Patent Description:
Effective control of insect pest such as arthropods is essential for crop safety. Arthropods are an important class of pests which cause huge damage to crop and household every year around the world. Anthranilamides are a new class of compounds with extremely potent insecticidal activity. These nitrogen-containing aromatic compounds selectively act on targeted ryanodine receptors in insects. Ryanodine receptors form calcium ion channels which are responsible for muscle function.

Examples of insecticidal anthranilamides are cyantraniliprole, chlorantraniliprole, cyclaniliprole, tetrachlorantraniliprole and tetraniliprole. Chlorantraniliprole is a highly potent and selective activator of insect ryanodine receptor with exceptional activity on a broad range of Lepidoptera. It controls a wide range of chewing pests (primarily Lepidoptera, but also some Coleoptera, Diptera and Isoptera species) in a broad range of crops, including fruit, vegetables, vines, cotton, sugar cane, rice and grass.

<CIT> describes an arthropod pests control composition and a method for controlling arthropod pests. The composition comprises, inter alia, <NUM>-oxo-<NUM>-[(<NUM>-phenylethyl)amino]-butyric acid.

<CIT> describes polysubstituted pyridyl pyrazolecarboxamides and preparation methods and uses of these compounds.

<CIT> relates to a pest controlling composition and a method for controlling pests.

<CIT> relates to invertebrate pest control mixtures comprising a biologically effective amount of an anthranilamide, an N-oxide or a salt thereof and at least one other invertebrate pest control agent.

<CIT> relates to a method for preparing <NUM>-aminobenzamides and derivatives thereof.

<NPL>) describes various physical and chemical characteristics, use patterns and formulations, toxicological properties and environmental hazards of chlorantraniliprole.

<NPL>, describes a high-throughput multipesticides residue analysis in earthworms.

<CIT> describes <NUM>-substituted pyridyl-pyrazolyl amide compounds.

<CIT> describes a process for preparing substituted isatoic acid anhydride compounds and derivatives thereof.

<CIT> describes tetrazole-substituted anthranilamides.

<CIT> discloses the preparation of chlorantraniliprole represented as compound of Formula IV (Scheme I).

Intermediate <NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazole-<NUM>-carboxylic acid is represented as compound of Formula I and intermediate <NUM>-amino-<NUM>-chloro-<NUM>-methylbenzoic acid is represented as compound of Formula II. <NUM>-[<NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazol-<NUM>-yl]-<NUM>-chloro-<NUM>-methyl-<NUM>-<NUM>,<NUM>-benzoxazin-<NUM>-one is referred to as compound of Formula III.

<CIT> discloses the preparation of cyantraniliprole (Formula represented as compound of Formula VII (Scheme II).

Intermediate <NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazole-<NUM>-carboxylic acid is represented as compound of Formula I and intermediate <NUM>-amino-<NUM>-cyano-<NUM>-methylbenzoic acid is represented as compound of Formula V. <NUM>-[<NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazol-<NUM>-yl]-<NUM>-cyano-<NUM>-methyl-<NUM>-<NUM>,<NUM>-benzoxazin-<NUM>-one is referred to as compound of Formula VI.

Inventors of the present invention noted that compound of Formula III (<NUM>-[<NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazol-<NUM>-yl]-<NUM>-chloro-<NUM>-methyl-<NUM>-<NUM>,<NUM>-benzoxazin-<NUM>-one) is not physically stable enough to undergo appropriate purification. It has been further noted that impure compound of Formula III on further reaction with methyl amine, leads to chlorantraniliprole with inconsistent physical and chemical properties which in turn leads to ineffective product for the intended use.

Further, it has been observed that low solubility of anthranilamides in water and/or organic solvents makes it challenging to conduct appropriate purification processes.

Therefore, there is a need to develop improved preparation and purification methods for anthranilamides.

It is an object of the present invention to provide anthranilamides that is free of impurities.

It is an object of the present invention to provide a process for preparation of certain anthranilamides.

It is another object of the present invention to provide a process for preparing chlorantraniliprole that is free from impurities.

The present invention provides a process for purifying compound of Formula A,
<CHM>.

The present invention also provides a process for purifying chlorantraniliprole from an aqueous slurry of Chlorantraniliprole, said process comprising the steps of:.

The present invention also provides a process for preparing chlorantraniliprole that is free from impurities, said process comprising the steps of:.

The present invention also provides a process for purifying cyantraniliprole from an aqueous slurry of cyantraniliprole, said process comprising the steps of:.

wherein cyantraniliprole is purified from an aqueous slurry of cyantraniliprole.

The present invention also provides a process for preparing cyantraniliprole having a purity of at least about <NUM>% and, said process comprising the steps of:.

wherein the compound of Formula VI is <NUM>-[<NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazol-<NUM>-yl]-<NUM>-cyano-<NUM>-methyl-<NUM>-<NUM>,<NUM>-benzoxazin-<NUM>-one.

The compound of Formula I is <NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazole-<NUM>-carboxylic acid.

The compound of Formula II is <NUM>-amino-<NUM>-chloro-<NUM>-methylbenzoic acid.

Disclosed herein are compounds of Formula (A) that are substantially free from impurities:
<CHM>
wherein R<NUM>, R<NUM>, R<NUM> and R<NUM> can be independently a hydrogen, halogen, cyano, amino, N-thio derivatives, hydroxyl, unsubstituted or substituted linear or branched (C<NUM>-C<NUM>) alkyl or cycloalkyl, heterocyclic unsubstituted or substituted with halogen, cyano, amino, hydroxyl or linear or branched (C<NUM>-C<NUM>) alkyl and wherein m, n, p and q can be <NUM>, <NUM>, <NUM>, or <NUM>.

A process for purifying compound of Formula A,
<CHM>.

Also disclosed herein is chlorantraniliprole substantially free of impurities.

A process for purifying chlorantraniliprole as disclosed herein may comprise purifying Chlorantraniliprole from an aqueous slurry comprising Chlorantraniliprole.

A process for purifying chlorantraniliprole as disclosed herein may comprise the steps of:.

A process preparing chlorantraniliprole that is free from impurities as disclosed herein may comprise purifying Chlorantraniliprole from an aqueous slurry comprising the reaction product of the compound of formula III with methylamine.

A process preparing chlorantraniliprole that is free from impurities as disclosed herein may comprise the steps of:.

In a process for preparing chlorantraniliprole that is substantially free from impurities as disclosed herein, purification of compound of Formula III is not essential.

A process for preparing chlorantraniliprole that is substantially free from impurities as disclosed herein may comprise purifying Chlorantraniliprole from an aqueous slurry, said aqueous slurry comprising a hydrophilic solvent admixed with the reaction product of a compound of formula III with methylamine.

A process for preparing chlorantraniliprole that is substantially free from impurities as disclosed herein may comprise the steps of:.

Also disclosed herein is a process for purifying cyantraniliprole, said process comprising purifying cyantraniliprole from an aqueous slurry of cyantraniliprole.

A process for purifying cyantraniliprole as disclosed herein may comprise the steps of:.

A process for preparing cyantraniliprole that is free from impurities may comprise the steps of:.

A process for preparing cyantraniliprole as disclosed herein may comprise purifying cyantraniliprole from an aqueous slurry, said aqueous slurry comprising a hydrophilic solvent admixed with the reaction product of a compound of formula VI with methylamine.

It has been noted that many of the anthranilamides represented by general structure of Formula A have low solubility in water or in other hydrophilic solvents due to which isolation and purification of the compound is troublesome. Despite their low solubility in water and other hydrophilic solvents, it has been surprisingly found by the present inventors that substantially pure anthranilamides i.e. which is substantially free of impurities, could be prepared by purifying the crude reaction product of the compound of formula III with methylamine, out of an aqueous slurry. Based on this finding, it has been made possible by the present inventors to provide insecticidal anthranilamides that is free from impurities and to a process for preparing such substantially pure anthranilamides.

Chlorantraniliprole is an example of such anthranilamides which is difficult to prepare and to purify resulting in varying physico-chemical properties and to optimize the process for its preparation. It has been noted that compound of formula III is not stable enough to undergo effective purification processes and that previous processes that depended upon purifying the compound of formula III to obtain pure anthranilamides failed to provide such substantially pure anthranilamides and lead to yield loss, as has been made possible by the process of the present invention. Impure compound of formula III on reacting further with methyl amine leads to chlorantraniliprole with various impurities and uneven physical properties and found to be ineffective for the intended use. The present invention finds that purifying the anthranilamides out of an aqueous slurry is a surprisingly better strategy to prepare substantially pure anthanilamides than starting with pure compound of formula III.

Inventors of the present invention noted that, by following the process of the present invention, purification of compound of formula III can be avoided or is not required and chlorantraniliprole could still be obtained that is substantially free from impurities.

The compound of Formula III is <NUM>-[<NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazol-<NUM>-yl]-<NUM>-chloro-<NUM>-methyl-<NUM>-<NUM>,<NUM>-benzoxazin-<NUM>-one.

The compound of Formula VI is <NUM>-[<NUM>-bromo-<NUM>-(<NUM>-chloropyridin-<NUM>-yl)-<NUM>-pyrazol-<NUM>-yl]-<NUM>-cyano-<NUM>-methyl-<NUM>-<NUM>,<NUM>-benzoxazin-<NUM>-one.

Disclosed herein are compounds of Formula (A) that is free from impurities.

Wherein R<NUM>, R<NUM>, R<NUM> and R<NUM> can be independently a hydrogen, halogen, cyano, amino, N-thio derivatives, hydroxyl, unsubstituted or substituted linear or branched (C<NUM>-C<NUM>) alkyl or cycloalkyl, heterocyclic unsubstituted or substituted with halogen, cyano, amino, hydroxyl or linear or branched (C<NUM>-C<NUM>) alkyl or linear or branched (C<NUM>-C<NUM>) alkyl and wherein m, n, p and q can be <NUM>, <NUM>, <NUM>, or <NUM>.

In such a process, the aqueous slurry of the compound of formula A can be provided in a reactor.

In such a process, the aqueous slurry of the compound of formula A may comprise a reaction product mixture which comprises the compound of formula A.

In an embodiment of invention, the reaction product mixture is a reaction product of a compound of formula III with methylamine.

In an embodiment of the invention, the reaction product mixture is a reaction product of a compound of formula III with methylamine carried out in an organic solvent.

In an embodiment of the invention, the compound of formula III is reacted with methylamine without being purified or isolated.

In an embodiment, the compound of formula III is a reaction product produced from a reaction between a compound of formula I and a compound of formula II.

In an embodiment, the compound of formula III is a reaction product produced from a reaction between a compound of formula I and a compound of formula II carried out in an organic solvent.

In an embodiment, the compound of formula III is used without being isolated or purified from a reaction between a compound of formula I and a compound of formula II carried out in an organic solvent.

In an embodiment of the invention, purifying the compound of formula A from an aqueous slurry comprising said compound of formula A may comprise repeatedly: (a) stirring the aqueous slurry for a predetermined time, (b) purifying said compound of formula A, and (c) separating said compound of formula A from the aqueous slurry.

In an embodiment of the invention, steps (a), (b) and (c) may be repeated a plurality of times.

Purifying the compound of formula A from an aqueous slurry comprising said compound of formula A may comprise stirring the aqueous slurry for a predetermined time, purifying said compound of formula A, separating said compound of formula A from the aqueous slurry, and drying said separated compound of formula A.

wherein said aqueous conditions comprise water or a mixture of water and one or more solvents.

In an embodiment, the compound of Formula A is when R<NUM>, R<NUM>, R<NUM> and R<NUM> can be independently a hydrogen, halogen, cyano, amino, N-thio derivatives, alkyl, substituted alkyl with halogen, cyano or amino heterocyclic unsubstituted or substituted with halogen, cyano, amino, hydroxyl or linear or branched (C<NUM>-C<NUM>) alkyl compounds wherein m, n, p and q can be <NUM>, <NUM>, <NUM>, or <NUM>.

In one embodiment, the compound of Formula A is when R<NUM> is CN, and CH<NUM>, R<NUM> is Cl, R<NUM> is Br and R<NUM> is H and -CH<NUM> wherein m and q=<NUM> as represented in the below structure.

In another embodiment, the compound of Formula A is when R<NUM> is Cl and -CH<NUM>, R<NUM> is Cl, R<NUM> is Br and R<NUM> is H and -CH<NUM> wherein m and q =<NUM> as represented in the below structure.

In another embodiment, the compound of Formula A is when R<NUM> is Cl and Br, R<NUM> is Cl, R<NUM> is Br and R<NUM> is H and <NUM>-cyclopropyl ethyl and wherein m and q =<NUM> as represented in the below structure.

In yet another embodiment, the compound of Formula A is when R<NUM> is Cl, R<NUM> is Cl, R<NUM> is Br and R<NUM> is H, and -CH<NUM>, wherein m, n and q =<NUM> as represented in the below structure.

In another embodiment, the compound of Formula A is when R<NUM> is CN, and -CH<NUM>, R<NUM> is Cl, R<NUM> is <NUM>-(trifluoromethyl)-<NUM>-tetrazol-<NUM>-yl] methyl and R<NUM> is H and -CH<NUM> wherein m and q =<NUM> as represented in the below structure.

In an embodiment, the term 'impurities' refers to unreacted synthetic intermediates, reagents, solvents, organic and/or inorganic products of side reactions, organic and/or inorganic salts and/or other undesired materials.

Therefore, the compounds of the invention being substantially free of impurities is intended to mean the referred compound being substantially free of all the unreacted synthetic intermediates, reagents, solvents, organic and/or inorganic products of side reactions, organic and/or inorganic salts and/or other undesired materials.

In an embodiment, aqueous conditions of step b) refers to water or a mixture of water and one or more solvents.

In a preferred embodiment, aqueous conditions of step b) refers to water.

In an embodiment, slurry of step b) is prepared by mixing reaction mass with water or with a mixture of water and one or more solvents.

In an embodiment, solvents are selected from the group comprising methanol, ethanol n-propanol, n-butanol, acetone, ethyl acetate, dimethyl sulfoxide, acetonitrile and dimethylformamide.

In a preferred embodiment, in step c), the reaction mass is stirred at a temperature from about <NUM> to about <NUM>.

In an embodiment, in step c), the reaction mass is stirred for a period of at least <NUM> minutes.

In a preferred embodiment, in step c), the reaction mass is stirred for a period of at least <NUM> minutes.

In an embodiment, the solid separation of step d) is conducted by filtration, sedimentation, decantation, or by solid-liquid centrifugation.

In a preferred embodiment the solid separation of step d) is conducted by filtration.

The process of the present invention can provide chlorantraniliprole substantially free of impurities.

The process of the present invention can provide chlorantraniliprole that is substantially free of impurities.

The process of the present invention can provide cyantraniliprole that is substantially free of impurities.

The process of the present invention can provide chlorantraniliprole with purity > <NUM>% by weight.

The process of the present invention can provide cyantraniliprole with purity > <NUM>% by weight.

In another embodiment, synthetic intermediates comprise compound of Formula I, compound of Formula II and compound of Formula III.

In another embodiment, synthetic intermediates comprise compound of Formula I, compound of Formula V and compound of Formula VI.

In an embodiment, reagent include methane sulfonyl chloride and methyl amine.

In an embodiment, the organic and/or inorganic products of side reactions include salts of compound of Formula I with sulfonic acids and/or chlorides.

In an embodiment organic and/or inorganic products of side reactions include salts of compound of Formula I with methane sulfonyl chloride.

In another embodiment organic and/or inorganic products of side reactions include salts of compound of Formula II with sulfonic acids and/or chlorides.

In another embodiment organic and/or inorganic products of side reactions include salts of compound of Formula V with sulfonic acids and/or chlorides.

In yet another embodiment, the process of the present invention can provide chlorantraniliprole that is substantially free of compound of Formula I, compound of Formula II, compound of Formula III, salts of compound of Formula I with sulfonic acids and chlorides.

In yet another embodiment, the process of the present invention can provide cyantraniliprole that is substantially free of compound of Formula I, compound of Formula V, compound of Formula VI, salts of compound of Formula I with sulfonic acids and chlorides.

A process for purifying chlorantraniliprole as herein disclosed, may comprise purifying Chlorantraniliprole from an aqueous slurry comprising Chlorantraniliprole.

The aqueous slurry of Chlorantraniliprole may be provided in a reactor.

The aqueous slurry of Chlorantraniliprole may comprise a reaction product mixture which comprises Chlorantraniliprole.

In an embodiment of the invention, the reaction product mixture is a reaction product of a compound of formula III with methylamine.

In an embodiment, the reaction product mixture is a reaction product of a compound of formula III with methylamine carried out in an organic solvent.

In an embodiment, the compound of formula III is reacted with methylamine without being purified or isolated.

In an embodiment, the aqueous slurry comprises a slurry comprises the reaction product mixture in water.

In an embodiment, purifying Chlorantraniliprole from an aqueous slurry comprising Chlorantraniliprole comprises stirring the aqueous slurry for a predetermined time before purifying said Chlorantraniliprole.

Purifying Chlorantraniliprole from an aqueous slurry comprising Chlorantraniliprole may comprise stirring the aqueous slurry for a predetermined time, and subsequently purifying said Chlorantraniliprole.

Purifying Chlorantraniliprole from an aqueous slurry comprising said Chlorantraniliprole may comprises stirring the aqueous slurry for a predetermined time, purifying said Chlorantraniliprole, and separating said Chlorantraniliprole from the aqueous slurry.

Purifying Chlorantraniliprole from an aqueous slurry comprising said Chlorantraniliprole may comprise repeatedly: (a) stirring the aqueous slurry for a predetermined time, (b) purifying said Chlorantraniliprole, and (c) separating Chlorantraniliprole from the aqueous slurry.

Steps (a), (b) and (c) may be repeated a plurality of times.

Purifying Chlorantraniliprole from an aqueous slurry comprising said Chlorantraniliprole may comprise stirring the aqueous slurry for a predetermined time, purifying Chlorantraniliprole, separating Chlorantraniliprole from the aqueous slurry, and drying said separated Chlorantraniliprole.

Thus, the present invention provides a process for purifying chlorantraniliprole, said process comprising the steps of:.

In an embodiment, chlorantraniliprole of step a) can be prepared from a reaction of compound of Formula I, its derivatives or salts and compound of Formula II, its derivatives or salts.

In another embodiment, the process for purifying chlorantraniliprole comprises the steps of:.

In yet another embodiment, the process for purifying chlorantraniliprole comprises the steps of:.

The reaction product mixture may be a reaction product of a compound of formula III with methylamine.

The aqueous slurry comprising a slurry may comprise the reaction product mixture in water.

Purifying Chlorantraniliprole from an aqueous slurry comprising Chlorantraniliprole may comprise stirring the aqueous slurry for a predetermined time before purifying said Chlorantraniliprole.

Purifying Chlorantraniliprole from an aqueous slurry comprising said Chlorantraniliprole may comprise stirring the aqueous slurry for a predetermined time, purifying said Chlorantraniliprole and separating said Chlorantraniliprole from the aqueous slurry.

A process for purifying cyantraniliprole as disclosed herein may comprise purifying cyantraniliprole from an aqueous slurry of cyantraniliprole.

The present invention provides a process for purifying cyantraniliprole said process comprising the steps of:.

The present invention also provides a process for preparing chlorantraniliprole that is substantially free from impurities, said process comprising the steps of:.

wherein purification of compound of Formula III is not essential.

In an embodiment, reaction of step a) is conducted in an organic solvent selected from the group comprising acetonitrile, tetrahydrofuran, ethyl acetate, toluene, xylene and dioxane.

In a preferred embodiment reaction of step a) is conducted in ethyl acetate.

In an embodiment, in step a) methyl amine is used as an aqueous solution.

In an embodiment, aqueous conditions of step c) refers to water or a mixture of water and one or more solvents.

In a preferred an embodiment, aqueous conditions of step c) refers to water.

In an embodiment, slurry of step c) is prepared by mixing reaction mass with water or with a mixture of water and one or more solvents.

In a preferred embodiment, in step d), the reaction mass is stirred at a temperature from about <NUM> to about <NUM>.

In an embodiment, in step d), the reaction mass is stirred for a period of at least <NUM> minutes.

In a preferred embodiment, in step d), the reaction mass is stirred for a period of at least <NUM> minutes.

In an embodiment, the solid separation of step e) is conducted by filtration, sedimentation, decantation, or by solid-liquid centrifugation.

In a preferred embodiment the solid separation of step e) is conducted by filtration.

The present invention also provides a process for preparing chlorantraniliprole that is substantially free from impurities, said process comprising purifying Chlorantraniliprole from an aqueous slurry, said aqueous slurry comprising a hydrophilic solvent admixed with the reaction product of a compound of formula III with methylamine.

In an embodiment, hydrophilic solvents are selected from the group comprising methanol, ethanol n-propanol, n-butanol, acetone, ethyl acetate, dimethyl sulfoxide, acetonitrile and dimethylformamide.

In one embodiment of the invention, the process for preparing chlorantraniliprole that is substantially free from impuritiescomprises the steps of:.

In another embodiment reaction of step a) is conducted in presence of a base.

In an embodiment, step b) purification of compound of Formula III can be optional.

In another embodiment, in step (b), compound of Formula III can be purified partially.

In yet another embodiment, according to the present invention, purification of compound of Formula III is not essential.

In an embodiment, step b) purification of compound of Formula III can be avoided.

In an embodiment, the process of the present invention leads to chlorantraniliprole that is substantially free from impurities which are produced during step a) reaction.

In another embodiment, the process of the present invention avoids the purification of less stable compound of Formula III.

In an embodiment, reaction of step c) is conducted in an organic solvent selected from the group comprising acetonitrile, tetrahydrofuran, ethyl acetate, toluene, xylene and dioxane.

In a preferred embodiment reaction of step c) is conducted in ethyl acetate.

In an embodiment, in step c) methyl amine is used as an aqueous solution.

In an embodiment, aqueous conditions of step e) refers to water or a mixture of water and one or more solvents.

In a preferred an embodiment, aqueous conditions of step e) refers to water.

In an embodiment, slurry of step e) is prepared by mixing reaction mass with water or with a mixture of water and one or more solvents.

In a preferred embodiment, the reaction mass is stirred at a temperature from about <NUM> to about <NUM>.

In an embodiment, in step f), the reaction mass is stirred for a period of at least <NUM> minutes.

In a preferred embodiment, in step f), the reaction mass is stirred for a period of at least <NUM> minutes.

In an embodiment, the solid separation of step g) is conducted by filtration, sedimentation, decantation, or by solid-liquid centrifugation.

In a preferred embodiment the solid separation of step g) is conducted by filtration.

The process of the present invention can provide Chlorantraniliprole having a purity of at least about <NUM>%.

The process of the present invention can provide an anthanilamide insecticide having less than <NUM>% of intermediates of formulae I, II, and III.

The process of the present invention can provide an anthranilamide insecticide having less than <NUM>% of intermediates of formulae I, II and III.

The process of the present invention can provide Chlorantraniliprole having less than <NUM>% of intermediates of formulae I, II, and III.

The process of the present invention can provide Chlorantraniliprole having less than <NUM>% of intermediates of formulae I, II and III.

The process of the present invention can provide an anthranilamide insecticide having less than <NUM>% of the salts of intermediates of formulae I, II, and III.

The process of the present invention can provide an anthranilamide insecticide having less than <NUM>% of the salts of intermediates of formulae I, II and III.

The process of the present invention can provide Chlorantraniliprole having less than <NUM>% of the salts of intermediates of formulae I, II, and III.

The process of the present invention can provide Chlorantraniliprole having less than <NUM>% of the salts of intermediates of formulae I, II and III.

The salts of intermediates of formulae I, II or III include the salts of these intermediates of methane sulfonyl chloride.

The process of the present invention can provide an anthranilamide insecticide having less than <NUM>% of the inorganic impurities.

The process of the present invention can provide Chlorantraniliprole having less than <NUM>% of the inorganic impurities.

A process for preparing cyantraniliprole that is free from impurities as disclosed herein may comprise the steps of:.

In one embodiment of the invention, the process for preparing cyantraniliprole comprises purifying cyantraniliprole from an aqueous slurry, said aqueous slurry comprising a hydrophilic solvent admixed with the reaction product of a compound of formula VI with methylamine.

The advantages and other parameters of the present invention is illustrated by the below given examples. However, the scope of the present invention is not limited by the examples in any manner. It will be appreciated by any person skilled in this art that the present invention includes aforesaid examples and further can be modified and altered within the technical scope of the present invention.

Methane sulphonyl chloride (<NUM>) in acetonitrile (<NUM>) was added to the mixture of compound of Formula I (<NUM>), compound of Formula II (<NUM>) and pyridine (<NUM>) in acetonitrile (<NUM>) with stirring at <NUM>-<NUM> followed by stirring for <NUM> hours at <NUM>. The mixture was then filtered and washed with acetonitrile followed by drying to get compound of Formula III (<NUM>, Yield = <NUM>%).

Compound of Formula III (<NUM>) was stirred in ethyl acetate (<NUM>) in a reactor at <NUM>-<NUM> while stirring. Aqueous solution of methyl amine (<NUM>) was added to the reaction mixture in <NUM> hours at <NUM>-<NUM> and stirred for <NUM> hours. The mass was then cooled to <NUM>, filtered and washed with ethyl acetate to get chlorantraniliprole (<NUM>, ~<NUM>%purity).

<NUM> of chlorantraniliprole (as prepared in example <NUM>) and <NUM> of water were charged into a reactor. The mass was stirred at <NUM>°-<NUM> for one hour. The mass was then filtered. The wet mass was then charged into the reactor and <NUM> of water was added. The slurry was then stirred at <NUM>°-<NUM> for one hour. The mass was then filtered and washed with hot water. The wet mass thus obtained was dried at <NUM>. <NUM>, purity <NUM>%.

Methane sulphonyl chloride (<NUM>) in Tetrahydrofuran (<NUM>) was added to the mixture of compound of Formula I (<NUM>), compound of Formula II (<NUM>) and pyridine (<NUM>) in Tetrahydrofuran (<NUM>) with stirring at <NUM>-<NUM> followed by stirring for <NUM> hours at <NUM>. The mixture was then filtered and washed with acetonitrile followed by drying to get compound of Formula III (<NUM>, Yield = <NUM>%).

Compound of Formula III (<NUM>) was stirred in ethyl acetate (<NUM>) in a reactor at <NUM>-<NUM> while stirring. Aqueous solution of methyl amine (<NUM>) was added to the reaction mixture in <NUM> hours at <NUM>-<NUM> and stirred for <NUM> hours. The mass was then cooled to <NUM>, Add <NUM> gms water and maintain for <NUM> hr then filtered and washed with ethyl acetate to get chlorantraniliprole (<NUM>, ~<NUM>%purity).

<NUM> of chlorantraniliprole (as prepared in example <NUM>) <NUM> of water and <NUM> of ethyl acetate were charged into a reactor. The mass was stirred at <NUM>°-<NUM> for one hour. The mass was then filtered and washed with hot water. The wet mass thus obtained was dried at <NUM>. <NUM>, purity <NUM>%.

The analytical results of chlorantraniliprole prepared (Example <NUM>) and purified (Example <NUM>) by the present invention is presented in the below table (Table <NUM>):.

Intermediates include compound of Formula I, compound of Formula II and compound of Formula III. Salts of intermediates include salt of compound of Formula I with methane sulfonyl chloride. Inorganics include chlorides. Traces of solvents, bases and other unidentified impurities are also getting removed by the process of the present invention. From the above experiments it is established that the process according to the present invention can be used to produce chlorantraniliprole of high purity as well as consistent properties.

Methane sulphonyl chloride (<NUM>) in acetonitrile (<NUM>) was added to the mixture of compound of Formula I (<NUM>), compound of Formula V (<NUM>) and pyridine (<NUM>) in acetonitrile (<NUM>) with stirring at <NUM>-<NUM> followed by stirring for <NUM> hours at <NUM>. The mixture was then filtered and washed with acetonitrile followed by drying to get compound of Formula VI (<NUM>, Yield = <NUM>%).

Compound of Formula VI (<NUM>) was stirred in ethyl acetate (<NUM>) in a reactor at <NUM>-<NUM> while stirring. Aqueous solution of methyl amine (<NUM>) was added to the reaction mixture in <NUM> hours at <NUM>-<NUM> and stirred for <NUM> hours. The mass was then cooled to <NUM>, filtered and washed with ethyl acetate to get cyantraniliprole (<NUM>, ~<NUM>%purity).

Claim 1:
A process for purifying compound of Formula A,
<CHM>
wherein R<NUM>, R<NUM>, R<NUM> and R<NUM> can be independently a hydrogen, halogen, cyano, amino, N-thio derivatives, hydroxyl, unsubstituted or substituted linear or branched (C<NUM>-C<NUM>) alkyl or cycloalkyl, heterocyclic unsubstituted or substituted with halogen, cyano, amino, hydroxyl or linear or branched (C<NUM>-C<NUM>) alkyl and wherein m, n, p and q can be <NUM>, <NUM>, <NUM>, or <NUM>; said process comprising the steps of:
a) feeding a reaction product mixture of compound of Formula A into a reactor;
b) preparing a slurry of the mixture in aqueous conditions;
c) stirring the slurry for a pre-determined time at a temperature of from <NUM> to <NUM>;
d) separating solids;
e) optionally repeating steps b), c) and d); and
f) drying to get purified compound of Formula A;
wherein said aqueous conditions comprise water or a mixture of water and one or more solvents.