[0001] The present invention relates to a method of controlling the growth of weeds turfgrass using a herbicidal composition comprising certain herbicidal dihydro-hydantoins. More particularly, the invention is concerned with the selective control, reduction, or elimination of undesirable vegetation components of turf, especially of high quality sport or amenity turf containing cool and warm season turf grasses.

[0002] The protection of crops from weeds and other vegetation that inhibit crop growth is a constantly recurring problem in agriculture. In addition, aesthetically, it may be of interest to remove such unwanted weeds and vegetation, for example, when growing turf in areas such as golf courses, sports fields, residential lawns and public parks. Weed control is one of the most challenging problems that turfgrass managers face in maintaining turfgrass at a standard of quality expected by users; it is sometimes difficult to selectively control the weeds without causing unacceptable injury to the turfgrasses.

[0003] One specific example of a common weed problem for golf course managers is Poa annua (also called Annual Bluegrass). P. annua can be particularly troublesome in bent grass putting greens as it is susceptible to abiotic stress, particularly water availability, as well as succumbing to a number of fungal diseases. In addition, if a green is composed of patches of P. annua and bent grass, or P annua and bermudagrass, the surface is not as uniform and reduces playability. Phytotoxic damage from removal efforts can create additional playability and aesthetic value losses. [0004] To help combat these problems, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use. Some synthetic herbicides are analogs of natural products. Other herbicides and control techniques based on natural products are also known. However, many of the herbicides are for broad- leaf weeds but not grassy weeds.

[0005] In addition, an important factor in influencing the usefulness of a given herbicide is its selectivity towards the non-target turfgrasses. In some cases, a beneficial turfgrass is susceptible to the effects of the herbicide. Suitable herbicides must cause only commercially acceptable damage (suitably minimal or no damage) to the beneficial turfgrass while maximizing damage to the target undesired turf grass or weed (in this case, Poa annua) which infest the locus of the high quality golf, sport or amenity turfgrass.

[0006] While there are numerous herbicides and control techniques currently available that have been tested against grassy weeds such as P. annua with varying levels of success, few agents are currently available for selective control of P. annua in turfgrass without causing unacceptable injury to the non-target turfgrasses. Suitable herbicide applications are controlled by course budget, availability of appropriate equipment, availability of qualified personnel. In addition, certain herbicides are subject to regulatory and product label use restrictions and/or may only be selectively used for resistance management reasons.

[0007] The compound 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazol idin-2- one is a dihydro-hydantoin having known herbicidal activity as shown, for example, in WO 2015/059262.

[0008] High quality, healthy turf is essential, for example, to the golfing industry and weed control is an essential component of managing such turf health and quality. Poa annua is considered a weed in most instances due to the current lack of commercially available herbicides to safely control this grass within cool-season turf plantings. Accordingly, there is a continued need for alternative methods to control P. annua in such turfgrass without undue phytotoxic effects. Accordingly, the present invention provides a method for selectively controlling or modifying the growth of annual bluegrass (Poa annua) in turf grass without causing significant injury to the turf grass, comprising applying to the turf grass or to locus of the Poa annua in such turf grass, a herbicidally effective amount of a composition comprising a compound represented by the structural formula (I):

[0009] In one embodiment, the method of invention relates to the use of a herbicidally effective amount of the compound of formula (I) (i.e., 4-hydroxy-l-methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one) for selectively controlling or modifying the growth of Poa annua in turf grass selected from creeping bentgrass (Agrostis stolonifera) and dormant bermudagrass (Cynodon dactylon) without causing significant injury to the turf grass, for example, relative to an untreated control.

[0010] In another embodiment, the method of invention relates to the use of a herbicidally effective amount of the compound 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2- pyridyl]imidazolidin-2-one as represented by the formula (I) for selectively controlling or modifying the growth of Poa annua in turf grass selected from creeping bentgrass (Agrostis stolonifera) without causing significant injury to the turf grass, for example, relative to an untreated control.

[0011] In a further embodiment, the method of invention relates to the use of a herbicidally effective amount of the compound 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2- pyridyl]imidazolidin-2-one as represented by the formula (I) for selectively controlling or modifying the growth of Poa annua in turf grass selected from dormant bermudagrass (Cynodon dactylon) without causing significant injury to the turf grass, for example, relative to an untreated control.

[0012] In particular, the present invention relates to a method for selectively controlling or modifying the growth of Poa annua in a turf grass selected from creeping bentgrass (Agrostis stolonifera) and dormant bermudagrass (Cynodon dactylon) without causing significant injury to the turf grass, comprising applying to the turf grass or to the locus of the Poa annua in such turf grass, a herbicidally effective amount of a composition comprising a compound represented by the structural formula (I).

[0013] The term 'herbicide' as used herein denotes a compound which controls or modifies the growth of undesired plants, in particular Poa annua. In the context of the present invention, the term 'herbicidally effective amount' indicates the quantity of the compound of formula (I) alone as active ingredient (a.i.) (or in combination with other active compounds, active ingredients) which is capable of producing a controlling or modifying effect on the growth of Poa annua. Controlling or modifying effects include all deviation from natural development, for example: killing, retardation, leaf burn, albinism, dwarfing and the like. For example, Poa annua plants that are not killed are often stunted and non-competitive with flowering disrupted (poa seed head reduction). The term 'plants' refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage and fruits. [0014] The herbicidally effective amount or rate at which a compound of formula (I) is applied in accordance with the method of the invention will depend upon the particular type and nature of turfgrass in which the Poa annua is to be controlled, the amount of Poa annua present in the turfgrass, the degree of control required and the timing and method of application. For example, herbicidally effective rates may vary for when controlling Poa annua on golf course turf or general amenity turf. Also, it will be understood that rate variations may be required within particular golf course turfs such as fairway-height turfs and golf greens and tees.

[0015] In one embodiment, the compound of formula (I), can be applied at an application rate of betweenl to 400g a.i./ha (gram active ingredient per hectare), based on the total amount of active ingredient in the composition used for carrying out the method of suppressing or controlling Poa annua. An application rate of between about 1 and about lOOg a.i/ha is particularly suitable, more particularly, a rate of between about 5 to 50g a.i./ha with an application rate of between about 5 and 25 being especially suitable. In one embodiment, a rate of between 12.5 and 25g a.i./ha is preferred.

In another embodiment, the compound of formula (I), can be applied at an application rate of between 25 to 400g a.i./ha on an annual loading basis (the cumulative rate per turf growing season) is provided, based on the total amount of active ingredient in the composition used for carrying out the method of suppressing or controlling Poa annua. In one embodiment, an application rate on an annual loading basis of between about 50 and about 300g a.i./ha is suitable. In another embodiment, a rate of an application rate on an annual loading basis of between about 50 and about 200g a.i./ha is preferred.

[0016] In another embodiment, a compound of formula (I) can be applied or re-applied to the turf grass or to the locus thereof for carrying out the method of suppressing or controlling Poa annua at intervals of from 5 to 42 days, up to the cumulative rate per turf growing season of between 25 and about 400, based on the total amount of active ingredient in the composition. Rates and number of application for cool and warm season turf and greens, tees, fairways and roughs within these parameters may vary based on local conditions.

[0017] In a more specific embodiment, in the practice of the methods of the invention, a composition comprising a compound of formula (I), can be applied or re-applied to the turfgrass or to the locus thereof for carrying out the method of suppressing or controlling Poa annua at intervals of from 7 to 21 days; more specifically, from 7 to 14 days, up to the cumulative rate of the compound of formula (I) a.i. for the turfgrass locus being treated. For example, in one embodiment, the control of Poa annua and safety to creeping bentgrass (Agrostis stolonifera) and dormant bermudagrass (Cynodon dactylon) is improved when 4- hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolid in-2-one is applied sequentially at 14 day intervals to deliver the total active ingredient quantity of between 25 and 300 over a 90 day period. In another embodiment, the cumulative annual rate is achieved by 4 applications in the fall and 4 applications in the spring. [0018] The weed species to be controlled by the inventive method is Poa annua or Annual bluegrass (also called annual meadow grass). In one embodiment, The method of the invention is also suitable for selective control of (Poa annua var. annua L.) or (Poa annua var. Reptans). The 'locus' is intended to include an established growing beneficial turf grass which contains or may contain seeds, seedlings and/or established vegetation of Poa annua

[0019] The 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazol idin-2-one compositions useful in the practice of the invention have been found to be highly effective for use in controlling the growth of Poa annua in cool and warm season turf grasses selected from creeping bentgrass (Agrostis stolonifera) and dormant bermudagrass (Cynodon dactylon) without causing significant injury to such turf grass when applied in accordance with the inventive method. More specifically, the safety benefits of the present invention are observed when a composition containing a compound of formula (I) is applied or reapplied to control Poa annua in growing creeping bentgrass (Agrostis stolonifera) wherein the levels of phytotoxicity observed for Poa annua are significantly higher than the phytotoxicity for the creeping bentgrass (Agrostis stolonifera) in which the Poa annua is growing or present as seed, seedlings or established vegetation. This allows for a selective control of the Poa annua within an established growing beneficial creeping bentgrass (Agrostis stolonifera) turf grass; in particular, a golf turf grass selected from fairway, green or tee turf grass.

[0020] In one embodiment, practice of the invention to control Poa annua without causing significant injury to the creeping bentgrass (Agrostis stolonifera) or and dormant bermudagrass (Cynodon dactylon) means that the application of 4-hydroxy-l-methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one, does not result in serious injury to the treated cool and warm -season turf grass in a manner which would render the method commercially and functionally unacceptable; including an injury to the turf from which the turf does not recover in an acceptable period of time.

[0021] In the context of the present method, the term dormant bermudagrass (Cynodon dactylon) is elaborated as follows, wherein: application of the 4-hydroxy-l-methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one a.i. of formula (I) can cause significant injury when applied in the greenhouse or to actively growing bermudagrass (Cynodon dactylon). Poa annua is a problem in bermudagrass in temperate climate zones. Poa annua grows as a winter annual, germinating in the fall and dying the following spring as temperatures increase. In temperate climate zones bermudagrass, a warm season grass, goes dormant and stops growing from the fall until the following spring. During this dormancy period (e.g., dormant bermudagrass (Cynodon dactylon)), the method of the invention provides that 4- hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolid in-2-one can be safely applied to such dormant bermudagrass and provide acceptable weed control of Poa annua. In one embodiment, the method for selectively controlling or modifying the growth of actively growing Poa annua in dormant bermudagrass (Cynodon dactylon) without causing significant injury to such turf grass. The rate and interval embodiments for the method mentioned above are also valid for the control of actively growing Poa annua in dormant bermudagrass.

[0022] In another embodiment, the method of invention to control Poa annua without causing significant injury to the turf grass selected from creeping bentgrass (Agrostis stolonifera) and dormant bermudagrass (Cynodon dactylon) means the application of a compound of formula (I) in a manner according to the method mentioned above that results in less than 66% phytotoxicity to the desired cool and warm-season turf grass relative to an untreated control, more particularly, less than 50% phytotoxicity, even more particularly, less than 33% phytotoxicity to the desired turf grass relative to an untreated control, more particularly, less than 25% phytotoxicity to the desired turf grass relative to an untreated control, even more particularly, less than 10% phytotoxicity to the desired turf grass relative to an untreated control, and even more particularly, less than 5% phytotoxicity to the desired turf grass relative to an untreated control; in each case, wherein the levels of phytotoxicity observed for Poa annua are significantly higher than the phytotoxicity for the desired turf grass in which the Poa annua is growing or present as seed, seedlings or established vegetation.

[0023] In one embodiment, the above mentioned phytotoxicity measurement of the creeping bentgrass (Agrostis stolonifera) or bermudagrass (Cynodon dactylon) treated in accordance with the above described method relates to a phytotoxicity evaluation made 7 days after application of the compound of formula (I), more particularly, 14 days after application of the compound of formula (I). In another embodiment, the above described method relates to a phytotoxicity evaluation made 21 days after application of the compound of formula (I) and, more particularly, 90 days after initial application. In a further embodiment, a phytotoxicity evaluation is made 120 days after application of the compound of formula (I)..

[0024] In accordance with the method herein, suitable cool-season and warm season turf grass is understood to include creeping bentgrass (Agrostis stolonifera) or bermudagrass (Cynodon dactylon)..

[0025] In addition, the creeping bentgrass (Agrostis stolonifera) or bermudagrass (Cynodon dactylon) within the context of the present invention is to be understood to include those turfgrasses that have been made tolerant to abiotic or biotic pests and pesticides, including herbicides or classes of herbicides (and, suitably, the herbicides of the present invention), as a result of conventional methods of breeding (native traits) or by genetic engineering.

Tolerance to herbicides means a reduced susceptibility to damage caused by a particular herbicide compared to conventional turfgrass breeds. Turfgrass can be modified or bred so as to be tolerant, for example, to HPPD inhibitors such as mesotrione, EPSPS inhibitors such as glyphosate or to glufosinate. Tolerance to abiotic stress means, for example, drought tolerance or heat tolerance. Tolerance to biotic pests means, for example, insect, nematode, or disease resistance. In accordance with the method of the present invention, the application of compositions which contain 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazol idin-2-one to a locus comprising an established stand of a beneficial creeping bentgrass (Agrostis stolonifera) or dormant bermudagrass (Cynodon dactylon) is suitable for pre-emergence control of Poa annua or post-emergence control of Poa annua in such locus and acceptable selectivity to the desired beneficial turfgrass. In one embodiment, therefore, the method of the invention is practiced as a pre-emergent Poa annua control application. In a further embodiment, the method of the invention is practiced as a post-emergent Poa annua control application. In one embodiment, the rate and interval embodiments for the method as mentioned above are also valid for the pre-emergence control of Poa annua. In another embodiment, the rate and interval embodiments for the method as mentioned above are also valid for the control of post-emergent or actively growing Poa annua.

[0026] In addition, further, other biocidally active ingredients or compositions may be combined with 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazol idin-2-one, in the practice of the method according to the invention. For example, the compositions useful in the method of the invention may contain, in addition to compound of formula (I), other herbicides, herbicide safeners insecticides, fungicides, bactericides, acaracides, nematicides, wetting agents and/or plant growth regulators, Fe chelates, Cu chelates in order to broaden the spectrum of activity as a turf management tool. For instance, it may be advantageous to use other active ingredients that are commonly used in standard turf management practices or to combine other bioactive components with compound of formula (I) as follows:

[0027] Herbicides such as:

Methiozolin (oxazole herbicide chemistry); Cinmethylin (unclassified herbicide chemistry)

Mesotrione, bicyclopyrone, sulcotrione, benzobicyclon, tembotrione and topramezone ( HPPD herbicide chemistry, Triketone). Others include isoxazoles herbicide chemistry - isoxaflutole and isoxachlortole, and pyrazole herbicide chemistry - benxofenap, pyrazolynate and pyrazoxyfen;

Prodiamine and pendimethalin (DNA herbicide chemistry); Dithiopyr and thiazopyr (Pyridine herbicide herbicide);

Trifloxysulfuron, metsulfuron, chlorsulfuron, halosulfuron, foramsulfuron, rimsulfuron, sulfosulfuron, flazasulfuron, iodosulfuron, and orthosulfamuron (Sulfonylureas herbicide chemistries).

Examples of imidazolinone herbicide chemistry include imazapyr.imaziquin, imazapyr and imazapic;

Examples of triazolopyrimide herbicide chemistry include cloransulam-methyl, florasulam, flumetsulam, penoxsulam;

Eamples of pyrimidinyl benzoate herbicide chemistry include bispyribac-sodium and pyrithiobac-sodium;

Examples of sulfonylamino-carbonyl-triazolinone herbicide chemistry include flucarbazone-sodium, and theincarbazone-methyl;

Atrazine and Simazine (Triazine herbicide chemistry);

Amicarbazone (Triazinone herbicide chemistry);

Siduron (Urea herbicide chemistry);

Carfentrazone-ethyl and sulfentrazone (Triazolinone herbicide chemistry); Butafenacil (Pyrimidindione herbicide chemistry);

Bentazon (Benzothiadiazinone herbicide chemistry);

Isoxaben (Benzamide herbicide chemistry);

Indaziflam (Alkylazine herbicide chemistry);

Ipfencarbazone (Tetrazolinones herbicide chemistry);

Quinclorac (Quinoline carboxylic acid herbicide chemistry);

Ethofumesate (Benzofuran herbicde chemistry);

2,4-D, 2,4-DB, MCPP ( Phenoxy-carboxylic acid herbicide chemistry);

Dicamba (Benzoic Acid herbicide chemistry);

Clopyralid, fluroxpyr , halauxifen, triclopyr and (Pyridine carboxylic herbicide chemistry).

Oxadiazon (Oxadiazole herbicide chemistry);

Prodiamine, pendimethalin, trioryzaline and trifluralin (Dinitroaniline herbicide chemistry);

Fluazifop-p-butyl, clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P-ethyl, haloxyfop-R-methyl, propaquizafop, metamifop and quizalofop- P-ethyl (Aryloxyphenoxy-propionate "FOPS" herbicide chemistry). Alloxydim, butroxydim, clethodim, cycloxydim, profoxydim, sethoxydim, tepraloxydin, tralkoxydim (Cyclohexanedione "DIMS" herbicide chemistry). Pinoxaden

(Phenylpyrazoline "DEN" herbicide chemistry). Glyphosate (Glycine herbicide chemistry) - Native and transgenic turf;

Glufosinate-ammonium (Phosphinic herbicide chemistry) - Native and transgenic turf;

S-metolachlor and dimethenamid-P (Chloroacetamide herbicide chemistry). Fungicides such as:

Triazoles includings propiconazole, difenoconazole, cyproconazole, triticonazole, metconazole, triadimefon and tebuconazole;

Strobilurins - azoxystrobin, trifloxystrobin, fluoxastrobin, picoxystrobin and pyraclostrobin ; Fludioxonil;

Thiabendazole;

SDHIs including - boscalid, fluopyram, fluxapyroxad, isopyrazam, penthiopyrad, Solatenol™; Adepidyn,

Chloronitriles - chlorothalonil;

Fluazinam;

Phenylamide - metalaxyl and mefonoxam; Phosphites; Dicarboxamides; and

Benzimidazole. [0029] Phytohormones and elicitors such as: abscisic acid, auxins, brassinolides, cytokinins, gibberillins, and strigilactones, acibenzolar-S-methyl, harpin, jasmonic acid, and salicylic acid. [0030] Insecticides and nematicides such as: thiamethoxam, imidacloprid, abamectin, milbamectin, permethrin, lambda cyhalothrin, cypermethrin, bifenthrin , fipronil, chlorotraniliprole, cyantraniliprole and fluopyram.

[0031] Soil Wetting Agents such as: alkyl polyglycosides (APG) and ethylene oxide- propylene oxide (EO/PO) block copolymer surfactants.

[0032] Plant Growth Regulators (PGRs): uniconazole and paclobutrazol (azole PGR

Chemistry, trinexapac-ethyl, and prohexadione-calcium (cyclohexane carboxylates), flurprimidol, and ancymidol (pyrimidinyl carbinols), chlormequat-chloride and mepiquat- chloride (quarternary ammoniums), and mefluidide (sulphonyl-amino phenyl-acetamides), 1- methylcyclopropene (cycloalkenes), and aminoethoxyvinylglycine (hydrochloride salts).

[0033] In a preferred embodiment, the method of invention comprises the use of a herbicidally effective amount of the compound 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)- 2-pyridyl]imidazolidin-2-one as represented by the formula (I), and a plant growth regulator (PGR) selected from trinexapac-ethyl and paclobutrazol for selectively controlling or modifying the growth of Poa annua in a turf grass selected from creeping bentgrass

(Agrostis stolonifera) and dormant bermudagrass (Cynodon dactylon) without causing significant injury to the turf grass.

[0034] In another embodiment, the method of invention comprises use of a PGR selected from paclobutazol. In one embodiment, suitable rates for palobutrazol are an annual application rate: from 1 to 2,241 g ai/ha/yr. In another embodiment, the per application rate of paclobutrazol within the method herein is: 30 to 840 gai/ha and more specifically 73 to 292g ai/ha.

[0035] In one embodiment, in the practice of the method of the invention, compound of formula (I), may be applied to creeping bentgrass (Agrostis stolonifera) or dormant bermudagrass (Cynodon dactylon) to control and/or manage Poa annua either simultaneously or sequentially with one or more of the foregoing herbicides, insecticides, fungicides, bactericides, acaracides, nematicides, wetting agents and/or plant growth regulators. For example, if administered sequentially, the components may be administered in any order in a suitable timescale, for example, with no longer than 24 hours between the time of administering the first component and the time of administering the last component.

Suitably, all the components are administered within a timescale of a few hours, such as one hour. In another embodiment, if the components are administered simultaneously, they may be administered separately or as a tank mix or as a pre-formulated mixture of all the components or as a pre-formulated mixture of some of the components tank mixed with the remaining components.

[0036] Herbicidal compositions used in the method of the invention can be prepared on site by the end-user shortly before application to the foliage of the vegetation of Poa annua to be killed or controlled by mixing in aqueous solution a composition containing compound of formula (I) and, optionally, additional active ingredients, suitable surfactants or adjuvants. Such compositions are typically referred to as "tank-mix" compositions.

[0037] Alternatively, the compositions used in the method of the invention may be provided to the end-user already formulated, either at the desired dilution for application ("ready to use" compositions) or requiring dilution, dispersion, or dissolution in water by the end-user ("concentrate" compositions). Such preformulated concentrates can be liquids or particulate solids. The compositions useful in the practice of the inventive method may thus be formulated as granules, as wettable powders, as emulsifiable concentrates, as powders or dusts, as flowables, as solutions, as suspensions or emulsions, or as controlled release forms such as microcapsules. These formulations may contain as little as about 0.5% to as much as about 95% or more by weight of active ingredient. The optimum amount for any given formulation containing a compound of formula (I) will depend on the presence of other compounds, formulation type, application equipment and nature of the turf substrate in which the formulation is to be applied (and the P. annua is to be controlled). A non- limiting list of suitable formulation types for use in the inventive methods are described below, where "active ingredient" or "active compound" means the compound of formula (I) alone or in combination with another bioactive material. [0038] Wettable powders are in the form of finely divided particles which disperse readily in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain about 5% to about 95% of the active ingredient plus a small amount of wetting, dispersing or emulsifying agent.

[0039] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid and may consist entirely of the active compound with a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from about 0.5% to about 95% of the concentrate. [0040] Granular formulations include both extrudates and relatively coarse particles and are usually applied without dilution to the area in which suppression of vegetation is desired. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corn cobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulphate and other organic or inorganic materials which absorb or which can be coated with the active compound. [0041] For example, in one embodiment, the compound of formula (I) is impregnated on controlled release fertilizer granules: Impregnation on granules: polymer-coated (Polyon™, Duration™, ESN™), polymer-coated sulfur coated (poly-S™), sulfur-coated (SCU), resin- coated (Osmocote™) or are impregnated on other granules such as palletized limestone, corncobs, clay, paper, and peanut hulls.

[0042] Granular formulations normally contain about 5% to about 25% active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins. The granular substrate material can be one of the typical carriers mentioned above and/or can be a fertiliser material e.g. urea/formaldehyde fertilisers, urea, potassium chloride, ammonium compounds, phosphorus compounds, sulphur, similar plant nutrients and micronutrients and mixtures or combinations thereof. [0043] Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.

[0044] Microcapsules are typically droplets or granules of the active material enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically about 1 to 50 microns in diameter. The enclosed liquid typically constitutes about 50 to 95% of the weight of the capsule and may include solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores. Granules typically range from 1 millimetre to 1 centimetre, preferably 1 to 2 millimetres in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell membrane materials include natural and synthetic rubbers, cellulosic materials, styrene- butadiene copolymers, poly aery lonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates. Suitable granules also include controlled-release granules which, for example, enable the release of sarmentine and/or its analogs uniformly over a 90 day period with a single application while improving Poa annua control efficacy and cool-season and warm season turfgrass safety.

[0045] Other useful formulations for use in the inventive methods include simple solutions of the active ingredients in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents. Pressurised sprayers, wherein the active ingredient is dispersed in finely-divided form as a result of vaporisation of a low boiling dispersant solvent carrier, may also be used.

[0046] Many of these formulations described above include wetting, dispersing or emulsifying agents. Examples are alkyl and alkylaryl sulphonates and sulphates and their salts, polyhydric alcohols; polyethoxylated alcohols, esters and fatty amines. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation.

[0047] Suitable agricultural adjuvants and carriers that are useful in formulating the compositions suitable for use in methods of the invention in the formulation types described above are well known to those skilled in the art. Suitable examples of the different classes are found in the non-limiting list below.

[0048] Liquid carriers that can be employed include water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, Ν,Ν-dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octyl amine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc. ethylene glycol, propylene glycol, glycerine, N-methyl-2- pyrrolidinone, and the like. Water is generally the carrier of choice for the dilution of concentrates.

[0049] Suitable solid carriers include talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin and the like.

[0050] A broad range of surface-active agents are advantageously employed in both said liquid and solid compositions, especially those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic, non-ionic or polymeric in character and can be employed as emulsifying agents, wetting agents, suspending agents or for other purposes. Typical surface active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonate salts, such as calcium

dodecylbenzenesulfonate; alky lphenol- alky lene oxide addition products, such as

nonylphenol-Ci8 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Ci6 ethoxylate; soaps, such as sodium stearate; alkylnaphthalenesulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium 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 dialkyl phosphate esters.

[0051] Other adjuvants commonly utilized in agricultural compositions include

crystallisation inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, synthetic pigments, biological pigments such as anthocyanin, antioxidants, foaming agents, light-blocking agents, compatibilizing agents, antifoam agents, sequestering agents, neutralising agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants, sticking agents, and the like. The compositions for use in the practice of the inventive methods can also be formulated with liquid fertilizers or solid, particulate fertiliser carriers such as ammonium nitrate, urea and the like.

[0052] To enhance the beneficial aspects of use of the compound of formula (I) in the control of Poa annua and to further minimize creeping bentgrass (Agrostis stolonifera) or dormant bermudagrass (Cynodon dactylon) turfgrass damage, it is suitable to apply the the compound of formula (I) in combination with an antidote or safener if necessary. As used here in 'antidote' or "safener" describes a compound which has the effect of establishing or enhancing herbicide selectivity, i.e. continued herbicidal phytotoxicity to weed species by the herbicide and reduced or non-phy to toxicity to the cultivated turf species. The term 'antidotally effective amount' describes an amount of an antidote compound which counteracts to some degree a phytotoxic response of a beneficial turf to an herbicide. If necessary or desired for a particular application or turf, the compositions containing the compound of formula (I) useful in the practice of the methods of the present invention may contain an antidotally effective amount of an antidote for the herbicides of the invention. Those skilled in the art will be familiar with antidotes which are suitable for use with optional herbicides that are useful in combining with the compound of formula (I) in the practice of the invention and can readily determine an antidotally effective amount for a particular compound and application. Among the suitable safeners there may be mentioned: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and

N-(2-Methoxybenzoyl) -4- [(methylaminocarbonyl)amino] benzenesulfonamide. It may also be mentioned that such antidotes or safeners can be in combination with turfgrass seed that is treated with such safener.

[0053] Each of the above formulations can be prepared as a package containing the compound of formula (I) together with other inert or active ingredients of the formulation (diluents, emulsifiers, surfactants, other a.i.s, etc.). As noted above, the formulations can also be prepared by a tank mix method, in which the ingredients are obtained separately and combined at the turfgrass application site.

[0054] These formulations can be applied to the areas where control is desired by conventional methods. Dust and liquid compositions, for example, can be applied by the use of power-dusters, broom and hand sprayers and spray dusters. The formulations for use in the inventive methods can also be applied from airplanes as a dust or a spray or by rope wick applications. To modify or control growth of germinating seeds or emerging seedlings, dust and liquid formulations can be distributed in the soil to a depth of at least one-half inch below the soil surface or applied to the soil surface only, by spraying or sprinkling. The formulations can also be applied by addition to irrigation water. This permits penetration of the formulations into the soil together with the irrigation water. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as discing, Dryject, Hydroject, dragging or mixing operations. [0055] The following examples are for illustrative purposes only. The examples are not intended as necessarily representative of the overall testing performed and are not intended to limit the invention in any way. It is noted that the rates used in the examples below are glasshouse rates and may be lower than those normally applied in the field as herbicide effects tend to be magnified in such conditions.

EXAMPLES

Materials and methods Example 1

[0056] Activity of the compound of formula (I) was evaluated in a randomized design experiment with 3 replicates in greenhouses (15/23°C night/day, relative humidity 50-60%).

[0057] Plastic pots (09 cm) or tubes (03.8 cm) were filled with native soil from 'Les Barges, Switzerland' (7.1 % clay; 25.4 % silt; 67.6 % sand; 2.4 % OM; pH (H ₂ 0) 7.5) and turf (Agrostis stolonifera AGSST, Poa annua POAAN). For all experiments, treatments were applied on established turfgrass at the following specifications: spray volume: 400 L/ha; 2.58 Bar (AT)/1.3 km H using nozzles LU 90-02S Lechler gelb, adjuvant (0.2 % v/v non-ionic surfactant ("NIS") x77)). Rates tested included 12.5, 25, and 50 g ai/ha. Visual rating (%) of phytotoxicity and growth inhibition was done 7, 14, and 21 days after each application.

Example 1

Turf injury caused by the active compound of formula (I) on Agrostis stolonifera AGSST, Poa annua POAAN. In table 1, the time period for evaluation of the application is (DAA = days after application).

Table 1

g ai/ha AGSST POAAN

7DAA 25 25 53

50 65 65

14DAA 25 15 83

50 60 94

21DAA 25 3 82

50 48 94 Example 2

An outdoor trial was conducted with the active compound of formula (I) on an Agrostis stolonifera AGSST putting green contaminated with Poa annua POAAN. At trial initiation there was an average of 78.8 % POAAN in untreated plots. Two applications (Application 1 and Application 2) were applied in the spring on a 28 day interval. The compound of formula (I) was applied in combination with NIS (0.25% V:V). No phytotoxicity or injury was observed on the desirable AGST. Percent POAAN control was observed as follows (121 DAA1* and 93 DAA2+): Table 2

*DAA1 is Days After Application 1

+DAA2 is Days After Application 2

Example 3

An outdoor trial was conducted with the active compound of formula (I) on a Agrostis stolonifera AGSST putting green contaminated with Poa annua POAAN. At trial initiation there was an average of 91.3 % POAAN in untreated plots. Two applications (Application 1 and Application 2) were applied in the spring on a 28 day interval. The compound of formula (I) was applied in combination with a NIS (0.25% V:V). No phytotoxicity or injury was observed on the desirable AGST. Percent POAAN control was observed as follows (121 DAA1* and 93 DAA2+):

Table 3

*DAA1 is Days After Application 1

+DAA2 is Days After Application 2