WO2019006358A1 - Composition herbicide et son procédé d'utilisation - Google Patents

Composition herbicide et son procédé d'utilisation Download PDF

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Publication number
WO2019006358A1
WO2019006358A1 PCT/US2018/040383 US2018040383W WO2019006358A1 WO 2019006358 A1 WO2019006358 A1 WO 2019006358A1 US 2018040383 W US2018040383 W US 2018040383W WO 2019006358 A1 WO2019006358 A1 WO 2019006358A1
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WIPO (PCT)
Prior art keywords
compound
formula
turf grass
poa annua
turf
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PCT/US2018/040383
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English (en)
Inventor
Louis Simard
John Robert James
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Syngenta Participations Ag
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Publication of WO2019006358A1 publication Critical patent/WO2019006358A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the compound 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2- one is a dihydro-hydantoin having known herbicidal activity as shown, for example, in WO 2015/059262.
  • 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.
  • 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):
  • 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.
  • a herbicidally effective amount of the compound of formula (I) i.e., 4-hydroxy-l-methyl-3-[4- (trifluoromethyl)-2-pyridyl]imidazolidin-2-one
  • 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.
  • 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.
  • 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.
  • 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.
  • 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).
  • the term 'herbicide' as used herein denotes a compound which controls or modifies the growth of undesired plants, in particular Poa annua.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • a rate of between 12.5 and 25g a.i./ha is preferred.
  • 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.
  • an application rate on an annual loading basis of between about 50 and about 300g a.i./ha is suitable.
  • a rate of an application rate on an annual loading basis of between about 50 and about 200g a.i./ha is preferred.
  • 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.
  • 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.
  • 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]imidazolidin-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.
  • the cumulative annual rate is achieved by 4 applications in the fall and 4 applications in the spring.
  • the weed species to be controlled by the inventive method is Poa annua or Annual bluegrass (also called annual meadow grass).
  • 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
  • the 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-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.
  • 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.
  • 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.
  • 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.
  • the method of the invention provides that 4- hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one can be safely applied to such dormant bermudagrass and provide acceptable weed control of Poa annua.
  • the method for selectively controlling or modifying the growth of actively growing Poa annua in dormant bermudagrass 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.
  • 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
  • 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).
  • 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.
  • a phytotoxicity evaluation is made 120 days after application of the compound of formula (I)..
  • suitable cool-season and warm season turf grass is understood to include creeping bentgrass (Agrostis stolonifera) or bermudagrass (Cynodon dactylon).
  • 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.
  • 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.
  • compositions which contain 4-hydroxy-l-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-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.
  • the method of the invention is practiced as a pre-emergent Poa annua control application.
  • the method of the invention is practiced as a post-emergent Poa annua control application.
  • the rate and interval embodiments for the method as mentioned above are also valid for the pre-emergence control of Poa annua.
  • 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.
  • 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.
  • 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:
  • Herbicides such as:
  • Methiozolin (oxazole herbicide chemistry); Cinmethylin (unclassified herbicide chemistry)
  • Trifloxysulfuron, metsulfuron, chlorsulfuron, halosulfuron, foramsulfuron, rimsulfuron, sulfosulfuron, flazasulfuron, iodosulfuron, and orthosulfamuron (Sulfonylureas herbicide chemistries).
  • imidazolinone herbicide chemistry examples include imazapyr.imaziquin, imazapyr and imazapic;
  • triazolopyrimide herbicide chemistry examples include cloransulam-methyl, florasulam, flumetsulam, penoxsulam;
  • pyrimidinyl benzoate herbicide chemistry examples 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
  • Carfentrazone-ethyl and sulfentrazone (Triazolinone herbicide chemistry); Butafenacil (Pyrimidindione herbicide chemistry);
  • Indaziflam Alkylazine herbicide chemistry
  • Dicamba (Benzoic Acid herbicide chemistry)
  • Oxadiazon (Oxadiazole herbicide chemistry)
  • Glufosinate-ammonium Phosphinic herbicide chemistry
  • Fungicides such as:
  • Triazoles includings propiconazole, difenoconazole, cyproconazole, triticonazole, metconazole, triadimefon and tebuconazole;
  • SDHIs including - boscalid, fluopyram, fluxapyroxad, isopyrazam, penthiopyrad, SolatenolTM; Adepidyn,
  • 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.
  • Insecticides and nematicides such as: thiamethoxam, imidacloprid, abamectin, milbamectin, permethrin, lambda cyhalothrin, cypermethrin, bifenthrin , fipronil, chlorotraniliprole, cyantraniliprole and fluopyram.
  • Soil Wetting Agents such as: alkyl polyglycosides (APG) and ethylene oxide- propylene oxide (EO/PO) block copolymer surfactants.
  • APG alkyl polyglycosides
  • EO/PO ethylene oxide- propylene oxide
  • Plant Growth Regulators (PGRs): uniconazole and paclobutrazol (azole PGR
  • 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
  • PGR plant growth regulator
  • the method of invention comprises use of a PGR selected from paclobutazol.
  • suitable rates for palobutrazol are an annual application rate: from 1 to 2,241 g ai/ha/yr.
  • the per application rate of paclobutrazol within the method herein is: 30 to 840 gai/ha and more specifically 73 to 292g ai/ha.
  • 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.
  • 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.
  • all the components are administered within a timescale of a few hours, such as one hour.
  • 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.
  • 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.
  • 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).
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • the compound of formula (I) is impregnated on controlled release fertilizer granules: Impregnation on granules: polymer-coated (PolyonTM, DurationTM, ESNTM), polymer-coated sulfur coated (poly-STM), sulfur-coated (SCU), resin- coated (OsmocoteTM) or are impregnated on other granules such as palletized limestone, corncobs, clay, paper, and peanut hulls.
  • Impregnation on granules polymer-coated (PolyonTM, DurationTM, ESNTM), polymer-coated sulfur coated (poly-STM), sulfur-coated (SCU), resin- coated (OsmocoteTM) or are impregnated on other granules such as palletized limestone, corncobs, clay, paper, and peanut hulls.
  • 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.
  • 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.
  • 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.
  • compositions 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.
  • 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.
  • 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.
  • 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, ⁇ , ⁇ -dimethyl formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate
  • 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.
  • 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.
  • 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.
  • 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.
  • suitable safeners there may be mentioned: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and
  • 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.).
  • 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.
  • Dust and liquid compositions 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.
  • 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.
  • 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.
  • 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).
  • 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.

Abstract

La présente invention concerne un procédé de commande ou modification sélective de la croissance de Poa annua dans l'agrostide rampant (Agrostis stolonifera) ou le cynodon dormant (Cynodon dactylon) sans causer des dommages significatifs à un tel gazon, comprenant l'application au gazon ou à l'habitat de Poa annua dans un tel gazon, d'une quantité herbicide efficace d'une composition comprenant un composé de formule (I).
PCT/US2018/040383 2017-06-30 2018-06-29 Composition herbicide et son procédé d'utilisation WO2019006358A1 (fr)

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EP17179126 2017-06-30

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4604127A (en) * 1984-07-17 1986-08-05 Eli Lilly And Company Herbicidal pyridazinylimidazolidinone compounds
US20160251332A1 (en) * 2013-10-25 2016-09-01 Syngenta Participations Ag Herbicidal Compounds
US20160264547A1 (en) * 2013-10-07 2016-09-15 Syngenta Participations Ag Herbicidal Compounds
WO2018015180A1 (fr) * 2016-07-20 2018-01-25 Basf Se Compositions herbicides comprenant des phénylpyrimidines
WO2018065311A1 (fr) * 2016-10-07 2018-04-12 Syngenta Participations Ag Mélanges herbicides

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4604127A (en) * 1984-07-17 1986-08-05 Eli Lilly And Company Herbicidal pyridazinylimidazolidinone compounds
US20160264547A1 (en) * 2013-10-07 2016-09-15 Syngenta Participations Ag Herbicidal Compounds
US20160251332A1 (en) * 2013-10-25 2016-09-01 Syngenta Participations Ag Herbicidal Compounds
WO2018015180A1 (fr) * 2016-07-20 2018-01-25 Basf Se Compositions herbicides comprenant des phénylpyrimidines
WO2018065311A1 (fr) * 2016-10-07 2018-04-12 Syngenta Participations Ag Mélanges herbicides

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