WO2025181802A1 - Compositions herbicides à base d'aminopyralide et leurs utilisations - Google Patents

Compositions herbicides à base d'aminopyralide et leurs utilisations

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Publication number
WO2025181802A1
WO2025181802A1 PCT/IL2025/050191 IL2025050191W WO2025181802A1 WO 2025181802 A1 WO2025181802 A1 WO 2025181802A1 IL 2025050191 W IL2025050191 W IL 2025050191W WO 2025181802 A1 WO2025181802 A1 WO 2025181802A1
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WIPO (PCT)
Prior art keywords
alkyl
dmso
mixture
based surfactant
herbicidal formulation
Prior art date
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Pending
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PCT/IL2025/050191
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English (en)
Inventor
Augusto Cesar GONCALVES
Tiago Elias DA SILVA
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Adama Agan Ltd
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Adama Agan Ltd
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Publication of WO2025181802A1 publication Critical patent/WO2025181802A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the present invention provides herbicidal formulations comprising aminopyralid in its free acid form; a solvent combination comprising dimethyl sulfoxide (DMSO) and an additional solvent selected from an amide-based solvent; a ketone-based solvent; and a mixture thereof; and a surfactant.
  • DMSO dimethyl sulfoxide
  • the formulations of the invention are useful in controlling weed.
  • a herbicide in order for a herbicide to reach its site of action within a plant, it must cross several barriers such as the cell wall, the cell membrane (plasma membrane), and optionally organellar membranes within the plant cell. The herbicide then accumulates at its site of action and causes phytotoxicity, i.e., negative effects on plant growth.
  • the passive absorption of a herbicide into a cell and its accumulation within the cell are both controlled by the physiochemical characteristics of the herbicide, more specifically its lipophilicity (ability to dissolve in lipids) and acidity properties.
  • herbicides having ionizable groups vary in their ability to cross lipophilic membranes. For instance, herbicides that are uncharged are more lipophilic and therefore able to cross a lipid bilayer more readily. In contrast, charged herbicides are more hydrophilic and therefore will traverse a lipid bilayer more slowly.
  • oil-based formulations may have advantageous biological efficacy since these types of formulations contain active ingredient(s), organic solvent(s) and surfactant(s); and may further comprise agricultural excipients such as oil-based adjuvants. These excipients may improve the absorption of the active ingredient(s) by the weed(s) and enable to use lower doses of active ingredient per hectare compared to other types of formulations.
  • the EC formulations create an oil-in-water emulsion when added to the spray tank, offer spontaneous emulsification on dilution, and deliver uniform application of the active ingredient(s).
  • WO 2011/094388 A2 discloses the use of tank mixes of commercially available soluble granules of aminopyralid tri- isopropanol ammonium salt and commercially available water dispersible granules comprising 2,4-D dimethyl amine, in rice.
  • oil-based formulations comprising active ingredient(s) which has an ionizable group such as a carboxylic acid group, more specifically aminopyralid, wherein said ionizable group is in its neutral form, such as in its free acid form.
  • an ionizable group such as a carboxylic acid group, more specifically aminopyralid
  • aminopyralidbased formulations wherein the aminopyralid is in the form of its free acid, which comprise a solvent combination comprising DMSO and an additional solvent selected from an amide- based solvent, a ketone-based solvent, and a mixture thereof, specifically wherein said additional solvent is A A-di methyl decanamide, A-butyl-2-pyrrolidone (NBP), or acetophenone; and a surfactant, were stable even under accelerated storage conditions.
  • the present invention thus provides an herbicidal formulation comprising: (i) aminopyralid in the form of a free acid; (ii) a solvent combination comprising dimethyl sulfoxide (DMSO) and an additional solvent selected from an amide-based solvent; a ketone-based solvent; and a mixture thereof; and (iii) a surfactant.
  • DMSO dimethyl sulfoxide
  • said solvent combination comprises DMSO and an additional solvent selected from A-(Ci-Cs)alkyl pyrrolidone, preferably A-(Ci-Cs)alkyl-2- pyrrolidone; an amide of the formula R-C(O)-N-((Ci-C4)alkyl)2, wherein R is (C?-Ci3)alkyl optionally substituted, preferably at position a to the amide group, with a substituent selected from -OH, -O-(Ci-Ce)alkyl, -CN, and -NO2; a ketone of the formula R’-CO-R’, wherein R’ each independently is (Ci-Ce)alkyl, phenyl, or heteroaryl such as pyridyl, imidazolyl, and pyrimidinyl, or two of the R’s together with the carbon atom to which they are attached form a 5-7 membered ring; and
  • the present invention relates to methods for using an herbicidal formulation as defined above, i.e., an EC formulation containing aminopyralid in its free acid form.
  • an herbicidal formulation as defined above i.e., an EC formulation containing aminopyralid in its free acid form.
  • a method of controlling pest such as a weed, comprising applying to a locus where control of said pest is desired, such as a field of crop, an effective amount of a formulation as defined herein.
  • an herbicidal formulation comprising: (i) aminopyralid in the form of a free acid thereof, i.e., wherein its carboxylic acid group is in its free acid form; (ii) a solvent combination comprising DMSO and an additional solvent selected from an amide-based solvent; a ketone-based solvent; and a mixture thereof; and (iii) at least one surfactant.
  • Aminopyralid (4-amino-3,6-dichloropyridine-2-carboxylic acid) is a synthetic auxin in the pyridine carboxylic acid class of herbicides.
  • Auxins are plant hormones that regulate several plant activities, including development of the plant embryo, leaf formation, phototropism, gravitropism, apical dominance, fruit development, abscission, and root initiation. Auxins are actively transported into cells by a transmembrane transporter protein and leave the cells by facilitated diffusion through a different transporter. Based on studies of various auxin analogues, it was postulated that the import mechanism allows auxinic herbicides into the cell, but they cannot leave the cell through the exporter.
  • auxinic herbicides include alteration in cell wall elasticity and gene expression. Additionally, non-productive tissue growth if often induced, resulting in epinasty and phloem disruption, preventing the movement of photosynthate and causing death in days to weeks.
  • Aminopyralid provides systemic postemergence broad-spectrum control of several key noxious and invasive annual, biennial and perennial weed species, as well as agronomic broadleaf weeds. Aminopyralid can also provide residual weed control activity controlling re-infestations and reducing the need for re-treatment depending on the rate applied and the target weeds.
  • Particular amide-based solvents referred to herein are those of the formula V-(Ci- Cs)alkyl pyrrolidone, e.g., 7V-(Ci-Cs)alkyl-2-pyrrolidone.
  • Non-limiting examples of solvents of the formula 7V-(Ci-Cs)alkyl-2-pyrroli done include N-butyl-2-py rroli done (NBP).
  • amide-based solvents referred to herein are those of the formula R-C(O)-N-((Ci-C4)alkyl)2, e.g., R-C(O)-N-(CHa)2, wherein R is (C?-Ci3)alkyl optionally substituted, preferably at position a to the amide group, with a substituent selected from - OH, -O-(Ci-Ce)alkyl, -CN, -NO2, and a mixture thereof.
  • Non-limiting examples of solvents of the formula R-C(O)-N-((Ci-C4)alkyl)2 include N, -di methyl decanamide.
  • Particular ketone-based solvents referred to herein are those of the formula R’-CO- R’, wherein R’ each independently is (Ci-Ce)alkyl, phenyl, or heteroaryl such as pyridyl, imidazolyl, and pyrimidinyl, or two of the R’s together with the carbon atom to which they are attached form a 5-7 membered ring.
  • R’ each independently is (Ci-Ce)alkyl, phenyl, or heteroaryl such as pyridyl, imidazolyl, and pyrimidinyl, or two of the R’s together with the carbon atom to which they are attached form a 5-7 membered ring.
  • Non-limiting examples of solvents of the formula R’-CO-R’ include acetophenone (wherein one of R’ is phenyl and the other R’ is methyl).
  • alkyl typically means a linear or branched hydrocarbyl having, e.g., 1- 13 carbon atoms and includes, e.g., methyl, ethyl, w-propyl, isopropyl, //-butyl, sec-butyl, isobutyl, tert-butyl, w-pentyl, 2,2-dimethylpropyl, w-hexyl, w-heptyl, w-octyl, w-decanyl, and the like.
  • (Ci-Ci2)alkyls or (Ci-Cio)alkyls are preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, and w-decanyl.
  • the alkyl may optionally be substituted by one or more group s/substituents each independently selected from, e.g., -OH, -O-(Ci- Ce)alkyl, -CN, and -NO2.
  • the ratio between the DMSO and the additional solvent(s) composing the solvent combination referred to herein is from about 30: 1 to about 1 :30, e.g., from about 25: 1 to about 1 :20, from about 20: 1 to about 1 : 10, from about 15: 1 to about 1 :5, about 15: 1, about 10:1, about 5: 1, about 1 : 1, about 1 :2, about 1 :3, about 1 :4, or about 1 :5, respectively, by weight.
  • the solvent combination comprises DMSO and an 7V-(Ci-Cs)alkyl-2-pyrrolidone such as 7V-butyl-2-pyrrolidone (NBP), as an additional solvent; and/or the weight ratio between the DMSO and the additional solvent is from 20: 1 to about 5: 1, e.g., from about 18: 1 to about 7: 1, from about 16: 1 to about 9: 1, from about 14: 1 to about 11 : 1, about 20: 1, about 19: 1, about 18: 1, about 17: 1, about 16: 1, about 15: 1, about 14: 1, about 13: 1, about 12: 1, about 11 : 1, about 10: 1, about 9: 1, about 8: 1, about 7: 1, about 6: 1, or about 5: 1, respectively.
  • NBP 7V-butyl-2-pyrrolidone
  • the solvent combination comprises DMSO and an amide of the formula R-C(O)-N-((Ci-C4)alkyl)2 such as N,N- dimethyl decanamide, as an additional solvent; and/or the weight ratio between the DMSO and said additional solvent is from about 2: 1 to about 1 :5, e.g., from about 1.5: 1 to about 1 :3, from about 1 : 1 to about 1 :2, about 2: 1, about 1.5: 1, about 1 : 1, about 1 : 1.5, about 1 :2, about 1 :3, about 1 :4, or about 1 :5 respectively.
  • the solvent combination comprises DMSO and a ketone of the formula R’-CO-R’ such as acetophenone (wherein one of R’ is phenyl and the other R’ is methyl), as an additional solvent; and/or the weight ratio between the DMSO and the additional solvents is from 20: 1 to about 5:1, e.g., from about 18: 1 to about 7:1, from about 16: 1 to about 9: 1, from about 14: 1 to about 11 :1, about 20: 1, about 19: 1, about 18: 1, about 17: 1, about 16: 1, about 15: 1, about 14: 1, about 13:1, about 12: 1, about 11 : 1, about 10: 1, about 9: 1, about 8: 1, about 7:1, about 6: 1, or about 5: 1, respectively.
  • R’-CO-R such as acetophenone (wherein one of R’ is phenyl and the other R’ is methyl)
  • the weight ratio between the DMSO and the additional solvents is from 20: 1 to about 5:1, e.g.,
  • the at least one, e.g., one, two, three, four, or more, surfactant(s) comprised within the formulation of the present invention according to any one of the embodiments above, each independently, is selected from a dialkyl sulfosuccinate salt-based surfactant, an ethoxylated castor oil (e.g., Surfom® R 400 and Surfom® R 200), an alkyl benzene sulfonate salt-based surfactant (e.g., NINATE® 70B), a tri styrylphenol ethoxylate phosphate ester-based surfactant (e.g., Soprophor® 3D33), and a trialkyl amine oxide-based surfactant (e.g., lauryl dimethylamine N-oxide such as Steprow® GP 103).
  • a dialkyl sulfosuccinate salt-based surfactant e.g., an ethoxylated castor oil (e.
  • surfactant refers to any agriculturally acceptable material which imparts or improves emulsifiability, spreading, wetting, dispersibility, or other surfacemodifying properties of a herbicidal formulation, and optionally stability of said formulation, e.g., by inhibiting crystal growth or avoiding particle agglomeration.
  • dialkyl sulfosuccinate salt-based surfactants referred to herein are those comprising a di-(C?-Ci2)alkyl sulfosuccinate alkali metal salt or a di-(C?-Ci2)alkyl sulfosuccinate alkaline earth metal salt.
  • di-(C?-Ci2)alkyl sulfosuccinate alkali metal salts include sodium dioctyl sulfosuccinate (e.g., Aerosol® OT- 75 and Aerosol® OT-100).
  • alkali metal refers to the chemical elements lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr). Together with hydrogen they constitute group 1, which lies in the s-block of the periodic table and they readily lose their outermost electron to form cations with charge +1.
  • alkaline earth metal refers to six chemical elements in group 2 of the periodic table, i.e., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra).
  • Be beryllium
  • Mg magnesium
  • Ca calcium
  • Ba barium
  • Ra radium
  • the herbicidal formulation of the invention further comprises at least one, e.g., one, two, three, four, or more, agriculturally acceptable excipient(s) such as a stabilizer, an anti-freeze agent, a dispersant, a biocide, an anti-foaming agent, and a thickener.
  • agriculturally acceptable excipient(s) such as a stabilizer, an anti-freeze agent, a dispersant, a biocide, an anti-foaming agent, and a thickener.
  • agriculturally acceptable excipient refers to an essentially inert substance that can be used as a diluent and/or carrier for an active agent in a composition for treatment of plants and/or plant parts.
  • the formulation of the present invention comprises aminopyralid in the form of its free acid as an herbicide and further comprises one or more, e.g., one, two, three, four, or more, additional herbicide(s), wherein said at least one additional herbicide is a synthetic auxin (also referred to herein as “ aminopyralid-additional herbicide(s)-based formulation )
  • HRAC Herbicide Resistance Action Committee
  • group of synthetic auxin herbicides that mimic the activity of the plant hormone auxin (indole-3- acetic acid, IAA).
  • IAA indole-3- acetic acid
  • Synthetic auxins are most commonly used to control broadleaf weeds in small grain cereals, fallow, and rangeland systems, although some are used to control grass and sedge species (Todd et al., 2020).
  • the at least one additional herbicide comprised within the aminopyralid-additional herbicide(s)-based formulations of the present invention is one or more synthetic auxin herbicide(s) each independently selected from 2,4-D, fluroxypyr, and triclopyr, and said at least one additional herbicide is in the form of a free acid, salt, ester, or a mixture thereof.
  • Particular such embodiments are those wherein said at least one additional herbicide is 2,4-D. More particular such embodiments are those wherein the 2,4-D is in its free acid form.
  • At least one additional herbicide is a mixture of fluroxypyr and triclopyr. More particular such embodiments are those wherein each of the fluroxypyr and triclopyr in the mixture is in the form of an ester thereof.
  • esters of fluroxypyr include Ci-Cs-alkyl esters and C1-C4- alkoxy-C2-C4-alkyl esters, such as methyl esters, ethyl esters, isopropyl, butyl, hexyl, heptyl, isoheptyl, isooctyl, 2-ethylhexyl, methylheptyl (MHE; meptyl), butoxypropyl (butometyl), and butoxyethyl esters; and aryl esters such as benzyl; and non-limiting examples of esters of triclopyr include butoxy ethyl.
  • Specific aminopyralid-additional herbicide(s)-based formulations of the present invention comprise aminopyralid in the form of a free acid; a solvent combination comprising DMSO and an amide of the formula R-C(O)-N-((Ci-C4)alkyl)2, wherein R is (C?-Ci3)alkyl; a mixture of an alkyl benzene sulfonate salt-based surfactant (e.g., NINATE® 70B), at least one ethoxylated castor oil (e.g., a mixture of Surfom® R 400 and Surfom® R 200), and a dialkyl sulfosuccinate salt-based surfactant wherein said dialkyl sulfosuccinate salt-based surfactant comprises a di-(C?-Ci2)alkyl sulfosuccinate alkali metal salt such as sodium dioctyl sulfosuccinate (e.g.,
  • aminopyralid-additional herbicide(s)-based formulations of the present invention comprise aminopyralid in the form of a free acid; a solvent combination comprising DMSO and an amide of the formula R-C(O)-N-((Ci-C4)alkyl)2, wherein R is (C?-Ci3)alkyl; a mixture of an alkyl benzene sulfonate salt-based surfactant (e.g., NINATE® 70B), an ethoxylated castor oil (e.g., Surfom® R 400 and Surfom® R 200), a tri styrylphenol ethoxylate phosphate ester-based surfactant (e.g., Soprophor® 3D33), a trialkyl amine oxidebased surfactant (e.g., lauryl dimethylamine N-oxide such as Steprow® GP 103), and a dialkyl sulfosuccinate salt-based surfactant
  • compositions of the present invention comprise aminopyralid in the form of a free acid; a solvent combination comprising DMSO and A-(Ci-Cs)alkyl-2-pyrrolidone such as NBP; a mixture of an ethoxylated castor oil (e.g., Surfom® R 400 and Surfom® R 200) and a tri styrylphenol ethoxylate phosphate ester-based surfactant (e.g., Soprophor® 3D33); and a mixture of fluroxypyr and triclopyr, each in the form of an ester thereof. More specific such formulations are those wherein the ratio between the DMSO and said 7V-(Ci-Cs)alkyl-2- pyrrolidone is from 20
  • Still other specific aminopyralid-additional herbicide(s)-based formulations of the present invention comprise aminopyralid in the form of a free acid; a solvent combination comprising DMSO and a ketone of the formula R’-CO-R’, wherein R’ each independently is (Ci-Ce)alkyl, phenyl, or heteroaryl such as pyridyl, imidazolyl, and pyrimidinyl, or two of the R’s together with the carbon atom to which they are attached form a 5-7 membered ring (such as acetophenone); a mixture of an ethoxylated castor oil (e.g., a mixture of Surfom® R 400 and Surfom® R 200), a dialkyl sulfosuccinate salt-based surfactant wherein said dialkyl sulfosuccinate salt-based surfactant comprises a di-(C?-Ci2)alkyl sulfosucc
  • the present invention relates to various agricultural uses, e.g., pre- and/or post-emergence weed control, in which a formulation as defined in any one of the embodiments above is utilized.
  • a method of controlling weed also referred to herein as undesired vegetation, comprising applying to a locus an effective amount of a formulation as defined herein, in any one of the embodiments above.
  • locus refers not only to areas where the weed may already be developed, but also to areas where weeds have yet to emerge, and to areas under cultivation. Locus includes the crop and propagation material of the crop (all the generative parts of the crop such as seeds and vegetative plant material such as cuttings and tubers, which can be used for the multiplication of the plant). Examples of propagation material of the crop include seeds, tubers, spores, corms, bulbs, rhizomes, sprouts basal shoots, stolons, buds and other parts of plants, including seedlings and young plants, which could be transplanted after germination or after emergence from soil.
  • Locus also includes the area surrounding the crop and the growing media of the crop, such as soil and crop field.
  • the locus is a field of crop.
  • the term “crop” or “plant” as used herein refers to whole plants, plant organs (e.g., leaves, stems, twigs, roots, trunks, limbs, shoots, fruits, etc.), plant cells, or plant seeds.
  • crops are barley, wheat, oats, pasture, and rangeland. In particular such embodiments the crop is pasture.
  • Weeds that can be controlled by the method of the present invention are Bauhinia variegata, Bauhinia curvula, Lantana camara. Acacia fame si ana. Solanum lycocarpum, Eugenia dysenlerica. Doliocarpus denlalus. Sida glaziovii, Dioclea grandiflora. Solanum aculeatissimum, Sida acuta cv carpinifoha. Senna oblusifoHa. Hyptis suaveolens, Spermacoce latifolia, Sida rhombifoha. Vernonia polyanthes, Baccharis Irimera. Synedrellopsis grisebachii. Hyptis suaveolens, Senna oblusifoHa. Croton glandulosus. Sida cordifolia.
  • Acid equivalent - The amount of a pesticide expressed in terms of the parent acid or the amount that theoretically can be converted to the parent acid. Abbreviated as a.e.
  • formulations F-9, F-10, F-25, and F-26 were stable whereas formulations F-5 and F-6 did not form satisfying formulations.
  • formulations F-9, F-10, F-25, and F-26 contained, as a solvent combination, DMSO and an additional solvent, specifically M-V-di methyl decanamide (F-9, F-10), NBP (F-25), or acetophenone (F-26), as compared to F-5 which contained only soybean methyl ester as the solvent, and F-6 which contained the combination of DMSO and soybean methyl ester.
  • Formulations F-10, F-25, and F-26 showed also a good chemical stability under accelerated storage conditions, as depicted in Tables 3-5, respectively.

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

Abstract

La présente invention concerne une formulation herbicide comprenant : (i) de l'aminopyralide sous la forme d'un acide libre ; (ii) une combinaison de solvants comprenant du diméthylsulfoxyde (DMSO) et un solvant supplémentaire choisi parmi un solvant à base d'amide ; un solvant à base de cétone ; et un mélange de ceux-ci ; et (iii) au moins un tensioactif.
PCT/IL2025/050191 2024-02-29 2025-02-26 Compositions herbicides à base d'aminopyralide et leurs utilisations Pending WO2025181802A1 (fr)

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US63/559,228 2024-02-29

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007030885A1 (fr) * 2005-09-16 2007-03-22 Nufarm Australia Limited Concentre emulsifiable agrochimique
WO2010053784A2 (fr) * 2008-10-29 2010-05-14 Dow Agrosciences Llc Concentrés émulsifiables stables contenant un premier sel d'acide carboxylique herbicide et un second ester d'acide carboxylique herbicide
WO2011094388A2 (fr) 2010-01-29 2011-08-04 Dow Agrosciences Llc Composition herbicide synergique contenant de l'aminopyralide et de l'acide 2,4-dichlorophénoxyacétique
WO2014043151A1 (fr) * 2012-09-13 2014-03-20 Dow Agrosciences Llc Compositions herbicides comprenant de l'aminopyralide et du triclopyr
US20160050919A1 (en) * 2014-08-21 2016-02-25 Nufarm Americas, Inc. Acetyl-coa carboxylase inhibitor herbicide and auxin herbicide formulations
WO2019030614A1 (fr) * 2017-08-08 2019-02-14 Upl Ltd Compositions herbicides synergiques
WO2022194371A1 (fr) * 2021-03-17 2022-09-22 Globachem Nv Compositions herbicides de fluroxypyr

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007030885A1 (fr) * 2005-09-16 2007-03-22 Nufarm Australia Limited Concentre emulsifiable agrochimique
WO2010053784A2 (fr) * 2008-10-29 2010-05-14 Dow Agrosciences Llc Concentrés émulsifiables stables contenant un premier sel d'acide carboxylique herbicide et un second ester d'acide carboxylique herbicide
WO2011094388A2 (fr) 2010-01-29 2011-08-04 Dow Agrosciences Llc Composition herbicide synergique contenant de l'aminopyralide et de l'acide 2,4-dichlorophénoxyacétique
WO2014043151A1 (fr) * 2012-09-13 2014-03-20 Dow Agrosciences Llc Compositions herbicides comprenant de l'aminopyralide et du triclopyr
US20160050919A1 (en) * 2014-08-21 2016-02-25 Nufarm Americas, Inc. Acetyl-coa carboxylase inhibitor herbicide and auxin herbicide formulations
WO2019030614A1 (fr) * 2017-08-08 2019-02-14 Upl Ltd Compositions herbicides synergiques
WO2022194371A1 (fr) * 2021-03-17 2022-09-22 Globachem Nv Compositions herbicides de fluroxypyr

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TODD O.EFIGUEIREDO M.RMORRAN SSONI NPRESTON CKUBEŠ M.FNAPIER RGAINES T.A: "Synthetic auxin herbicides: finding the lock and key to weed resistance", PLANT SCIENCE, vol. 300, 2020, pages 110631, XP086310429, DOI: 10.1016/j.plantsci.2020.110631

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