WO2021005545A1 - A process for obtaining indoxacarb crystals with specific purity and enantiomeric ratio - Google Patents
A process for obtaining indoxacarb crystals with specific purity and enantiomeric ratio Download PDFInfo
- Publication number
- WO2021005545A1 WO2021005545A1 PCT/IB2020/056457 IB2020056457W WO2021005545A1 WO 2021005545 A1 WO2021005545 A1 WO 2021005545A1 IB 2020056457 W IB2020056457 W IB 2020056457W WO 2021005545 A1 WO2021005545 A1 WO 2021005545A1
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- WO
- WIPO (PCT)
- Prior art keywords
- indoxacarb
- crystals
- isomer
- range
- enantiomeric
- Prior art date
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- 0 COC(*(CCC(N(COC1(C2)C(OC)=O)N=C1c(cc1)c2cc1Cl)=O)c(cc1)ccc1OC(F)(F)F)=O Chemical compound COC(*(CCC(N(COC1(C2)C(OC)=O)N=C1c(cc1)c2cc1Cl)=O)c(cc1)ccc1OC(F)(F)F)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
Definitions
- the present disclosure relates to a process for obtaining Indoxacarb crystals with specific purity and specific enantiomeric ratio.
- Equilibration refers to a process of allowing an enantiomeric solution to attain equilibrium, for obtaining a specific enantiomeric ratio.
- Crude Indoxacarb refers to Indoxacarb obtained from a manufacturing unit, comprising optically active isomer of Indoxacarb (S-isomer) and optically inactive isomer of Indoxacarb (R-isomer) along with impurities.
- Crude Indoxacarb is either amorphous or crystalline in nature.
- the impurities are inert in nature comprising compounds such as oxadiazine precursor, oil, solvent and the like.
- the amount of impurities present in crude Indoxacarb is in the range of 10 wt. % to 15 wt.%.
- Indoxacarb is an oxadiazine compound with pesticidal activity, especially effective against lepidopteran larvae.
- Crude Indoxacarb can be either in amorphous form or in crystalline form.
- the crystalline form of Indoxacarb exhibits improved properties and stability in formulations as compared to the amorphous form, wherein the latter has a greater tendency to aggregate.
- the process of obtaining a crystalline form with high purity is tedious and expensive.
- the insecticidal activity of Indoxacarb is mainly attributed to the (+)-S-isomer whereas the R-isomer is inactive.
- the purification process for improving the purity of the crystalline form may lead to deterioration in the amount of the S-isomer.
- Another object of the present disclosure is to provide Indoxacarb crystals having specific purity and specific enantiomeric ratio.
- Still another object of the present disclosure is to provide an efficient process for obtaining Indoxacarb crystals with specific purity without any deterioration in the amount of the S- isomer.
- the present disclosure provides a process for obtaining an enantiomeric mixture of Indoxacarb crystals having purity in the range of 95% to 99.5%.
- the process comprises mixing crude Indoxacarb with a solvent to obtain a slurry, wherein the crude Indoxacarb comprises impurities in an amount in the range of 10 wt.% to 15 wt.%.
- the slurry is heated to a temperature in the range of 74 °C to 85 °C to obtain a heated slurry.
- the heated slurry is cooled to a temperature in the range of 55 °C to 70 °C to allow partial crystallization and obtain a warm slurry comprising crystals of racemic Indoxacarb.
- At least one portion of the warm slurry is filtered at a temperature in the range of 55 °C to 70 °C to isolate a mass comprising the crystals of racemic Indoxacarb and obtain a filtrate.
- the filtrate is mixed with the remaining portion of the warm slurry to obtain a first mixture.
- the first mixture is cooled to a temperature in the range of 10 °C to 25 °C to initiate crystallization followed by equilibrating under stirring for a time period in the range of 3 hours to 8 hours to allow complete crystallization to obtain a second mixture containing enantiomeric crystals of Indoxacarb comprising R-isomer and S-isomer of Indoxacarb.
- the second mixture is filtered to separate the enantiomeric crystals of Indoxacarb.
- the crystals are washed and dried to obtain an enantiomeric mixture of Indoxacarb crystals having purity in the range of 95% to 99.5%; wherein said enantiomeric mixture of Indoxacarb comprises crystals of R-isomer and S-isomer, wherein the S-isomer crystals are present in an amount in the range of 75% to 90% of said enantiomeric mixture.
- Crude Indoxacarb comprises an enantiomeric mixture containing crystals of R-isomer and S- isomer, wherein the crystals of S-isomer are present in an amount of at least 70% of the enantiomeric mixture.
- the present disclosure provides an enantiomeric mixture of Indoxacarb crystals having purity in the range of 95% to 99.5%.
- the enantiomeric mixture comprise crystals of R-isomer and S-isomer of Indoxacarb.
- the S-isomer crystals are present in an amount in the range of 75 % to 90% of the enantiomeric mixture.
- FIG 1 illustrates Differential scanning calorimetry (DSC) graph of sample 1A (racemic mixture), in accordance with the process of the present disclosure
- FIG. 2 illustrates Differential scanning calorimetry (DSC) graph of sample 2A, in accordance with the process of the present disclosure
- FIG. 3 illustrates X-Ray Diffraction (XRD) data of sample 1A (racemic mixture), in accordance with the process of the present disclosure
- Figure 4 illustrates X-Ray Diffraction (XRD) data of sample 2A (mixture of R and S isomers of Indoxacarb), in accordance with the process of the present disclosure.
- Embodiments are provided so as to thoroughly and fully convey the scope of the present disclosure to the person skilled in the art. Numerous details, are set forth, relating to specific components, and methods, to provide a complete understanding of embodiments of the present disclosure. It will be apparent to the person skilled in the art that the details provided in the embodiments should not be construed to limit the scope of the present disclosure. In some embodiments, well-known processes, well-known apparatus structures, and well-known techniques are not described in detail.
- first, second, third, etc. should not be construed to limit the scope of the present disclosure as the aforementioned terms may be only used to distinguish one element, component, region, layer or section from another component, region, layer or section. Terms such as first, second, third etc., when used herein do not imply a specific sequence or order unless clearly suggested by the present disclosure.
- Indoxacarb (I) is an important pesticidal compound, having oxadiazine as the structural unit and a single chiral center. Indoxacarb shows improved properties in its crystalline form than in the amorphous form.
- the insecticidal activity of Indoxacarb is mainly attributed to the (+)-S-isomer whereas the R-isomer is inactive.
- Conventional processes of obtaining crystalline Indoxacarb lead to a mixture of R-isomer and S-isomer, and further purification would lead to the deterioration in the amount of the S-isomer, thus reducing the overall activity, as the S-isomer is the active component.
- the present disclosure provides a simple and effective process for preparing Indoxacarb crystals having a specific purity and a specific enantiomeric ratio.
- the process enhances the purity of Indoxacarb, with the same or relatively higher amount of S-isomer than that in the crude Indoxacarb.
- the present disclosure provides a process for obtaining an enantiomeric mixture of Indoxacarb crystals having purity in the range of 95% to 99.5%. The process is described in detail herein below.
- Crude Indoxacarb is mixed with a solvent to obtain a slurry.
- the crude Indoxacarb comprises impurities in an amount in the range of 10 wt.% to 15 wt.%.
- the crude Indoxacarb has purity in the range of 70% to 90%.
- Crude Indoxacarb obtained from a manufacturing unit, comprises optically active isomer of Indoxacarb (S-isomer) and optically inactive isomer of Indoxacarb (R-isomer) along with impurities.
- the impurities are inert in nature comprising compounds such as oxadiazine precursor, oil, solvent.
- the amount of impurities in crude Indoxacarb are in an amount in the range of 10 wt. % to 15 wt.%.
- Crude Indoxacarb is either amorphous or crystalline in nature.
- Crude Indoxacarb comprises an enantiomeric mixture containing crystals of R-isomer and S- isomer, wherein the crystals of S-isomer are present in an amount of at least 70% of the enantiomeric mixture. In an embodiment, the crystals of S-isomer in crude Indoxacarb are present in an amount of 75% of the enantiomeric mixture. In an embodiment, the crude Indoxacarb is obtained in an amorphous lump form.
- the crude Indoxacarb has purity of 86%. In another embodiment, the crude Indoxacarb has purity of 88%.
- the crude Indoxacarb has impurity of 13 wt.%.
- the solvent is selected from aliphatic alcohols with Ci to Cio carbon atoms and cyclic alcohols.
- the solvent is selected from the group consisting of methanol, ethanol, 2-propanol, 1 -butanol and cyclohexanol.
- the solvent is 2-propanol.
- the weight-volume ratio of crude Indoxacarb and the solvent in the mixing step is in the range of 1:0.8 to 1:1.5. In an embodiment, the weight-volume ratio of crude Indoxacarb and the solvent is 1:1.
- the weight- volume ratio value lesser than 1:0.8 would lead to insufficient solubility whereas a ratio greater than 1:1.5 would lead to the use of excess solvent which not only leads to wastage but also affects the recrystallization of R-isomers and S -isomers during equilibration, resulting in comparatively lesser recovery.
- the impurities are mainly inert impurities that get dissolved by the solvent at room temperature.
- the slurry is heated to a temperature in the range of 74 °C to 85 °C to obtain a heated slurry.
- the slurry is heated to a temperature in the range of 74 °C to 76 °C.
- the solvent used is 2-propanol and the slurry is heated to 75 °C.
- the heating of the slurry in the temperature range of 74 °C to 85 °C ensures better separation of racemic Indoxacarb in the heated slurry. This range of temperature is important because below 70 °C, separation of racemic Indoxacarb will be ineffective and above 85 °C, there might be loss of solvent in the slurry due to evaporation, depending upon the solvent used.
- the heated slurry is cooled to a temperature in the range of 55 °C to 70 °C to allow partial crystallization and obtain a warm slurry comprising crystals of racemic Indoxacarb.
- the racemic Indoxacarb has lower solubility than the enantiomeric Indoxacarb and hence crystallizes out partially in the cooling step.
- the removal of racemic Indoxacarb ensures that the inactive R-isomer is relatively reduced and the amount of S-isomer in the final composition is relatively higher than in the crude Indoxacarb.
- the heated slurry is cooled to a temperature in the range of 60 °C to 70 °C. In an embodiment, the heated slurry is cooled to 65 °C.
- At least one portion of the warm slurry is filtered at a temperature in the range of 55 °C to 70 °C to isolate a mass comprising the crystals of racemic Indoxacarb and obtain a filtrate.
- the at least one portion of the warm slurry is in the range of 10 vol.% to 20 vol.%. In an embodiment, 15 vol.% of the warm slurry is filtered.
- the warm slurry is cooled to 65 °C and the filtration is done at 65 °C.
- the filtrate is mixed with the remaining portion of the warm slurry to obtain a first mixture.
- the first mixture is cooled to a temperature in the range of 10 °C to 25 °C to initiate crystallization followed by equilibrating under stirring for a time period in the range of 3 hours to 8 hours at a temperature in the range of 10 °C to 25 °C to complete crystallization to obtain a second mixture containing enantiomeric crystals of Indoxacarb comprising R-isomer and S-isomer of Indoxacarb.
- the cooling of the filtrate is done by using external source of cooling.
- the step of cooling the filtrate initiates crystallization of the enantiomeric mixture of Indoxacarb.
- equilibration is the process of allowing a solution to attain equilibrium for obtaining a specific enantiomeric ratio.
- the equilibration step is very important for allowing complete crystallization of the enantiomeric mixture, while the impurities stay in the filtrate.
- the cooling of the filtrate and the equilibration of the second mixture is done at a temperature in the range of 15 °C to 20 °C.
- the filtrate is cooled to 17 °C and the equilibration of the second mixture is done at 17 °C.
- the equilibration is done for a time period in the range of 5 hours to 8 hours. In an embodiment, the equilibration is done for 6 hours.
- the mixture is filtered to isolate the enantiomeric crystals of Indoxacarb.
- the crystals are washed and dried to obtain an enantiomeric mixture of Indoxacarb crystals having purity in the range of 95% to 99.5%.
- the enantiomeric mixture of Indoxacarb comprises crystals of R-isomer and S-isomer, wherein the S-isomer crystals are present in an amount in the range of 75% to 90% of the enantiomeric mixture.
- the step of washing the crystals is done using a fluid medium selected from the group consisting of methanol, ethanol, 2-propanol, 1 -butanol and cyclohexanol.
- a fluid medium selected from the group consisting of methanol, ethanol, 2-propanol, 1 -butanol and cyclohexanol.
- the washing of the crystals with the fluid medium ensures complete removal of the impurities in the filtrate, thereby leading to higher purity.
- the crystals are washed using 2-propanol.
- the step of drying the mass is done under vacuum at a temperature in the range of 35 °C to 45 °C.
- the temperature range of drying ensures the removal of the fluid medium from the crystals. In an embodiment, the drying is done at 40 °C.
- the enantiomeric mixture of Indoxacarb crystals obtained by the process of the present disclosure has a purity of 98% and the S-isomer crystals are present in an amount of 75% of the enantiomeric mixture. In another embodiment, the enantiomeric mixture of Indoxacarb crystals obtained by the process of the present disclosure has a purity of 99% and the S-isomer crystals are present in an amount of 86% of the enantiomeric mixture.
- crude Indoxacarb is mixed with 2-propanol to obtain a slurry, wherein the crude Indoxacarb comprises impurities in an amount of 13 wt.%.
- the slurry is heated to 75 °C to obtain a heated slurry.
- the heated slurry is cooled to 65 °C to allow partial crystallization and obtain a warm slurry comprising crystals of racemic Indoxacarb.
- At least one portion of the warm slurry is filtered at 65 °C, to isolate a mass comprising the crystals of racemic Indoxacarb and obtain a filtrate.
- the filtrate is mixed with the remaining portion of the warm slurry to obtain a first mixture.
- the first mixture is cooled to 17 °C to initiate crystallization followed by equilibration under stirring for 6 hours at 17 °C to allow complete crystallization to obtain a second mixture containing enantiomeric crystals of Indoxacarb comprising R-isomer and S-isomer of Indoxacarb.
- the second mixture is filtered to isolate the enantiomeric crystals of Indoxacarb.
- the crystals are washed with 2-propanol and dried at 40 °C under vacuum, to obtain an enantiomeric mixture of Indoxacarb crystals having purity in the range of 95% to 99.5%.
- the present disclosure provides an enantiomeric mixture of Indoxacarb crystals having purity in the range of 95% to 99.5%, wherein the enantiomeric mixture of Indoxacarb crystals comprises crystals of R-isomer and S-isomer of Indoxacarb.
- the S- isomer crystals are present in the range of 75 % to 90% of the enantiomeric mixture.
- the enantiomeric mixture of Indoxacarb crystals has a purity of 99% and the S-isomer crystals are present in an amount of 80% of the enantiomeric mixture.
- the enantiomeric mixture of Indoxacarb crystals obtained by the process of the present disclosure has a purity of 99% and the S-isomer crystals are present in an amount of 86% of the enantiomeric mixture.
- the commercial sample of Indoxacarb comprises 1:3 ratio of R:S isomers.
- the conventional process of enhancing the purity leads to reduction in the amount of the active S-isomer.
- the process of the present disclosure leads to the enhancement in the purity of Indoxacarb while increasing or maintaining the amount of the active S-isomer, thereby avoiding any deterioration in the amount of the active isomer.
- Example a Isolation of racemic Indoxacarb (Sample 1A) and enantiomeric crystals of Indoxacarb (Sample 2A)
- the slurry was heated to 75 °C to obtain a heated slurry, which was then cooled to 70°C to allow partial crystallization and obtain a warm slurry comprising crystals of racemic Indoxacarb. 10 vol.% of the warm slurry was then filtered at 70°C to isolate a mass comprising the crystals of racemic Indoxacarb and obtain a filtrate.
- Example 1A The racemic Indoxacarb crystals were dried (11 gm) and used for further analysis (Sample 1A). The filtrate was mixed with the remaining slurry and cooled to 18 °C to initiate crystallization followed by equilibrating under stirring for 4 hours to allow complete crystallization to obtain a mixture containing enantiomeric crystals of Indoxacarb comprising R-isomer and S-isomer of Indoxacarb. The mixture was filtered at 18 °C to isolate the enantiomeric crystals of Indoxacarb.
- Example b Isolation of racemic Indoxacarb (Sample IB) and enantiomeric crystals of Indoxacarb (Sample 2B)
- the slurry was heated to 75 °C to obtain a heated slurry, which was cooled to 60°C to allow partial crystallization and obtain a warm slurry comprising crystals of racemic Indoxacarb. 15 vol.% of the warm slurry was then filtered at 60°C to isolate a mass comprising the crystals of racemic Indoxacarb and obtain a filtrate.
- the racemic Indoxacarb crystals were dried (15 gm) and used for further analysis (Sample IB).
- Example c Isolation of racemic Indoxacarb (Sample 1C) and enantiomeric crystals of Indoxacarb (Sample 2C)
- the slurry was heated to 75 °C to obtain a heated slurry, which was cooled to 70°C to allow partial crystallization and obtain a warm slurry comprising crystals of racemic Indoxacarb. 15 vol.% of the warm slurry was then filtered at 70°C to isolate a mass comprising the crystals of racemic Indoxacarb and obtain a filtrate.
- Example 1C The racemic Indoxacarb crystals were dried (14 gm) and used for further analysis (Sample 1C). The filtrate was mixed with the remaining slurry and cooled to 16 °C to initiate crystallization followed by equilibrating under stirring for 6 hours to allow complete crystallization to obtain a mixture containing enantiomeric crystals comprising R-isomer and S -isomer of Indoxacarb. The mixture was filtered at 16 °C to separate the enantiomeric crystals of Indoxacarb.
- Example d Isolation of racemic Indoxacarb (Sample ID) and enantiomeric crystals of Indoxacarb (Sample 2D)
- the slurry was heated to 75 °C to obtain a heated slurry, which was cooled to 70°C to allow partial crystallization and obtain a warm slurry comprising crystals of racemic Indoxacarb.
- 20 vol.% of warm slurry was then filtered at 65 °C to isolate a mass comprising the crystals of racemic Indoxacarb and obtain a filtrate.
- the racemic Indoxacarb crystals were dried (15 gm) and used for further analysis (Sample ID).
- Example 1A The racemic Indoxacarb crystals (sample 1A) and enantiomeric Indoxacarb crystals (sample 2A), as obtained from Example (a) were subjected to Differential scanning calorimetry (DSC) analysis as shown in Figures 1 and 2 respectively.
- DSC Differential scanning calorimetry
- sample 1A shows a single peak in the range of 144.5 °C to 150.7 °C, corresponding to the melting temperature of racemic Indoxacarb
- DSC analysis of sample 2A shows two peaks, wherein a peak in the range of 87.5 °C to 93.6 °C corresponds to the enantiomeric Indoxacarb (S-isomer or R-isomer) and a peak in the range of 143.1 °C to 147.3 °C, corresponds to the racemic Indoxacarb.
- the samples 1A and 2A, as obtained from Example (a) were subjected to X-Ray Diffraction (XRD) analysis as shown in Figures 3 and 4 respectively.
- XRD X-Ray Diffraction
- the sample 2A shows most of the significant expected peaks, thus confirming the presence of the crystalline form of Indoxacarb.
- the process of the present disclosure is simple and effective wherein the enhancement in purity does not decrease the amount of S-isomer.
- the Indoxacarb crystals obtained by the process of the present disclosure have higher purity and either same or higher amount of the S-isomer than the crude Indoxacarb.
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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BR112022000300A BR112022000300A2 (en) | 2019-07-10 | 2020-07-09 | Process to obtain indoxacarb crystals with specific purity and enantiomeric ratio |
AU2020311059A AU2020311059A1 (en) | 2019-07-10 | 2020-07-09 | A process for obtaining Indoxacarb crystals with specific purity and enantiomeric ratio |
EP20837895.0A EP3997074A4 (en) | 2019-07-10 | 2020-07-09 | A process for obtaining indoxacarb crystals with specific purity and enantiomeric ratio |
CONC2022/0001267A CO2022001267A2 (en) | 2019-07-10 | 2022-02-08 | A process for obtaining indoxacarb crystals with specific purity and enantiomeric ratio |
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IN201921027683 | 2019-07-10 | ||
IN201921027683 | 2019-07-10 |
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EP (1) | EP3997074A4 (en) |
AU (1) | AU2020311059A1 (en) |
BR (1) | BR112022000300A2 (en) |
CO (1) | CO2022001267A2 (en) |
WO (1) | WO2021005545A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116003342A (en) * | 2022-01-05 | 2023-04-25 | 山东京博农化科技股份有限公司 | Method for obtaining indoxacarb and indoxacarb preparation |
WO2023148735A1 (en) | 2022-02-02 | 2023-08-10 | Adama Makhteshim Ltd. | Novel solid state forms of indoxacarb |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IN2005MU00530A (en) * | 2005-05-02 | 2005-11-14 | Gharda Chemicals Ltd | |
CN104311502A (en) * | 2014-09-15 | 2015-01-28 | 南通施壮化工有限公司 | Method for separation purification of indoxacarb S-isomer from indoxacarb mixture |
-
2020
- 2020-07-09 AU AU2020311059A patent/AU2020311059A1/en active Pending
- 2020-07-09 WO PCT/IB2020/056457 patent/WO2021005545A1/en unknown
- 2020-07-09 EP EP20837895.0A patent/EP3997074A4/en active Pending
- 2020-07-09 BR BR112022000300A patent/BR112022000300A2/en unknown
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- 2022-02-08 CO CONC2022/0001267A patent/CO2022001267A2/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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IN2005MU00530A (en) * | 2005-05-02 | 2005-11-14 | Gharda Chemicals Ltd | |
CN104311502A (en) * | 2014-09-15 | 2015-01-28 | 南通施壮化工有限公司 | Method for separation purification of indoxacarb S-isomer from indoxacarb mixture |
Non-Patent Citations (1)
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See also references of EP3997074A4 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116003342A (en) * | 2022-01-05 | 2023-04-25 | 山东京博农化科技股份有限公司 | Method for obtaining indoxacarb and indoxacarb preparation |
CN116003342B (en) * | 2022-01-05 | 2024-04-05 | 山东京博农化科技股份有限公司 | Method for obtaining indoxacarb and indoxacarb preparation |
WO2023148735A1 (en) | 2022-02-02 | 2023-08-10 | Adama Makhteshim Ltd. | Novel solid state forms of indoxacarb |
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EP3997074A4 (en) | 2023-07-05 |
EP3997074A1 (en) | 2022-05-18 |
BR112022000300A2 (en) | 2022-03-15 |
AU2020311059A1 (en) | 2022-03-03 |
CO2022001267A2 (en) | 2022-05-20 |
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