WO2019209847A1 - Compositions et procédés de lutte contre la végétation indésirable dans des cultures - Google Patents

Compositions et procédés de lutte contre la végétation indésirable dans des cultures Download PDF

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Publication number
WO2019209847A1
WO2019209847A1 PCT/US2019/028752 US2019028752W WO2019209847A1 WO 2019209847 A1 WO2019209847 A1 WO 2019209847A1 US 2019028752 W US2019028752 W US 2019028752W WO 2019209847 A1 WO2019209847 A1 WO 2019209847A1
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Prior art keywords
herbicide
crops
undesirable vegetation
composition
crop
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PCT/US2019/028752
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English (en)
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WO2019209847A8 (fr
Inventor
Honwu HUANG
Demin SONG
Cong CONG
Youggui KU
Chungeng NI
Hao Long
Zengliang LI
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Fmc Corporation
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Priority to CN201980034968.7A priority Critical patent/CN112165862B/zh
Publication of WO2019209847A1 publication Critical patent/WO2019209847A1/fr
Publication of WO2019209847A8 publication Critical patent/WO2019209847A8/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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2

Definitions

  • the present disclosure relates to herbicidal compositions and methods for controlling undesirable vegetation in crops.
  • United States Patent 4,405,357 discloses certain 3-isoxazolidinones which exhibit desirable selective herbicidal activity. Specifically, such compounds are shown to be effective in controlling grassy and broadleaf weed species while leaving legumes, particularly soybeans, unaffected. Among the compounds specifically disclosed in this patent are 2-[(2,4-dichlorophenyl)methyl]-4,4- dimethyl-3-isoxazolidinone (CA No. 81777-95-9) and 2-[(2,5- dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone (CA No. 81778-66-7). Both such compounds are effective against a number of weeds.
  • crop protection products it is always desirable to increase the specific activity of active ingredients, provide resistance management, or broaden the scope of activity to include, for herbicidal compositions, control of additional weed species. Mixtures of crop protection agents are often used to provide such improved activity.
  • the present invention is directed to a herbicidal composition
  • a herbicidal composition comprising a first herbicide selected from the group consisting of 2-(2,4- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (“2,4-DC”), 2-(2,5- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (“2,5-DC”) and mixtures thereof; and a second herbicide that is isoproturon.
  • the present invention is directed to a method of controlling undesirable vegetation in a crop comprising applying to the locus of such vegetation an herbicidally-effective amount of a combination comprising a first herbicide selected from the group consisting of 2,4-DC, 2,5-DC and mixtures thereof, and a second herbicide that is isoproturon.
  • the present invention relates to a method for controlling undesirable vegetation in a crop comprising applying to the locus of such vegetation an herbicidally-effective amount of a combination comprising a first herbicide that is 2,4-DC and a second herbicide that is isoproturon, wherein said undesirable vegetation includes at least one of Alopecurus aequalis sobol (short-awn foxtail) and Sclerochloa dura (L.) P. Beauv (hardgrass, tufted hardgrass), and the crop is wheat.
  • Alopecurus aequalis sobol short-awn foxtail
  • Sclerochloa dura L.
  • Beauv hardgrass, tufted hardgrass
  • any number and any included range falling within the range is specifically disclosed.
  • every range of values (of the form,“from about a to about b,” or, equivalently,“from approximately a to b,” or, equivalently,“from approximately a— b”) disclosed herein is to be understood to set forth every number and range encompassed within the broader range of values.
  • ranges comtemplated may range from any of the enumerated lower limits to any of the enumerated upper limits.
  • compositions and methods are described in terms of “comprising,” “containing,” or“including” various components or steps, the compositions and methods can also“consist essentially of’ or“consist of’ the various components and steps. All numbers and ranges disclosed above may vary by some amount. Also, the terms in the claims have their plain, ordinary meaning unless otherwise explicitly and clearly defined herein. If there is any conflict in the usages of a word or term in this specification and one or more patent or other documents that may be incorporated herein by reference, the definitions that are consistent with this specification should be adopted.
  • the term “herbicide” refers to a composition mixture that is produced, sold, or used in a field in order to kill or otherwise inhibit the growth of unwanted plants such as, but not limited to, deleterious or annoying weeds, broadleaf plants, grasses, and sedges; and can be used for crop protection, edifice protection or turf protection.
  • the term“herbicide” includes the end-use herbicidal product.
  • This composition can be a pure compound, a solution of chemical compounds, a mixture of chemical compounds, an emulsion, a suspension, a solid-liquid mixture, or a liquid-liquid mixture.
  • herbicide also refers to the product that passes through the commercial channels from the manufacturer to the ultimate end user who can either apply the herbicide to the affected field as sold, or mix it with other excipients.
  • weed means and includes any plant that grows where not wanted.
  • herbicidally-effective amount means an amount of the composition or of the combinations according to the invention necessary to produce an observable herbicidal effect on unwanted plant growth, including one or more of the effects of necrosis, death, growth inhibition, reproduction inhibition, inhibition of proliferation, and removal, destruction, or otherwise diminishing the occurrence and activity of unwanted plants.
  • herbicidally active ingredient(s) refers to active ingredient(s) in the herbicide that causes the herbicide to prevent, destroy, repel or mitigate any weed.
  • Other ingredients of the herbicide that are not herbicidally active ingredients are excipients that aid in forming, storing, or delivering a herbicidally active ingredient to the target.
  • the term“herbicidal composition” refers to an herbicide, and in addition, to any composition that comprises an herbicidally active ingredient, such as those described herein, and optionally including at least one excipient. This composition can be a solution or a mixture.
  • herbicidal composition also refers to a product intended for use in manufacturing, or any product intended for formulation or repackaging into other agricultural products.
  • the composition includes any of the formulation types described below and also includes one or more formulations comprising the herbicidally active ingredients mixed with a diluent prior to application to the plants.
  • 2,4-DC refers to 2-[(2,4-dichlorophenyl)methyl]-4,4- dimethyl-3-isoxazolidinone.
  • 2,5-DC refers to 2-[(2,5-dichlorophenyl)methyl]-4,4- dimethyl-3-isoxazolidinone.
  • isoproturon refers to 3-(4-isopropylphenyl)-l,l-dimethylurea (i.e. L A -dimethyl-/V'-[4-(l-methylethyl)phenyl]urea (CA No. 34123-59-6)) .
  • At least one aspect of the present invention is directed to a herbicidal composition or combination comprising a first herbicide selected from the group consisting of 2,4-DC, 2,5-DC and mixtures thereof; and a second herbicide that is isoproturon.
  • the first herbicide is 2,4-DC.
  • the first herbicide is a mixture of 2,4-DC and 2,5-DC. If a mixture of 2,4-DC and 2,5-DC is employed, 2,4-DC and 2,5-DC can be present in any ratios. In a specific embodiment, 2,4-DC is present in excess of 2,5-DC.
  • the second herbicide in the composition or combination is isoproturon. It is a photosystem II photosynthesis inhibitor.
  • compositions of the present invention can further contain a third herbicide.
  • the third herbicide does not interfere with the synergistic effect between the first herbicide and the second herbicide.
  • a third herbicide may be utilized if broadening of the spectrum of weed control or preventing the occurrence of resistance is desirable.
  • Example of useful additional herbicides include but are not limited to acetochlor, aclonifen, ametryn, amicarbazone, atrazine, bispyribac, beflubutamid, S- beflubutamid, bromoxynil, carfentrazone, carfentrazone ethyl, cyhalofop, 2,4-D, 2,4-DB, 2,4-DEB, dicamba, diflufenican, dimethachlor, dimethenamid-P, ethalfluralin, ethoxysulfuron, flucetosulfuron, fluthiacet-methyl, fomesafen, hexazinone, isoxaflutole, linuron, mesotrione, metamifop, metazachlor, metobromuron, S-metolachlor, metribuzin, metsulfuron, metsufluron-methyl, napropamide, pendimethalin, pethoxa
  • said third herbicide is selected from the group consisting of napropamide, aclonifen, pyroxasulfone, metazachlor, diflufenican, sulfentrazone, mesotrione, metsulfuron, thifensulfuron, thifensulfuron-methyl and agriculturally acceptable salts thereof, esters thereof and mixtures of two or more thereof.
  • the composition of the invention can also include a herbicide safener selected from the group consisting of allidochlor, benoxacor, cloquintocet-mexyl, cumyluron, cyometrinil, cyprosulfonamide, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, methoxyphenone naphthalic anhydride (l,8-naphthalic anhydride), oxabetrinil, N-(aminocarbonyl)-2-methylbenzenesulfonamide, N-(aminocarbonyl)-2 fluorobenzenesulfonamide, 1 -bromo-4- [(chloro-methyl)-sulf
  • the present invention relates to a method of controlling undesirable vegetation in a crop comprising applying to the locus of such vegetation a combination comprising a first herbicide selected from the group consisting of 2,4-DC, 2,5-DC and mixtures thereof; and a second herbicide that is isoproturon.
  • a combination comprising a first herbicide selected from the group consisting of 2,4-DC, 2,5-DC and mixtures thereof; and a second herbicide that is isoproturon.
  • the combination can be applied as a single composition, or as separate compositions.
  • said undesirable vegetation includes at least one selected from the group consisting of grass weeds and broadleaf weeds.
  • said vegetation is selected from the group consisting of annual bluegrass, Benghal dayflower, blackgrass ( Alopecurus myosuroides), black nightshade, broadleaf signal grass, Canada thistle, cheat, common cocklebur (Xanthium pensylvanicum), common ragweed, corn poppies, field violet, giant foxtail, goosegrass, green foxtail, guinea grass, hairy beggarticks, herbicide- resistant blackgrass, horseweed, Italian rye grass, jimsonweed, Johnson grass (Sorghum halepense), large crabgrass, little seed canary grass, morning glory, Pennsylvania smartweed, pitted morning glory, prickly sida, quackgrass, redroot pigweed, shattercane, shepherd’s purse, silky windgrass, sunflower (as a weed in potato crops), wild buckwheat (Polygonum
  • said undesirable vegetation includes at least one of Alopecurus aequalis sobol, Sclerochloa dura (L.) P. Beauv. Alopecurus japonicus, Myosoton aquaticum, Stellaria media, Beckmannia, and syzigachne.
  • said undesirable vegetation includes at least one of Alopecurus aequalis sobol, Sclerochloa dura (L.) P. Beauv., Alopecurus japonicus, Myosoton aquaticum, Stellaria media, and Beckmannia syzigachne that is growing in wheat ( Triticum aestivum).
  • the crop is selected from the group consisting of broadleaf crops and grass.
  • the crop includes bananas, beans, beets, cassava, cereals, citrus, cocoas, coconuts, coffee, corn, cotton, fiber crops, flowers, forage corps, forestry, groundnuts, peanuts, hops, horticultures, non-land crops, oil palm, oilseed rape, peas, pomes, potato, rice, stonefruit, spices, sugar cane, sunflower, tea, tobacco, tomatoes, tree nuts, turf, vegetable crops, vines, and grapes.
  • the crops are potato, soybean, corn, rice, sorghum, oilseed rape, barley, rye, cowpea or canola.
  • the crop is wheat.
  • the present invention relates to a method of controlling undesirable vegetation in a crop, comprising applying to the locus of such vegetation a combination comprising a first herbicide selected from the group consisting of 2,4-DC, 2,5-DC and mixtures thereof; and a second herbicide that is isoproturon, wherein said vegetation includes at least one of Alopecurus aequalis sobol and Sclerochloa dura (L.) P. Beauv, and the crop is wheat.
  • a first herbicide selected from the group consisting of 2,4-DC, 2,5-DC and mixtures thereof
  • a second herbicide that is isoproturon wherein said vegetation includes at least one of Alopecurus aequalis sobol and Sclerochloa dura (L.) P. Beauv, and the crop is wheat.
  • compositions containing the active compounds/ingredients of the present invention may be employed in any conventional agriculturally useful form, for example, in the form of a twin pack, or in a ready-to-use formulation, or in the form of a tank mix.
  • the active compounds can be supplied (either separately or pre-mixed) in any appropriate formulation type, for example an emulsifiable concentrate (EC), a suspension concentrate (SC), a suspo- emulsion (SE), a capsule suspension (CS), a water dispersible granule (WG), an emulsifiable granule (EG), a water in oil emulsion (EO), and oil in water emulsion (EW), an oil dispersion (OD), an oil miscible flowable (OF), an oil miscible liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra- low volume liquid (UL), a dispersible concentrate (DC), a wettable powder (WP) or any other technically
  • compositions can be formulated using excipients and formulation techniques that are known in the art for individually formulating the herbicides.
  • the herbicides may be mixed together, optionally with other formulating ingredients.
  • the active ingredients of the compositions may be provided in a single formulation, or in tank-mix form where the active ingredients are each provided in a separate formulation that are tank mixed, typically with a diluent such as water, prior to application.
  • the active ingredients are preferably co-formulated and provided in a single formulation to provide a more convenient application, and more preferably provided in a formulation type, for instance, WP, WG, SC, EC, or CS formulation.
  • the active ingredients of the compositions may be encapsulated or non- encapsulated. Encapsulation is usually used to reduce the volatility of the herbicide or provide slow release of the herbicide.
  • the first herbicide of the compositions is encapsulated (e.g. encapsulation of 2,4-DC, 2,5-DC or both), with the second herbicide being non-encapsulated.
  • compositions When mixed with additional components, the compositions typically contain about 0.01 to about 95% by weight of active compounds, while the rest typically are excipients for formulating the herbicides, for instance diluents, surfactants and the like.
  • diluent includes all liquid and solid agriculturally acceptable material including carriers which may be added to the herbicides to bring them in a suitable application or commercial form and include solvents, emulsifiers, and dispersants.
  • the diluent may be added during the formulation process, after the formulation process (e.g. by the user - a farmer or custom applicator), or both.
  • suitable solid diluents or carriers are aluminum silicate, talc, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, absorbent carbon black, chalk, silica, and clays such as kaolin and bentonite.
  • suitable liquid diluents include water, organic solvents (e.g.
  • acetophenone cyclohexanone, isophorone, toluene, xylene, petroleum distillates), amines (e.g. ethanolamine, dimethylformamide), and mineral, animal, and vegetable oils (used alone or in combination).
  • amines e.g. ethanolamine, dimethylformamide
  • mineral, animal, and vegetable oils used alone or in combination.
  • compositions may also contain surfactants, protective colloids, thickeners, penetrating agents, stabilizers, sequestering agents, anti-caking agents, coloring agents, corrosion inhibitors, and dispersants such as lignosulfite waste liquors and methylcellulose.
  • surfactant as used herein, means an agriculturally acceptable material which imparts emulsifiability, stability, spreading, wetting, dispersibility or other surface-modifying properties.
  • suitable surfactants include lignin sulfonates, fatty acid sulfonates (e.g.
  • lauryl sulfonate the condensation product of formaldehyde with naphthalene sulfonate, alkylarylsulfonates, ethoxylated alkylphenols, and ethoxylated fatty alcohols.
  • Other known surfactants that have been used with herbicides are also acceptable.
  • compositions may be applied in various combinations of the active ingredients. For example, they may be applied as a single“ready-mix” form, or in a tank mix form. Thus, to be used in combination, it is not necessary that the active ingredients are applied in a physically combined form, or even at the same time. In other word, the active ingredients may be applied separately and/or sequentially, provided that the application of the second active compound occurs within a reasonable period of the time from the application of the first active compound, such as within 24 hours, or 48 hours.
  • the compositions may be applied post-emergence. In a preferred embodiment, the compositions are applied early post-emergence. In a specific embodiment, the compositions of the present invention are applied to protect wheat at the four-leaf stage of wheat.
  • Rates of the application of the composition will vary according to a number of factors such as targeted weeds, degree of infestation, weather conditions, soil conditions, crop species, mode of application, and time of application.
  • the weight ratio of the first herbicide and the second herbicide is preferably selected to provide synergistic weed control. Such amounts are also called synergistically effect amounts and can easily be determined by the skilled person using well known principles.
  • the weight ratio of the first herbicide (for instance, 2,4-DC or 2,5-DC) and the second herbicide (i.e., isoproturon) ranges from 1: 1 to 1:20, 1 : 1 to 1 : 15, or 1: 1 to 1: 10.
  • an effective amount of the combination of the first herbicide and the second herbicide is any amount that has the ability to combat the undesirable vegetation.
  • the first herbicide for instance, 2,4-DC or 2,5-DC
  • the second herbicide i.e., isoproturon
  • the second herbicide is employed in an amount from a lower limit of 1,500 or 1,000 g a.i./ha to an upper limit of 2,000, 2,500 or 4,000 g a.i./ha, preferably from 500 to 2,500 g a.i./ha, such as from 750 to 1,125 g a.i./ha.
  • higher and in particular lower doses may also provide adequate control.
  • An additional herbicide may be also used, provided that the additional herbicide does not interfere with the synergistic effect between the first herbicide and the second herbicide.
  • An additional herbicide may be utilized if broadening the spectrum of control or preventing the build-up of resistance is desired. Examples of additional herbicides useful in the present invention include but are not limited to those discussed above.
  • Synergy was calculated using the method of Colby.
  • the terms“synergy” and“synergistic”, or the phrase“in a synergistic manner” refer to the in vivo interaction of two or more biologically active compounds, in the present case the first herbicide with the second herbicide, so that their combined effect when administered together is greater than the sum of the effects observed when each is administered individually. In this way the applied rate of the herbicidal combination can be lower than the registered use rates, thereby reducing the total chemical burden on the field to which such a combination is applied.
  • ‘X’ is the herbicidal activity in percentage control of the disclosed 3- isoxazolidinone applied as a mixture at rate‘x’.
  • the ⁇ term is the herbicidal activity of the second active (isoproturon) applied as a mixture at rate‘y’.
  • the equation calculates ⁇ ’, the “expected” herbicidal activity of the mixture of ‘X’ at rate‘x’ with‘Y’ at rate ‘y’. If ⁇ ’ is lower than the observed activity, synergy is present. If the herbicidal effect is strictly additive and no interaction has occurred, ⁇ ’ will be equal to or higher than the observed activity.
  • Step B i.e. containing unreacted 4,4-dimethylisoxazolidin-3-one sodium salt, 2,4-dichlorobenzyl chloride and (9-alkylated side product, 3-[(2,4-dichlorophenyl)methoxy]-4,5-dihydro-4,4- dimethylisoxazole)
  • methanol i.e. containing unreacted 4,4-dimethylisoxazolidin-3-one sodium salt, 2,4-dichlorobenzyl chloride and (9-alkylated side product, 3-[(2,4-dichlorophenyl)methoxy]-4,5-dihydro-4,4- dimethylisoxazole
  • methanol i.e. containing unreacted 4,4-dimethylisoxazolidin-3-one sodium salt, 2,4-dichlorobenzyl chloride and (9-alkylated side product, 3-[(2,4-dichlorophenyl)methoxy]-
  • An SC formulation of 2,4-DC was prepared by combining 44.0% 2,4-DC, 1.5% TERGITOLTM XD (Dow Chemical Company), ETHOX ERS 01293 (Ethox Chemicals), 6.0% propyleneglycol, 0.13% of a 2% aqueous solution of KELZAN ® M xanthan gum (CPKelco A Huber Company), 0.15% DOW AF antifoam (Dow Chemical Company) and 46.7% water (all % by weight) and milling the mixture until a particle size of D90 (90% of the particles have a diameter) less than about 50 microns was obtained.
  • Mixtures of 2,4-DC and isoproturon were provided in a tank-mix form by mixing the SC formulation of 2,4-DC and the 50% WP formulation of isoproturon prior to use.
  • compositions described above were tested for herbicidal efficacy.
  • the test crop was wheat, and the test weeds were Alopecurus aequalis sobol and Sclerochloa dura (L.) P. Beauv.
  • wheat was planted in a field with the targeted weeds naturally occurring and well watered before the application of the compositions.
  • the test compositions were applied by spray application individually and in combination at the rates indicated at the four-leaf stage of wheat, and the control of weeds was assessed at a certain day after treatment (DAT) as indicated in Tables 1 and 2 below.
  • DAT day after treatment
  • X g and Xi is the number of weeds pre-treatment and post- treatment in a same area, respectively

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Catching Or Destruction (AREA)

Abstract

La présente invention concerne des compositions herbicides comprenant un premier herbicide choisi dans le groupe constitué par 2,4-DC, 2,5-DC et leurs mélanges, et un second herbicide qui est l'isoproturon ; et des procédés de lutte contre la végétation indésirable dans des cultures, comprenant l'application d'une combinaison du premier herbicide et du second herbicide au locus de la végétation.
PCT/US2019/028752 2018-04-24 2019-04-23 Compositions et procédés de lutte contre la végétation indésirable dans des cultures WO2019209847A1 (fr)

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US201862661766P 2018-04-24 2018-04-24
US62/661,766 2018-04-24

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EP3971170A4 (fr) * 2019-05-13 2022-05-25 Zhejiang Zhuji United Chemicals Co., Ltd Forme cristalline thermostable de haute pureté de composé 3-isoxazolidinone substitué, son procédé de préparation et son application

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CN113135868A (zh) * 2021-04-07 2021-07-20 浙江禾本科技股份有限公司 一种高含量异恶草酮的制备方法

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WO2017025418A1 (fr) * 2015-08-07 2017-02-16 Bayer Cropscience Aktiengesellschaft Nouvelles utilisations de 2-(2,4-dichlorophényl)méthyl-4,4-diméthyl-3-isoxazolidone comme herbicide foliaire
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CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 107746-05-4
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Publication number Priority date Publication date Assignee Title
EP3971170A4 (fr) * 2019-05-13 2022-05-25 Zhejiang Zhuji United Chemicals Co., Ltd Forme cristalline thermostable de haute pureté de composé 3-isoxazolidinone substitué, son procédé de préparation et son application

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AR114836A1 (es) 2020-10-21
CN112165862A (zh) 2021-01-01
WO2019209847A8 (fr) 2020-12-17

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