WO2018082456A1 - Nouvelle forme de pénoxsulam, son procédé de préparation et son utilisation - Google Patents

Nouvelle forme de pénoxsulam, son procédé de préparation et son utilisation Download PDF

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Publication number
WO2018082456A1
WO2018082456A1 PCT/CN2017/107092 CN2017107092W WO2018082456A1 WO 2018082456 A1 WO2018082456 A1 WO 2018082456A1 CN 2017107092 W CN2017107092 W CN 2017107092W WO 2018082456 A1 WO2018082456 A1 WO 2018082456A1
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penoxsulam
crystalline modification
crystalline
solvent
exhibiting
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PCT/CN2017/107092
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English (en)
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James Timothy Bristow
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Jiangsu Rotam Chemistry Co., Ltd
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Priority to CN201780056601.6A priority Critical patent/CN109803970B/zh
Publication of WO2018082456A1 publication Critical patent/WO2018082456A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to a crystalline form of 3- (2, 2-difluoroethoxy) -N- (5, 8-dimethoxy [1, 2, 4] triazolo [1, 5-c] pyrimidin-2-yl) - ⁇ , ⁇ , ⁇ -trifluorotolu ene-2-sulfonamide (penoxsulam) , to its preparation processes and to its use in agrochemical preparations.
  • 3- (2, 2-difluoroethoxy) -N- (5, 8-dimethoxy [1, 2, 4] triazolo [1, 5-c] pyrimidin-2-yl) - ⁇ , ⁇ , ⁇ -trifluorotoluene-2-sulfonamide (penoxsulam) is a herbicide from the triazolo pyrimidine sulfonanilide family. It is a selective and highly active herbicide to control grasses, broadleaved weeds and sedges on rice. It is applied through the field or foliage using a suitable formulated product and absorbed through the root or foliage of the plants, respectively.
  • Penoxsulam has molecular formula of C 16 H 14 F 5 N 5 O 5 S. Its chemical structure is:
  • penoxsulam which is usually manufactured by the process described in U.S. Patent No. 5858924, which is incorporated herein by reference for all purposes, is present in an amorphous state. It has been found that amorphous penoxsulam is not suitable for being prepared as compositions or formulations as it is extremely susceptible to hydrolysis due to its unstable nature. It will undergo significant hydrolysis when dissolved or dispersed in water. Hydrolysis can even occur during storage, particularly where the compound is exposed to moisture. As a result, the stability of penoxsulam is of great concern for the commercially available formulations. Therefore, there is a need to provide a novel form of penoxsulam with increased stability in formulations.
  • aspects of the invention relate to a crystalline modification of 3- (2, 2-difluoroethoxy) -N- (5, 8-dimethoxy [1, 2, 4] triazolo [1, 5-c] pyrimidin-2-yl) - ⁇ , ⁇ , ⁇ -trifluorotolu ene-2-sulfonamide (penoxsulam) .
  • the present invention provides a novel crystalline form of 3- (2, 2-difluoroethoxy) -N- (5, 8-dimethoxy [1, 2, 4] triazolo [1, 5-c] pyrimidin-2-yl) - ⁇ , ⁇ , ⁇ -trifluorotoluene-2-sulfonamide (penoxsulam) , termed “crystalline modification I” , exhibiting at least 4 of the following reflexes, in any combination, as 2 ⁇ 0.2 degree in an X-ray powder diffractogram (X-RPD) recorded using Cu—K ⁇ radiation at 25°C:
  • X-RPD X-ray powder diffractogram
  • the crystalline modification according to the first aspect of the invention exhibits at least 4, 5, 6, 7, 8 or all of the reflexes, in any combination, from the following:
  • the present invention provides a crystalline modification I of penoxsulam, optionally according to the first aspect of the invention, exhibiting an infrared (IR) spectrum with characteristic functional group vibration peaks at wavenumbers (cm-1, ⁇ 0.2%) of 3360.72, 2925.19, 1637.23 and 1534.23 cm -1 .
  • IR infrared
  • the present invention provides a crystalline modification I of penoxsulam, optionally according to the first or second aspect of the invention, exhibiting a melting point of 227°C to 232°C.
  • the present invention provides a crystalline modification I of penoxsulam, optionally according to any one of the first to third aspects of the invention, exhibiting a differential scanning calorimetry (DSC) profile having an endothermic melting peak with onset at 228°C and peak maximum at 229°C, further optionally with a melting enthalpy of 80 J/g.
  • DSC differential scanning calorimetry
  • the present invention provides a crystalline modification I of penoxsulam, optionally according to any one of the first to fourth aspects of the invention, characterized by X-ray powder diffraction pattern as substantially shown in FIG. 2, and/or characterized by an IR spectrum as substantially shown in FIG. 1, and/or characterized by a DSC thermogram as substantially shown in FIG. 3.
  • the present invention provides a crystalline modification I of penoxsulam, optionally according to any one of the first to fifth aspects of the invention, obtainable by the process as substantially as described in Example 2 or 3.
  • the present invention provides a crystalline modification I of penoxsulam, optionally according to any one of the first to sixth aspects of the invention, obtainable by the process of the eighth aspect of the invention.
  • the present crystalline modification I of penoxsulam has a significant increase in its hydrolysis stability, which significantly reduces the hydrolysis problems encountered in current commercially available formulations.
  • the crystalline modification I of penoxsulam is easier to comminute or grind compared to amorphous penoxsulam prepared in accordance with the disclosure of US PAT. NO. 5,858,924.
  • the crystalline modification I has a lower tendency to hydrolysis after exposure to moisture compared to the amorphous state described in US PAT. NO. 5,858,924.
  • the present invention provides a process for preparing a crystalline modification I of penoxsulam comprising steps of:
  • the penoxsulam in step i) is amorphous penoxsulam.
  • Amorphous penoxsulam is manufactured and available on a commercial scale.
  • a particularly suitable method for preparing amorphous penoxsulam is described in US5858924.
  • the solvent is selected from the group consisting of halogenated hydrocarbons (for example, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene and trichlorobenzene) , ethers (for example, ethyl propyl ether, n-butyl ether, anisole, phenetole, cyclohexyl methyl ether, dimethyl ether, diethyl ether, dimethyl glycol, diphenyl ether, dipropyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, isopropyl ethyl ether, methyl tert-butyl ether, tetrahydrofuran, methyltetrahydrofuran, dioxane, dichlorodiethyl ether
  • halogenated hydrocarbons for
  • the solvent is selected from the group consisting of nitrobenzene, toluene, xylene, benzene, chlorobenzene, dichlorobenzene, ethyl benzene, trifluoro methyl benzene, mesitylene, ether, methyl ethyl ketone.
  • the solvent is selected from the group consisting of methyl ethyl ketone or xylene or a mixture thereof.
  • crystalline modification I of penoxsulam is prepared by dissolving amorphous penoxsulam in a solvent or a solvent mixture as a concentrated solution by heating from ambient temperature to a temperature at or below the reflux temperature of the solvent or the solvent mixture.
  • the concentrated solutions can be prepared at the reflux temperature of the solvents. The concentration of the solution depends on the solubility of penoxsulam in the corresponding solvent or solvent mixture.
  • the concentrated homogeneous solution thus prepared as in step (i) is then cooled to room temperature or to a temperature of about 0°C to 20°C to crystallize the desired crystalline form from the solvent.
  • the crystalline modification I of penoxsulam can also be crystallized out by concentrating the homogeneous solution by removing the solvent or solvent mixture to a certain volume with or without applying vacuum and cooling to below the reflux temperature of the solvent or the solvent mixture.
  • crystalline modification I of penoxsulam can also be effected by adding seed crystals of the desired crystalline form during crystallization into a solution prepared in step (i) , which can promote or accelerate the crystallization.
  • the seed crystal amount added to the concentrated solution is typically in the range of 0.001%to 10%by weight, optionally 0.001%to 2.5%by weight, further optionally 0.005 to 0.5%by weight based on the weight of penoxsulam used for the preparation of concentrated solution in step (i) .
  • the seed crystals are added to the concentrated solution at the temperature below the boiling point of the corresponding solvent or the solvent mixture.
  • the precipitated crystalline modification I of penoxsulam obtained from step (ii) is isolated by the usual solid component separating techniques from solutions, such as filtration, centrifugation or decantation. Then, the isolated solid will be washed with solvent one or more times.
  • the solvent employed in the washing stage consists of one or more components of the solvent or solvent mixture employed for the preparation of concentrated solution in step (i) , as described hereinbefore.
  • Methyl ethyl ketone and xylene are particularly suitable solvents for washing the recovered solid of penoxsulam. The washing is usually carried out using the corresponding solvent or solvent mixture between room temperature and 0°C, depending on the solubility of the crystal in order to avoid the loss of crystal as far as possible in the corresponding washing solvent.
  • crystalline modification I of penoxsulam is dissolved and recrystallized.
  • the washings and/or the solvent of crystallization in any of the methods may be concentrated to obtain solid penoxsulam which may be recycled.
  • the present invention provides a crystalline modification I of penoxsulam obtained according to the eighth aspect of the invention, having a crystalline penoxsulam content of at least 98%by weight.
  • the present invention provides a composition comprising the crystalline modification I of penoxsulam according to any one of the first to seventh and ninth aspects of the invention, and at least one auxiliary.
  • the present invention provides a use of the crystalline modification I of penoxsulam according to any one of the first to seventh and ninth aspects of the invention, or a composition according to the tenth aspect of the invention, for weed control.
  • the amount of the crystalline modification I of penoxsulam is less than 75%by weight of the composition, optionally less than 50%by weight of the composition, further optionally less than 30%by weight of the composition, still further optionally about 10%to 25%by weight of the composition.
  • amorphous penoxsulam as a herbicide is known in the art and is used on a commercial scale. It has been found that the crystalline modification I of penoxsulam is also active in controlling undesirable plant growth, such as weeds. As a result, the techniques of formulating and applying penoxsulam known in the art with respect to amorphous penoxsulam, for example as disclosed in the prior art documents discussed hereinbefore, can also be applied in an analogous manner to penoxsulam in the crystalline modification I of the invention.
  • the invention provides a herbicidal composition comprising penoxsulam in the crystalline modification I as defined hereinbefore.
  • the invention additionally provides processes for preparing compositions for controlling undesirable plants, such as weeds using the crystalline modification I of penoxsulam.
  • the invention also provides a method for controlling unwanted plant growth, comprising applying to the plant, plant part, or surroundings of the plant, a herbicidally effective amount of crystalline modification I of penoxsulam according to any one of the first to seventh and ninth aspects of the invention, or a composition according to the tenth aspect of the invention. Accordingly, this provides for controlling undesirable plants in plants, plant parts, and/or their surroundings, comprising applying to the foliage or fruit of the plant, plant part, or surroundings of the plant, a herbicidally effective amount of crystalline modification I of penoxsulam.
  • the composition is in the form of a suspension concentrate (SC) , oil-based suspension concentrate (OD) , water-soluble granule (SG) , dispersible concentrate (DC) , emulsifiable concentrate (EC) , emulsion seed dressing, suspension seed dressing, a granule (GR) , a microgranule (MG) , a suspoemulsion (SE) or water-dispersible granule (WG) .
  • Crystalline modification I of penoxsulam can be included into these customary formulations in a known manner using suitable auxiliaries, carriers and solvents and the like.
  • the composition is in the form of an oil-based suspension concentrate (OD) , a water-soluble granule (SG) , or a water-dispersible granule (WG) .
  • OD oil-based suspension concentrate
  • SG water-soluble granule
  • WG water-dispersible granule
  • the crystalline modification I of penoxsulam may be present in a concentration sufficient to achieve the required dosage when applied to plants or the loci thereof, desirably in a concentration of about 0.1%to 70%by weight of the total mixture.
  • the formulations are prepared, for example, by extending the crystalline modification I of penoxsulam with water, solvents and carriers, using, if appropriate, emulsifiers and/or dispersants, and/or other auxiliaries.
  • formulations are prepared by mixing the crystalline modification I of penoxsulam with customary additives, for example, one or more of liquid diluents, solid diluents, wetting agents, dispersants, thickening agents, antifreeze agents, antifoaming agents, biocides and any necessary adjuvants and other formulation ingredients.
  • customary additives for example, one or more of liquid diluents, solid diluents, wetting agents, dispersants, thickening agents, antifreeze agents, antifoaming agents, biocides and any necessary adjuvants and other formulation ingredients.
  • Liquid diluents include, but are not limited to, water, N, N-dimethylmamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, propylene carbonate, dibasic esters, paraffines, alkylbenzenes, alkyl naphthalenes, glycerine, triacetine, oils of olive, castor, linseed, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as hexyl acetate, heptyl acetate and octyl acetate, and alcohols such methanol, cyclohexanol, decanol, benzyl and tetrahydrofurfuryl alcohol, and mixtures
  • Solid diluents can be water-soluble or water-insoluble.
  • Water-soluble solid diluents include, but are not limited to, salts such as alkali metal phosphates (e.g., sodium dihydrogen phosphate) , alkaline earth phosphates, sulfates of sodium, potassium, magnesium and zinc, sodium and potassium chloride, sodium acetate, sodium carbonate and sodium benzoate, and sugars and sugar derivatives such as sorbitol, lactose, sucrose and mannitol.
  • alkali metal phosphates e.g., sodium dihydrogen phosphate
  • alkaline earth phosphates alkaline earth phosphates
  • sulfates of sodium, potassium, magnesium and zinc sodium and potassium chloride
  • sodium acetate sodium carbonate and sodium benzoate
  • sugars and sugar derivatives such as sorbitol, lactose, sucrose and mannitol.
  • Wetting agents include, but are not limited to, alkyl sulfosuccinates, laureates, alkyl sulfates, phosphate esters, acetylenic diols, ethoxyfluornated alcohols, ethoxylated silicones, alkyl phenol ethyoxylates, benzene sulfonates, alkyl-substituted benzene sulfonates, alkyl a-olefin sulfonates, naphthalene sulfonates, alkyl-substituted napthalene sulfonates, condensates of naphthalene sulfonates and alkyl-substituted naphthalene sulfonates with formaldehyde, and alcohol ethoxylates, and mixtures thereof. Alkyl naphthalene sulphonates, sodium salts are particularly useful for the composition of the
  • Dispersants include, but are not limited to, sodium, calcium and ammonium salts of ligninsulfonates (optionally polyethoxylated) ; sodium and ammonium salts of maleic anhydride copolymers; sodium salts of condensed phenolsulfonic acid; and naphthalene sulfonate-formaldehyde condensates.
  • compositions comprising up to 10%by weight of dispersant.
  • Ligninsulfonates such as sodium ligninsulfonates, naphthalene sulfonate-formaldehyde condensates such as naphthalenesulfonic acid, polymers with formaldehyde, and sodium salts are particularly useful for the composition of the invention.
  • Thickening agents include, but are not limited to, guar gum, pectin, casein, carrageenan, xanthan gum, silica, alginates, methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, and carboxymethylcellulose.
  • Synthetic thickening agents include derivatives of the former categories, and also polyvinyl alcohols, polyacrylamides, polyvinylpyrrolidones, various polyethers, their copolymers as well as polyacrylic acids and their salts. Silica is particularly useful for the composition of the invention.
  • Suitable antifreeze agents are liquid polyols, for example ethylene glycol, propylene glycol or glycerol.
  • the amount of antifreeze agents is generally from about 1%to about 20%by weight, in particular from about 5 to about 10%by weight, based on the total weight of the composition.
  • Antifoaming agents include all substances which can normally be used for this purpose in agrochemical compositions. Suitable anti-foam agents are known in the art and are available commercially. Particularly preferred antifoam agents are mixtures of polydimethylsiloxanes and perfluroalkylphosphonic acids, such as the silicone antifoaming agents available from GE or Compton.
  • Biocide may also be added to the composition according to the invention.
  • Suitable Biocides are those based on isothiazolones, for example from ICI or RS from Thor Chemie or MK from Rohm &Haas.
  • the amount of biocides is typically from 0.05%to 0.5%by weight, based on the total weight of the composition.
  • formulation ingredients can also be used in the present invention such as dyes, drying agents, and the like. These ingredients are known to one skilled in the art.
  • the crystalline modification I of penoxsulam can be present in formulations and in its use forms, prepared from these formulations, and as a mixture with other active compounds (such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers and semiochemicals) or with agents for improving plant properties.
  • active compounds such as insecticides, attractants, sterilizing agents, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers and semiochemicals
  • Preferred mixing partners of the crystalline modification I of penoxsulam include cyhalofop-butyl, substituted triazolopyrimidinesulfonamide compounds, such as diclosulam, cloransulam-methyl, flumetsulam.
  • herbicides such as acifluorfen, bentazon, chlorimuron, clomazone, lactofen, carfentrazone-methyl, fumiclorac, fluometuron, fomesafen, imazaquin, imazethapyr, linuron, metribuzin, fluazifop, haloxyfop, glyphosate, glufosinate, 2, 4-D, acetochlor, metolachlor, sethoxydim, nicosulfuron, clopyralid, fluroxypyr, metsulfuron-methyl, amidosulfuron, tribenuron-methyl, thifensulfuron-methyl, flupyrsulfuron-methyl-sodium mesosulfuron-methyl, iodosulfuron-methyl-sodium, rimsulfuron, halosulfuron-methyl, trifloxysulfuron-sodium and chlorsulfuron can also be employed.
  • plants and plant parts can be treated in accordance with the invention.
  • plants are to be understood as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants) .
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods, by biotechnological and genetic engineering methods, or by combinations of these methods, including the transgenic plants and the plant cultivars which can or cannot be protected by plant breeders'rights.
  • Plant parts are to be understood as meaning all parts and organs of plants above and below the ground, such as shoot, leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes.
  • Harvested materials, and vegetative and generative propagation materials for example, cutting, tubers, meristem tissue, rhizomes, offsets, seeds, single and multiple plant cells and any other plant tissues, are also included.
  • the benefits of the invention are seen most when the herbicidal composition is applied to kill weeds in growing crops of useful plants: such as sugarcane, corn, cereals, rice, maize, sorghum, cotton, canola, turf, barley, potato, sweet potato, sunflower, rye, oats, wheat, soybean, soya, sugar beet, tobacco, safflower, tomato, alfalfa, pineapple, cucurbits cassava and pastures.
  • crops of useful plants such as sugarcane, corn, cereals, rice, maize, sorghum, cotton, canola, turf, barley, potato, sweet potato, sunflower, rye, oats, wheat, soybean, soya, sugar beet, tobacco, safflower, tomato, alfalfa, pineapple, cucurbits cassava and pastures.
  • rice and cereals are particularly suitable for treatment.
  • references to properties are –unless stated otherwise –to properties measured under ambient conditions, i.e. at atmospheric pressure and at a temperature of about 20°C.
  • the term “about, ” when used in connection with a numerical amount or range, means somewhat more or somewhat less than the stated numerical amount or range, to a deviation of ⁇ 10%of the stated numerical amount or endpoint of the range.
  • crystalline refers to a solid state form wherein molecules are arranged to form a crystal lattice comprising distinguishable unit cells.
  • crystalline material may, for example, be identified by yielding diffraction peaks when subjected to X-ray radiation and/or exhibiting an endothermic melting peak profile with a characteristic sharp peak under differential scanning calorimetry (DSC) .
  • DSC differential scanning calorimetry
  • “Surrounding” refers to the place on which the plants are growing, the place on which the plant propagation materials of the plants are sown or the place on which the plant propagation materials of the plants will be sown.
  • compositions or formulations of the inventions Treatment of the plants and plant parts with the compositions or formulations of the inventions is carried out directly or by allowing the compositions or formulations to act on their surroundings, habitat or storage space by the customary treatment methods.
  • customary treatment methods include dipping, spraying, vaporizing, fogging, broadcasting, painting on in the case of propagation material, and applying one or more coats particularly in the case of seed.
  • Precipitation refers to the sedimentation of a solid material (a precipitate) , including the sedimentation of a crystalline material, from a liquid solution in which the solid material is present in amounts greater than its solubility in the amount of liquid solution.
  • FIG. 1 is a an infrared (IR) spectrograph of crystalline modification I of penoxsulam
  • FIG. 2 is a X-ray powder diffractogram of crystalline modification I of penoxsulam
  • FIG. 3 is a Differential Scanning Calorimetry (DSC) thermogram of crystal modification I of penoxsulam
  • FIG. 4 is a X-ray powder diffractogram of amorphous penoxsulam.
  • the IR spectrum was measured with the resolution of 4 cm -1 and with the number of scans of 16 for the crystallized samples.
  • the crystalline modification I of penoxsulam can be identified by its characteristic functional group vibration peaks at wavenumbers (cm -1 , ⁇ 0.2%) of 3360.72, 2925.19, 1637.23 and 1534.23 as shown in FIG. 1.
  • Example 1 Preparation of amorphous penoxsulam in accordance with the disclosure of U.S. Pat. No. 5,858,924 with necessary modification in Example 20
  • the X-ray powder diffraction pattern of the resulting penoxsulam product has no significant signals, which indicates that the penoxsulam product prepared in accordance with the disclosure of U.S. Pat. No. 5,858,924 is amorphous.
  • the obtained crystals were analyzed by DSC, IR spectrometry and X-ray powder diffraction and found to crystalline modification I of penoxsulam as shown in FIG. 1, FIG. 2 and FIG. 3, respectively.
  • the DSC thermogram of penoxsulam exhibited an endothermic melting peak with onset at 227.5°C and peak maximum at 229.2°C, further optionally with a melting enthalpy of 79.66 J/g as shown in FIG. 3.
  • the IR spectrum of the crystalline modification I of penoxsulam exhibited the functional group characteristic vibrations peaks at wavenumbers of one or more of 3360.72, 2925.19, 1637.23 and 1534.23 cm -1 as shown in FIG. 1.
  • amorphous penoxsulam sample prepared in example 1 was taken in a 3-neck round bottom flask along with 30mL of xylene and the resulting slurry was heated to 83°C to get a homogeneous solution.
  • the insoluble particles, if any, were filtered and the solution was slowly cooled to 20 ⁇ 25°C. Upon cooling, fine crystals were formed and the resulting heterogeneous mixture was stirred at 20°C for 2h. Then, the slurry was filtered, washed with 3mL of xylene at 20°C. The filtered crystals were dried under vacuum at 45°C.
  • the crystalline product thus obtained were having a purity of >98%and the the recovered product as crystal was found to be not less than 80%yield.
  • the obtained crystals were characterized as being the crystalline modification I of penoxsulam using IR spectrometry, X-ray powder diffraction and DSC as described in Example 2.
  • Penoxsulam content was determined by assaying the compositions with high-pressure liquid chromatography (HPLC) using reverse phase columns and eluants.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

L'invention concerne une nouvelle forme cristalline de pénoxsulam de formule (I), le procédé de préparation du cristal, les analyses du cristal par divers procédés analytiques, et l'utilisation du cristal pour préparer une formulation agrochimique stable. L'invention concerne également l'utilisation de différents solvants selon les conditions de préparation de ladite forme cristalline.
PCT/CN2017/107092 2016-11-07 2017-10-20 Nouvelle forme de pénoxsulam, son procédé de préparation et son utilisation WO2018082456A1 (fr)

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