition is applied after the targeted broadleaf or grass weeds, including synthetic auxin (quinclorac) sensitive warm-season (C4) turfgrass species, emerge from the turfgrass habitat. Post-emergence targeted broadleaf or grass weeds shall include growing and established plants. The quinclorac and metcamifen compounds may be applied simultaneously or sequentially (in any order) to the turfgrass habitat. In this example, the components are usually applied within 3 days of each other, most preferably within 24 hours. Suitably, all components are applied within a period of a few hours, for example, 1 hour. Alternatively, preferably the individual components are applied simultaneously to the turfgrass habitat as a single aqueous spray herbicidal composition by aqueous spray application. When the components are applied simultaneously, they can be applied separately, or as a tank mix, or as a preformulated mixture of all the components, or as a preformulated mixture of some of the components that are subsequently tank mixed with the remaining components.

[0050] In a preferred embodiment, a method for controlling unwanted broadleaf or grass weeds in a turfgrass habitat comprises applying a broadleaf or grass weed controlling amount of an aqueous spray composition to the foliage of unwanted broadleaf or grass weeds after emergence, growing, or established in the turfgrass habitat in the presence of a synthetic auxin (quinclorac) sensitive warm season (C4) turfgrass species, preferably St. Augustine grass. The method of the present invention is also useful for spot treating broadleaf or grass weeds growing in the turfgrass habitat or clearing any broadleaf or grass weeds from the turfgrass habitat.

[0051] In one embodiment for a particular turfgrass habitat, the method of the present invention can be practiced with a 7-42 day application schedule, preferably with an application regimen including 1-3 subsequent successive application at intervals of 14-21 days.

[0052] Optionally, the invention includes the use of mixtures of two or more herbicides, for example to extend the spectrum of weed control. Mesotrione, sulcotrione, benzobicyclon, tembotrione, and topramezone (HPPD herbicides, triketones). Others include isoxazole herbicides (isoxaflutole and isoxachlorthor), and pyrazole herbicides (benxofenap, pyrazolinate, and pyrazoxyfen), dithiopyr and thiazopyr (pyridine herbicides), trifloxysulfuron (sulfonylurea herbicide). Trifloxysulfuron is only one of many herbicides that act as a sulfonylurea herbicide. Other sulfonylurea herbicides include metsulfuron, chlorsulfuron, halosulfuron, foramsulfuron, rimsulfuron, sulfosulfuron, flazasulfuron, and iodosulfuron. Examples of imidazolinone herbicides include imaziquine, imazapyr, and imazapic. Examples of triazolopyrimide herbicides include cloransulam-methyl, florasulam, flumetsulam, and penoxsulam. Examples of pyrimidinyl benzoate herbicides include bispyribac-Na. Examples of sulfonylaminocarbonyl-triazolinone herbicides include flucarbazone-Na and theincarbazone-methyl. Atrazine and simazine (triazine herbicides). Amicarbazone (triazinone herbicides). Siduron (urea herbicide) carfentrazone-ethyl and sulfentrazone (triazolinone herbicides). Butafenacil (pyrimidinedione herbicide). Bentazon (benzothiadiazinone herbicide). Isoxaben (benzamide herbicide). Indaziflam (an alkylazine herbicide). Ipfencarbazone (a tetrazolinone herbicide). Quinclorac (a quinoline carboxylic acid herbicide). Ethofumesate (a benzofuran herbicide). 2,4-D, 2,4-DB, MCPP (phenoxy-carboxylic acid herbicides). Dicamba (a benzoic acid herbicide). Clopyralid, triclopyr, and fluroxypyr (pyridine carboxylic acid herbicides). Oxadiazon (an oxadiazole herbicide).Prodiamine (a dinitroaniline herbicide), other DNAs include pendimethalin, trioryzalin, and trifluralin. Fluazifop-p-butyl (aryloxyphenoxy-propionate "FOPS" herbicides - fluazifop-p-butyl, clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, haloxyfop-R-methyl, propaquizafop, metamifop, and quizalofop-P-ethyl. Examples of cyclohexanedione "DIMS" herbicides include alloxydim, butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim. Glyphosate (glycine herbicide) - for conventional and genetically modified turfgrass. Glufosinate-ammonium (phosphine herbicide) - for conventional and genetically modified turfgrass. S-metolachlor and dimethenamid-P (chloroacetamide herbicides).

[0053] Also, for example, a mixture of two or more safeners, such as cloquintocet, cyprosulfamide, and isoxadifen-ethyl, can be used in combination with metcamifen to increase selectivity (i.e., to reduce damage to a wider range of desirable turfgrass species by the herbicide composition).

[0054] In some cases, herbicidal active ingredients have been shown to be more effective when combined with plant growth regulators (PGRs) than when applied alone. The following PGR compounds and PGR drug groups have been of interest: Plant growth regulators include azole PGRs (such as uniconazole and paclobutrazol), cyclohexane carboxylates (such as trinexapac-ethyl and prohexadione-calcium), pyrimidinyl carbinols (such as fluprimidol and ancymidol), quaternary ammoniums (such as chlormequat-chloride and mepiquat-chloride), sulfonyl-aminophenyl-acetamides (such as mefluidide), cycloalkenes (such as 1-methylcyclopropene), and hydrochlorides (such as aminoethoxyvinylglycine). Plant growth regulators such as trinexapac-ethyl are commonly used on turfgrass to improve turfgrass color and quality, reduce mowing frequency, and improve establishment.

[0055] The methods of the present invention can be used against many unwanted grass and broadleaf weeds. Examples of unwanted grass and broadleaf weeds that may be managed or controlled by the method of the present invention include grass weeds such as Echinochloa crusgalli, Digitaria sanguinalis, Digitaria ischaemum, Setari faberi, Setari viridis, Setari glauca, Pennisetum clandestinum, Brachiaria platyphylla, and Panicum repens; convolvulus arvensis, Trifolium aureum Pollich, Trifolium pretense, Trifolium repens, Bellis persica, and other grass weeds. Broadleaf weeds such as Taraxacum perenne, Taraxacum officinale, Hydrocotyle umbellate, Geranium carolinium, Medicago lupuline, Ipomea sp., Veronica officinalis, Veronica filiformis, Veronica serpyllifolia, and Viola sp. are particularly undesirable weeds such as bighorn and crabgrass.

[0056] In one embodiment, the sensitive warm-season (C4) turfgrass species include, but are not limited to, Cynodon L.C. Rich, Zoysia Willd., Stenotaphrum secundatum (Walt.) Kuntze, Eremochloa ophiuroides (Munro.) Hack., Buchloe dactyloides (Nutt.) Engelm., and Paspalum vaginatum. In one embodiment, the sensitive warm-season (C4) turfgrass species is synthetic auxin (quinclorac) sensitive. Preference is given to St. Augustine grass.

[0057] Various aspects and embodiments of the invention will now be described in more detail by way of example. It will be appreciated that modifications of detail may be made without departing from the scope of the invention. EXAMPLES

[0058] Example 1 In a study conducted on St. Augustinegrass (Floratam), two formulations of quinclorac (Quinclorac 75 DF and Drive XLR8) were applied at 573 g ai / ha with or without metcamifen at 75 g ai / ha. Two applications were made 21 days apart. Quinclorac alone caused severe damage with both formulations. Five weeks after the first application, Drive XLR8 and Quinclorac 75 DF caused 73.8% and 28.8% damage, respectively. The addition of metcamifen to each of these products reduced damage to 12.5% ​​and 2.5%, respectively.

[0059] [Table 1]

[0060] Example 2 In a second trial on 'Floratam' St. Augustinegrass, two formulations of quinclorac were applied again at 573 g ai / ha with or without metcamifen at 75 g ai / ha. Adding metcamifen 6 weeks after the first application reduced injury caused by Quinclorac 75 DF from 66.3% to 12.5%.

[0061] [Table 2]

[0062] Example 3 Quinclorac was applied at 573 g ai / ha with or without metcamifene at 75 g ai / ha. Two applications were made 21 days apart. Quinclorac controlled bigleaf caneweed and, more importantly, efficacy was not reduced by the addition of metcamifene.

[0063] [Table 3]

[0064] Example 4 In a study conducted on St. Augustinegrass (Floratam), quinclorac was applied at 573 g ai / ha with or without metcamifene at 75 g ai / ha. Two applications were made 21 days apart. Quinclorac provided excellent and significant control of blanket crabgrass. Quinclorac applied at 573 g ai / ha with or without metcamifene provided greater than 90% control of blanket crabgrass.

[0065] [Table 4]

[0066] These data demonstrate the effectiveness and novelty of using metcamiphen to reduce herbicide toxicity in St. Augustinegrass without losing weed control (weed inhibition).

Claims

1. A method for selectively controlling weeds in a turfgrass, comprising applying a herbicidal amount of quinchlorac or a salt thereof and a phytotoxicity-reducing amount of metcamifen to a synthetic auxin-sensitive turfgrass.

2. The method according to claim 1, comprising selectively controlling unwanted weeds in a turfgrass habitat in the presence of susceptible warm-season (C4) turfgrass, wherein the control comprises applying an effective amount of quinchlorac or a salt thereof and a phytotoxicity-reducing amount of metcamifen to the turfgrass habitat.

3. The method according to claim 1, comprising selectively controlling unwanted weeds in a turfgrass habitat in the presence of St. Augustine grass without inhibiting the herbicidal effect, wherein the control comprises applying a composition containing an effective herbicidal amount of quinchlorac or a salt thereof and a phytotoxicity-reducing amount of metcamifen to the turfgrass habitat.

4. The method according to any one of claims 1 to 3, wherein quinchlorac is applied in an acidic form.

5. The method according to any one of claims 1 to 3, wherein quinchlorac is applied or incorporated as a salt such as a dimethylamine salt.

6. The method according to any one of claims 1 to 3, wherein Kinklorac is applied to the habitat of the turfgrass at a rate of 140 to 2240 g ai / ha or 140 to 2240 g ae / ha.

7. The method according to any one of claims 1 to 3, wherein metcamifen is applied to the habitat of the turfgrass as (2-methoxy-N-[[4-[[(methylamino)carbonyl]amino]phenyl]sulfonyl]benzamide).

8. The method according to any one of claims 1 to 3, wherein metcamifen is administered or incorporated as a crystalline polymorph called Form 1.

9. The method according to any one of claims 1 to 3, wherein metcamifen is administered or incorporated as a crystalline polymorph called form 2.

10. The method according to any one of claims 1 to 3, wherein metcamifen is administered or incorporated as a crystalline polymorph called form 3.

11. The method according to any one of claims 1 to 3, wherein metcamifen is applied to the habitat of the turfgrass at a rate of 5 to 300 g ai / ha.

12. The method according to any one of claims 1 to 3, wherein quinchlorac and metcamifen are applied to the habitat of the turfgrass by foliar treatment after germination.

13. The method according to any one of claims 1 to 3, wherein quinchlorac and metcamifen are applied to the habitat of the turfgrass in an aqueous spray composition.

14. The method according to claim 13, wherein the amount of aqueous spray solution applied to the habitat of the turfgrass is 100 to 300 l / ha.

15. The method according to any one of claims 1 to 2, wherein the susceptible turfgrass is a warm-season (C4) turfgrass species selected from Bermuda grass (Cynodon L.C. Rich), Zoysia grass (Zoysia Willd.), St. Augustine grass (Stenotaphrum secundatum (Walt.) Kuntze), centipede grass (Eremochloa ophiuroides (Munro.) Hack.), buffalo grass (Buchloe dactyloides (Nutt.) Engelm.), and barnyard grass (Paspalum virginatum).

16. The method according to claim 15, wherein the susceptible turfgrass is St. Augustine grass.

17. The aforementioned unwanted weeds include grasses such as barnyard grass (Echinochloa crusgalli), crabgrass (Digitaria sanguinalis), northern crabgrass (Digitaria ischaemum), blanket clubgrass (Digitaria serotina), autumn foxtail grass (Setari faberi), foxtail grass (Setari viridis), golden foxtail grass (Setari glaucoma), chrysanthemum grass (Pennisetum clarestinum), corn millet (Brachiaria platyphylla), and large brown millet (Panicum repens); and convolvulus. arvensis), Trifolium aureum Pollich, Trifolium presente, Trifolium repens, Bellis perenne, Taraxacum officinale, Hydrocotyle umbellate, Geranium carolinium, Medicago lupuline, Ipomoea sp., Veronica officinalis, Veronica The method according to any one of claims 1 to 3, selected from broadleaf weeds such as *Dorcus filiformis*, *Veronica serpyllifolia*, and wild violet (Viola sp.).

18. The method according to claim 17, wherein the undesirable weed is selected from sorghum and crabgrass.

19. A herbicide composition for use on turfgrass susceptible to damage from synthetic auxin herbicides, comprising a) an effective amount of quinchlorac or a salt thereof for herbicidal purposes, and b) an effective amount of metcamifen for reducing phytotoxicity, wherein the quinchlorac or salt thereof can be safely used on the turfgrass.

20. A method for reducing plant toxicity to warm-season (C4) turfgrass such as St. Augustine grass by applying a synthetic auxin-based herbicide compound such as quinchlorac or a salt thereof, either alone or as a mixture with one or more herbicide combination compounds, the method comprising applying an effective amount of metcamifene to the habitat of the turfgrass.