WO2020133014A1 - Forme cristalline c d'un sel de cypyrafluone monoisopropylamine, son procédé de préparation et son utilisation - Google Patents

Forme cristalline c d'un sel de cypyrafluone monoisopropylamine, son procédé de préparation et son utilisation Download PDF

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Publication number
WO2020133014A1
WO2020133014A1 PCT/CN2018/124122 CN2018124122W WO2020133014A1 WO 2020133014 A1 WO2020133014 A1 WO 2020133014A1 CN 2018124122 W CN2018124122 W CN 2018124122W WO 2020133014 A1 WO2020133014 A1 WO 2020133014A1
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WIPO (PCT)
Prior art keywords
ciprofloxacin
crystalline form
isopropylamine salt
weeds
methyl
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PCT/CN2018/124122
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English (en)
Chinese (zh)
Inventor
连磊
赵德
彭学岗
金涛
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青岛清原化合物有限公司
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Publication of WO2020133014A1 publication Critical patent/WO2020133014A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the invention belongs to the technical field of herbicide crystallization technology, and particularly relates to a crystalline form of ciprofloxacin-isopropylamine salt, and a preparation method and application thereof.
  • Ciprofloxacin (structural formula: ) Is a newly developed HPPD inhibitor herbicide for post-emergence stem and leaf treatment of wheat fields, which has excellent biological activity and can effectively control a variety of malignant grass weeds in wheat fields.
  • the compound patent has been authorized, authorization announcement number: CN 105218449 B.
  • Polymorphism refers to the phenomenon in which solid substances form solid states with different physical and chemical properties in two or more different spatial arrangements. Different crystal forms have different colors, melting points, dissolution, dissolution properties, chemical stability, reactivity, mechanical stability, etc. These physical and chemical properties or processability sometimes directly affect the safety and effective performance of drugs. Therefore, crystal form research and control has become an important research content in the process of drug development.
  • the present invention provides a new herbicide ciprofloxacin-isopropylamine salt C crystal form and its preparation method and use.
  • the crystal form has good physical and chemical stability, high solubility and high biological activity, and can be used for controlling common weeds in crop fields.
  • the corresponding I/I 0 is 3.5, 53.5, 8.9, 80.6, 12.7, 2.8, 100.0, 46.5, 19.3, 3.9, 12.8, 11.6, 18.9, 51.8, 10.3, 5.1, 12.9, 5.7, 26.1, 23.5 , 25.8, 41.3, 12.9, 8.5, 9.4, 3.6, 14.3, 9.7, 4.7, 4.5, 3.2, 5.7, 27.9, 3.7, 5.0, 1.4, 2.7, 5.3, 2.1, 3.5, 3.0, 2.0.
  • its X-ray powder diffraction pattern is substantially as shown in FIG. 1.
  • the preparation method of the crystalline form C of ciprofloxacin-isopropylamine salt includes the following steps: dissolve the ciprofloxacin-isopropylamine salt in methanol, stir until completely dissolved, and then add 1-10 times the volume of Methyl tert-butyl ether causes a large amount of solid crystals to precipitate out of the solution, and the resulting solid crystals are dried to obtain crystalline form C of flupiroxone-isopropylamine salt.
  • a herbicidal compound composition comprising (i) the crystalline form of cyclofluxonone isopropylamine salt; preferably, it also includes (ii) one or more other active ingredients and/or safeners; Preferably, (iii) agrochemically acceptable formulation aids are also included.
  • the auxiliary agent is selected from one or more of solvents, solid diluents, emulsifiers, wetting agents, dispersants, antifreeze agents, defoamers and thickeners.
  • Selected solvents include but are not limited to polar solvents: water, N,N-dimethylamide, dimethyl sulfoxide, N-alkylpyrrolidone, methanol, ethanol, ethylene glycol, isopropanol, ethylene glycol Butyl ether, propylene glycol methyl ether, etc.; aromatic hydrocarbon solvent oil series: toluene, xylene, No. 100 solvent oil, No. 150 solvent oil, No. 180 solvent oil, No.
  • the selected solid diluent may be water-soluble or water-insoluble.
  • Water-soluble solid diluents include, but are not limited to: salts, such as alkali metal phosphates (sodium dihydrogen phosphate), alkaline earth metal phosphates, sodium, potassium, magnesium and zinc sulfates, sodium chloride and potassium chloride, sodium acetate , Sodium carbonate and sodium benzoate, as well as sugar and sugar derivatives, such as sorbitol, lactose, sucrose and mannitol, corn starch, etc.
  • non-water soluble solid diluents include, but are not limited to: clay, calcium carbonate, diatomaceous earth, white carbon, calcium silicate, bentonite, magnesium aluminum silicate, kaolin and the like.
  • Wetting agents include, but are not limited to: alkyl sulfosuccinates, laurates, alkyl sulfates, phosphates, ethoxylated fluorinated alcohols, ethoxylated silicones, alkylphenol ethoxylates , Benzene sulfonate, alkyl substituted benzene sulfonate, alkyl ⁇ -olefin sulfonate, naphthalene sulfonate, alkyl substituted naphthalene sulfonate alkali metal salt, naphthalene sulfonate alkali metal salt and alkyl substitution Condensate of naphthalene sulfonate and formaldehyde, alcohol ethoxylate.
  • Dispersants include, but are not limited to: sodium, calcium and ammonium salts of lignin sulfonic acid; sodium and ammonium salts of maleic anhydride copolymer; sodium salts of condensed phenolsulfonic acid; naphthalenesulfonate-formaldehyde condensate ; Phosphate ester dispersant, polycarboxylate dispersant, etc.
  • Thickeners include, but are not limited to: guar gum, pectin, xanthan gum, alginate, methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, magnesium aluminum silicate, and the like.
  • Synthetic thickeners include derivatives of the foregoing types, and also include polyvinyl alcohol, polyacrylamide, polyvinylpyrrolidone, various polyethers and their copolymers, and polyacrylic acid and their salts.
  • formulation ingredients such as dyes, defoamers, desiccants, etc. can be used in the present invention. These ingredients are well known to those skilled in the art.
  • Suitable active ingredients that can be mixed with the crystalline form C of ciprofloxone-isopropylamine salt of the present invention are, for example, "World Pesticide New Variety Technology Encyclopedia", China Agricultural Science and Technology Press, 2010.9 and the documents cited here Known substances.
  • acetochlor butachlor, alachlor Amine, propachlor, metolachlor, mesochlor, alachlor, alachlor, alachlor, naproxen, R-levonapropion, dipropanil, benzene Alafenamide, difenacetamide, flufenacetamide, chlorfenapyr, flufenacetamide, bromobutyramide, dimethoxamide, high-efficiency dimethoxamide, ethoxybenzamide Amine, flufenazone, alafenamide, metazachlor, clomazone, high-efficiency dicofol, high-efficiency propylpropanil, dipropoxyfen, dimethoprim, butachlor, cyprofen Glufosinate, fluoxanilam, h
  • the other active ingredients include, but are not limited to: pyrachlor (CAS No.: 83164-33-4), isoxaflutole (CAS No.: 141112-29-0), cypromethrin (CAS No.: 105512-06-9), oxazolin (CAS No.: 243973-20-8), isoproturon (CAS No.: 34123-59-6), chlormeron (CAS No.: 15545-48-9 ), octanoyl bromoxynil (CAS number: 1689-99-2), azoxystrobin (CAS number: 21087-64-9), dapyridine (CAS number: 55512-33-9), azaprofen (CAS number: 129909-90-6), 2 methyl 4 chlorine (CAS number: 94-74-6), chlorofluoropyroxyacetic acid (CAS number: 69377-81-7), fluorochloropyridine ester (CAS number: 943831-98-9), dicamba (CAS number: 1918-00
  • salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group.
  • 2M 4 Chlorine derivatives include but are not limited to: 2M 4 Chlorine sodium salt, potassium salt, dimethyl ammonium salt, isopropylamine salt, etc., as well as 2M 4 Chlorine methyl ester, ethyl ester, isooctyl ester, ethyl sulfide Ester etc.
  • the salt of the compound is preferably in the form of a respective alkali metal salt, alkaline earth metal salt or ammonium salt, preferably in the form of a respective alkali metal salt, more preferably in the form of a respective sodium or potassium salt, Most preferred is the form of the respective sodium salt.
  • the total mass percentage of active ingredients in the composition accounts for 1-95% of the total.
  • the safener is preferably bisoxazolic acid (CAS: 163520-33-0), cyprosulfamide (CAS: 221667-31-8), pyrazolinate (CAS: 135590-91-9), detoxified quinoline (CAS : 99607-70-2), gibberellic acid (CAS: 7-06-5), furilazole (CAS: 121776-33-8), one or more of metcamifen (CAS: 129531-12-0).
  • the dosage form of the composition is water suspension (SC), dispersible oil suspension (OD), emulsifiable concentrate (EC), microemulsion (ME), granule (GR), suspension emulsion (SE) or water dispersible granule (WDG).
  • SC water suspension
  • OD dispersible oil suspension
  • EC emulsifiable concentrate
  • ME microemulsion
  • GR granule
  • SE suspension emulsion
  • WDG water dispersible granule
  • the invention also provides a method for controlling weeds in crops, which comprises using a herbicidally effective amount of the crystalline form C of ciprofloxacin-isopropylamine salt or the herbicidal compound composition on crops or Weed area.
  • the present invention also provides the use of the ciprofloxone-isopropylamine salt crystal form C or the herbicidal compound composition in controlling weeds; preferably, it is used to control impurities in useful crops Grass, the useful crops are genetically modified crops or crops processed by genome editing technology.
  • the crop is wheat
  • the weeds are gramineous weeds, such as maidenhair, Japanese maidenhair, etc.
  • the ciprofloxone-isopropylamine salt C crystal form of the present invention has been tested and has good physical and chemical stability, good water solubility, and the solubility in water is increased more than ten times compared to ciprofloxacin, compared to ciprofloxacin
  • the sodium salt of ketone increases nearly six times, and the crystalline form C or the compound composition with other active ingredients has a good control effect on wheat field grasses weeds, and the effect is significantly better than ciprofloxacin and its Sodium salt.
  • FIG. 1 is an XRPD pattern of the crystalline form C of flufenazone-isopropylamine salt of Example 2 in the present invention.
  • Instrument model Bruker D8 advance, target: Cu K ⁇ (40kV, 40mA), sample-to-detector distance: 30cm, scanning range: 3 0 -45 0 (2 ⁇ value), scanning step size: 0.05s.
  • Example 2 1 kg of cyclofluxonone obtained in Example 1 was reacted with 0.27 kg of 50% aqueous solution of monoisopropylamine to obtain a large amount of solid crystals. The solid was filtered and dried to obtain powder of cyclofluxonone-isopropylamine salt.
  • the three powders of ciprofloxacin and its sodium salt obtained in Example 1 and the crystalline form of ciprofloxacin-isopropylamine obtained in Example 2 were measured by HPLC.
  • the content of ciprofloxacin was 97.2%.
  • the content of fluroxypyr sodium salt is 98.0%, and the content of cyclofipronone-isopropylamine C crystal form is 98.0%.
  • the three original drug powders are placed at 25 °C, 40 °C, 55 °C and 70 Place in the oven at °C for 2 months to conduct the heat storage experiment, and then test the purity.
  • Ciprofloxacin Ciprofloxan sodium salt
  • Ciprofloxacin-isopropylamine salt form C 25°C 97.2% 98.0% 98.0% 40°C 96.6% 97.8% 97.9% 55°C 96.1% 97.3% 97.7% 70°C 95.5% 96.5% 97.3%
  • Example 2 The two powders of ciprofloxanone and its sodium salt obtained in Example 1 and the crystalline form of ciprofloxone-isopropylamine salt obtained in Example 2 were dissolved in pure water and shaken at 25°C for 24h , To make it fully dissolved, then centrifuged and filtered, the filtrate was passed through a 0.22 ⁇ m filter membrane, and the solubility in water was determined by HPLC. The results are shown in Table 2 below:
  • the ciprofloxanone and its sodium salt obtained in Example 1 and the crystalline form of ciprofloxone-isopropylamine salt C obtained in Example 2 were processed into the following formulations according to the same formula.
  • the specific formula is as follows, which is effective Component A represents the crystalline form of ciprofloxacin, ciprofloxacin sodium salt and ciprofloxacin-isopropylamine salt.

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

Abstract

L'invention concerne une forme cristalline C d'un sel de cypyrafluone monoisopropylamine, son procédé de préparation et son utilisation. Le motif de diffraction de rayons X sur poudre de la forme cristalline C du sel de cypyrafluone monoisopropylamine présente des pics caractéristiques à des angles de diffraction 2θ de 6,9°, 7,4°, 8,3°, 10,2°, 11,3°, 12,5°, 14,0°, 15,1°, 16,3°, 17,0°, 18,0°, 18,7°, 19,2°, 20,0°, 20,6°, 21,2°, 21,7°, 22,3°, 23,0°, 24,8°, 25,9°, 26,2°, 27,5°, 28,1°, 28,4°, 29,4°, 30,3°, 30,8°, 31,3°, 31,8°, 33,4°, 34,0°, 34,7°, 35,8°, 37,0°, 37,7°, 38,2°, 38,8°, 40,1°, 40,7°, 42,6° et 44,0°, la plage d'erreur de 2θ étant de ± 0,2°. La forme cristalline C du sel de cypyrafluone monoisopropylamine présente une bonne stabilité physico-chimique, une grande solubilité et une activité biologique élevée, et peut être utilisée pour prévenir et éliminer des mauvaises herbes.
PCT/CN2018/124122 2018-12-25 2018-12-27 Forme cristalline c d'un sel de cypyrafluone monoisopropylamine, son procédé de préparation et son utilisation WO2020133014A1 (fr)

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CN201811592545.0A CN111362906B (zh) 2018-12-25 2018-12-25 环吡氟草酮一异丙胺盐c晶型及其制备方法和用途

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CN109819988A (zh) * 2019-01-28 2019-05-31 南京农业大学 一种环吡氟草酮与绿麦隆治理抗性日本看麦娘组合物及其应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046530A1 (fr) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
CN105218449A (zh) * 2015-11-06 2016-01-06 青岛清原化合物有限公司 吡唑酮类化合物或其盐、制备方法、除草剂组合物及用途
CN106070226A (zh) * 2016-06-07 2016-11-09 泰安市农业科学研究院 一种环吡氟草酮组合物及其用途
CN107286095A (zh) * 2017-07-13 2017-10-24 青岛清原化合物有限公司 双唑草酮d晶型及其制备方法和用途
CN107629035A (zh) * 2017-10-24 2018-01-26 青岛清原化合物有限公司 一种吡唑酮类化合物或其盐、除草剂组合物及用途

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UA111193C2 (uk) * 2011-03-25 2016-04-11 Баєр Інтеллекчуел Проперті Гмбх Застосування n-(тетразол-4-іл)- або n-(триазол-3-іл)арилкарбоксамідів або їх солей для контролю небажаних рослин на площах трансгенних культур, що толерантні до гербіцидів, що є інгібіторами hppd
CN106472517B (zh) * 2016-09-30 2018-11-02 江苏清原农冠杂草防治有限公司 增效除草组合物及其应用
CN107810963A (zh) * 2017-11-09 2018-03-20 青岛清原化合物有限公司 一种含环吡氟草酮的除草组合物及其应用
CN109042675B (zh) * 2018-07-21 2021-05-28 青岛清原化合物有限公司 包含hppd抑制剂类除草剂的三元除草组合物及其应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997046530A1 (fr) * 1996-06-06 1997-12-11 E.I. Du Pont De Nemours And Company Pyridinylcetones et pyrazolylphenylcetones herbicides
CN105218449A (zh) * 2015-11-06 2016-01-06 青岛清原化合物有限公司 吡唑酮类化合物或其盐、制备方法、除草剂组合物及用途
CN106070226A (zh) * 2016-06-07 2016-11-09 泰安市农业科学研究院 一种环吡氟草酮组合物及其用途
CN107286095A (zh) * 2017-07-13 2017-10-24 青岛清原化合物有限公司 双唑草酮d晶型及其制备方法和用途
CN107629035A (zh) * 2017-10-24 2018-01-26 青岛清原化合物有限公司 一种吡唑酮类化合物或其盐、除草剂组合物及用途

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