Process for the preparation of trifloxystrobin

Abstract

The present invention relates to an improved process for the preparation of trifloxystrobin of formula (I), which is simple, economical, efficient, user and environment friendly, moreover commercially viable with higher yield and chemical purity. ##STR00001##

Claims

1. An improved process for the preparation of trifloxystrobin of formula (I), ##STR00009## comprising the steps of: a) preparing a 2-methyl benzene diazonium chloride having a formula (2) by reacting 1-amino-2-methylbenzene having a formula (1) with an alkali metal nitrite in the presence of hydrochloric acid; ##STR00010## b) obtaining a 2-methoxyimino-acetic acid having a formula (4) by reacting 2-oxoacetic acid having a formula (3) with methoxylamine hydrochloride in the presence of a base in a suitable solvent or mixture of solvents thereof; ##STR00011## c) selectively obtaining (E)-2-methoxyimino-2-(o-tolyl) acetic acid having a formula (5) by reacting a compound of aforesaid formula (2) with a compound of aforesaid formula (4) in the presence of a salt of an acid; or a base and a metal sulphate in a suitable solvent or mixture of solvents thereof; ##STR00012## d) obtaining selectively (E)-2-methoxyimino-2-(o-tolyl)acetic acid methyl ester having a formula (6) by reacting a compound of aforesaid formula (5) with methanol and an acid or thionyl chloride with or without a suitable solvent or mixture of solvents thereof; ##STR00013## e) selectively obtaining (E)-2-(2-halomethylphenyl)-2-methoxy iminoacetic acid methyl ester having a formula (7) by reacting a compound of aforesaid formula (6) with a metal halogenate or N-bromosuccinimide in presence of a base with or without a catalyst in a suitable solvent or mixture of solvents thereof; ##STR00014## f) obtaining the trifloxystrobin of formula (I) by reacting a compound of aforesaid formula (7) with a 1-(3-trifluoromethyl-phenyl)-ethanone oxime having a formula (8) in the presence of a base and with or without a phase transfer catalyst in a suitable solvent or mixture of solvents thereof ##STR00015##

2. The process as claimed in claim 1, wherein the said formula (2) is prepared in an in-situ manner.

3. The process as claimed in claim 1, wherein the metal nitrite used in step (a) is selected from sodium nitrite and potassium nitrite.

4. The process as claimed in claim 1, wherein the said base of step (b) is selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, potassium bicarbonate, and sodium bicarbonate.

5. The process as claimed in claim 1, wherein the said solvent used in step (b) is selected from the group consisting of water, methanol, ethanol, isopropyl alcohol, butanol, isobutanol, ethylene glycol, and a mixture thereof.

6. The process as claimed in claim 1, wherein the said salt of an acid of step (c) is selected from the group consisting of mono or di sodium, and mono or di potassium salts of carboxylic acids.

7. The process as claimed in claim 1, wherein the said base of step (c) is selected from the group consisting of sodium hydroxide, potassium hydroxide, potassium carbonate, potassium bicarbonate, sodium carbonate, and sodium bicarbonate.

8. The process as claimed in claim 1, wherein the said metal sulfate of step (c) is copper sulfate.

9. The process as claimed in claim 1, wherein the said solvent of step (c) is selected from the group consisting of heptane, monochlorobenzene, isoparaffinic hydrocarbon, and a mixture thereof.

10. The process as claimed in claim 1, wherein the said acid of step (d) is selected from the group consisting of sulfuric acid, and hydrochloric acid.

11. The process as claimed in claim 1, wherein the said solvent of step (d) is selected from the group consisting of monochlorobenzene, ethylene dichloride, dichlorobenzene, and a mixture thereof.

12. The process as claimed in claim 1, wherein the said metal halogenate of step (e) is selected from the group consisting of sodium bromate, sodium chlorate, sodium iodate, potassium bromate, potassium chlorate, and potassium iodate.

13. The process as claimed in claim 1, wherein the said catalyst of step (e) is selected from the group consisting of sodium bromide, potassium bromide, sodium iodide, potassium iodide, azobisisobutyronitrile, and a mixture thereof.

14. The process as claimed in claim 1, wherein the said base of step (e) is selected from the group consisting of sodium bisulfite, potassium bisulfite, sodium hydroxide, and potassium hydroxide.

15. The process as claimed in claim 1, wherein the said solvent of step (e) is a combination of water and a solvent selected from the group consisting of ethylene dichloride, dichloromethane, chloroform, monochlorobenzene, acetonitrile, diisopropyl ether, ethyl acetate, and a mixture thereof.

16. The process as claimed in claim 1, wherein the said base of step (f) is selected from the group consisting of sodium hydroxide, potassium hydroxide, potassium carbonate, and sodium carbonate.

17. The process as claimed in claim 1, wherein the said phase transfer catalyst of step (f) is selected from the group consisting of tetra-n-butylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium chloride, sodium iodide, and potassium iodide.

18. The process as claimed in claim 1, wherein the said solvent of step (f) is selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, xylene, toluene, monochlorobenzene, propionitrile, acetonitrile, and a mixture thereof.

19. The process as claimed in claim 1, wherein one or all the steps are performed in an in-situ manner.

20. A process for the preparation of trifloxystrobin of formula (I) as claimed in claim 1, ##STR00016## comprising the steps of: a) preparing a 2-methyl benzene diazonium chloride formula (2) by reacting 1-amino-2-methylbenzene having a formula (1) with sodium nitrite in the presence of hydrochloric acid; ##STR00017## b) obtaining a 2-methoxyimino-acetic acid having a formula (4) by reacting 2-oxoacetic acid having a formula (3) with methoxylamine hydrochloride in the presence of sodium carbonate in water; ##STR00018## c) selectively obtaining (E)-2-methoxyimino-2-(o-tolyl)acetic acid having a formula (5) by reacting a compound of aforesaid formula (2) with a compound of aforesaid formula (4) in the presence of a sodium carbonate and a copper sulfate in a mixture of water and heptane; ##STR00019## d) obtaining selectively (E)-2-methoxyimino-2-(o-tolyl)acetic acid methyl ester having a formula (6) by reacting a compound of aforesaid formula (5) with methanol and sulfuric acid; ##STR00020## e) selectively obtaining (E)-2-(2-bromomethylphenyl)-2-methoxy iminoacetic acid methyl ester having a formula (7) by reacting a compound of aforesaid formula (6) with a sodium bromate and sodium bisulfite in water; ##STR00021## f) obtaining trifloxystrobin of formula (I) by reacting a compound of aforesaid formula (7) with a 1-(3-trifluoromethyl-phenyl)-ethanone oxime having a formula (8) in the presence of potassium carbonate and tetra-n-butylammonium bromide in acetone; ##STR00022##

Description

DETAILED DESCRIPTION OF THE INVENTION

(1) The present invention now will be described more fully hereinafter. The invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein; rather, these embodiments are provided so that this disclosure will satisfy applicable legal requirements. As used in the specification, and in the appended claims, the singular forms “a”, “an”, “the”, include plural referents unless the context clearly indicates otherwise.

(2) In accordance with the objectives, wherein the present invention provides an improved process for the preparation of trifloxystrobin of formula (I) and single isomeric form of (E)-2-methoxyimino-2-(o-tolyl)acetic acid (compound 5).

(3) In an embodiment of the present invention, wherein the said alkali metal nitrite used in step (a) is preferably selected from the group consisting of sodium nitrite (NaNO.sub.2), potassium nitrite (KNO.sub.2) and the like; most preferably sodium nitrite.

(4) In another embodiment of the present invention, wherein the acid of step (a) is preferably selected from the group consisting of hydrochloric acid (HCl), sulfuric acid (H.sub.2SO.sub.4) and the like; most preferably hydrochloric acid.

(5) In another embodiment of present invention, wherein the compound of step (a) having a formula (2) is prepared in in-situ manner.

(6) In another embodiment of the present invention, wherein the said base of step (b) is preferably selected from the group consisting of sodium hydroxide (NaOH), potassium hydroxide (KOH), potassium carbonate (K.sub.2CO.sub.3), potassium bicarbonate (KHCO.sub.3), sodium carbonate (Na.sub.2CO.sub.3), sodium bicarbonate (NaHCO.sub.3) and the like; most preferably sodium hydroxide or sodium carbonate.

(7) In another embodiment of the present invention, wherein the said solvent used in step (b) is preferably selected from the group consisting of water, methyl alcohol, ethyl alcohol, isopropyl alcohol, butanol, isobutanol, ethylene glycol and the like or mixture of solvents thereof; most preferably water.

(8) In another embodiment of the present invention, wherein the said salt of acid of step (c) is preferably selected from the group consisting of mono or di sodium, mono or di potassium salt of carboxylic acids such as acetic acid and the like; most preferably mono or di sodium salt of carboxylic acids.

(9) In another embodiment of the present invention, wherein the said base of step (c) is preferably selected from the group consisting of sodium hydroxide, potassium hydroxide, potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate and the like; most preferably sodium bicarbonate.

(10) In another embodiment of the present invention, wherein the said metal sulfate of step (c) is copper sulfate and the like.

(11) In another embodiment of the present invention, wherein the said solvent of step (c) is preferably selected from the group consisting of heptane, monochlorobenzene (MCB), isoparaffinic hydrocarbon (Isopar-G) and the like or mixture thereof; most preferably heptane or isoparaffinic hydrocarbon.

(12) In another embodiment of the present invention, wherein the said acid of step (d) is either organic or inorganic acid. The said acid is more preferably selected from sulfuric acid, hydrochloric acid, thionyl chloride and the like; most preferably sulfuric acid or thionyl chloride.

(13) In another embodiment of the present invention, wherein the said solvent of step (d) is preferably selected from the group consisting of monochlorobenzene, ethylene dichloride, dichlorobenzene and the like or mixture of solvents thereof.

(14) In another embodiment of the present invention, wherein the said metal halogenate (NaXO.sub.3/KXO.sub.3) of step (e) is preferably selected from the group consisting of sodium bromate (NaBrO.sub.3), sodium chlorate (NaClO.sub.3), sodium iodate (NaIO.sub.3), potassium bromate (KBrO.sub.3), potassium chlorate (KClO.sub.3), potassium iodate (KIO.sub.3), N-bromosuccinimide (NBS) and the like; most preferably sodium bromate.

(15) In another embodiment of the present invention, wherein the said substituent X is selected from the group consisting of chlorine, bromine, iodine.

(16) In another embodiment of the present invention, wherein the said catalyst of step (e) is optionally used, which is preferably selected from the group consisting of sodium bromide (NaBr), potassium bromide (KBr), sodium iodide (NaI), potassium iodide (KI), azobisisobutyronitrile (AIBN) and the like or mixture thereof; most preferably azobisisobutyronitrile.

(17) In another embodiment of the present invention, wherein the said base of step (e) is preferably selected from the group consisting of sodium bisulfite (NaHSO.sub.3), potassium bisulfite (KHSO.sub.3), sodium hydroxide, potassium hydroxide and the like; most preferably sodium bisulfite.

(18) In another embodiment of the present invention, wherein the said solvent of step (e) in combination with water is preferably selected from the group consisting of ethylene dichloride, dichloromethane, chloroform, monochlorobenzene, acetonitrile, diisopropyl ether, ethyl acetate and the like or mixture of solvents thereof; most preferably ethylene dichloride.

(19) In another embodiment of the present invention, wherein the said base of step (f) is preferably selected from the group consisting of sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate and the like; most preferably potassium carbonate.

(20) In another embodiment of the present invention, wherein the said phase transfer catalyst of step (f) is preferably selected from the group consisting of tetra-n-butylammonium bromide (TBAB), tetrabutylammonium iodide (TBAI), tetrabutylammonium chloride (TBACl), sodium iodide, potassium iodide and the like; most preferably tetra-n-butylammonium bromide.

(21) In another embodiment of the present invention, wherein the said solvent of step (f) is preferably selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, xylene, toluene, monochlorobenzene, propionitrile, acetonitrile and the like or mixture of solvents thereof; most preferably acetone.

(22) In another embodiment of the present invention, wherein the crude compound of formula (I) is purified by crystallization in suitable alcoholic solvent which is preferably selected from the group consisting of water, methyl alcohol, ethyl alcohol, isopropyl alcohol and the like or mixture thereof; most preferably isopropyl alcohol.

(23) In another embodiment of the present invention, wherein any one of the steps or all the said steps from (a) to (f) may be performed in in-situ manner.

(24) In another embodiment of the present invention, wherein all the crude compound is preferably used as such or purified by distillation or crystallization or by different purification techniques well understood by those skilled in the art. The preparation of the starting material used in the present invention are well known in prior art.

(25) The invention is further illustrated by the following examples, which should not be construed to limit the scope of the invention in anyway.

EXAMPLES

Example 1: Preparation of (E)-2-methoxyimino-2-(o-tolyl)acetic acid (Compound 5) in One Step

Pot-A

(26) The four neck R. B. flask equipped with mechanical stirrer, thermopocket and water condenser was arranged. The water (3.0 vol. w.r.t. o-toluidine) followed by concentrate hydrochloric acid (3.0 vol. w.r.t. o-toluidine) was charged under stirring and cooled the reaction mass to 0° C. to 5° C. o-Toluidine (1.0 eq.) was added drop wise over 30 min to reaction mass under stirring at 0° C. to 5° C. to form off white slurry. This reaction mixture (RM) was stirred for 30 min. The solution of NaNO.sub.2 (1.0 eq.) in water (1.0 vol. w.r.t. o-toluidine) was added to reaction mixture lot wise over 30 min at −15° C. to 0° C. After complete addition, the solution was used for the next operation.

Pot-B

(27) To the four necks R. B. flask equipped with mechanical stirrer, thermopocket, water condenser and addition funnel the glyoxylic acid (1.5 eq.), methoxyl amine hydrochloride (1.5 eq.) followed by water (4.0 vol. w.r.t.o-toluidine) was charged under stirring to form clear solution and reaction mixture further stirred at 25° C. to 30° C. for 1.0 h. The solution of the sodium carbonate (2.0 eq.) in water (6.0 vol, w.r.t. o-toluidine) was added lot-wise to reaction mass under stirring. The solution of copper sulphate pentahydrate in water was added to reaction mixture under stirring and further heptane or isoparaffinic hydrocarbon (3.2 vol. w.r.t. o-toluidine) was added. Then RM from Pot-A was slowly added to Pot-B over period of 2.0 h maintaining reaction temperature 15° C. to 30° C. The pH was maintained between 6.5 to 5.0 by addition of aqueous Na.sub.2CO.sub.3 solution. The reaction mixture was allowed to stir at 25° C. to 30° C. for 2 hand MDC (10 vol., w.r.t. o-toluidine) was charged and stirred for 15 min. The aqueous and organic layer was separated, extracted the aqueous layer with MDC and combined organic layer was evaporated under vacuum to obtained brown mass (Yield-77% on purity basis, HPLC purity-90%).

(28) .sup.1H NMR (CDCl.sub.3, TMS) δ (ppm): 7.35-7.09 (m, 4H), 4.06 (s, 3H), 2.18 (s, 3H). .sup.13C NMR (CDCl.sub.3, CHCl.sub.3) δ (ppm): 165.4, 149.5, 136.1, 129.9, 129.5, 129.3, 127.9, 129.4, 63.9, 19.4. MS (m/z) (M−1).sup.+=192.

Example 2: Preparation of (E)-2-methoxyimino-2-(o-tolyl)acetic acid (Compound 5) in One Step

Pot-A

(29) To the four neck R. B. flask equipped with mechanical stirrer, thermopocket and water condenser water (3.0 vol. w.r.t. o-toluidine) concentrated hydrochloric acid (3.0 vol. w.r.t. o-toluidine) was charged under stirring, then solution was cooled to 0° C. o-Toluidine (1.0 eq.) was added drop wise over 30 min. to reaction mass under stirring at 0° C. to form off white slurry and further stirred for 30 min. The solution of NaNO.sub.2 (1.0 eq.) in water (1.0 vol. w.r.t. o-toluidine) was added dropwise to reaction mixture over 30 min at −5° C. to 0° C. and after complete addition, the solution was used as such for next operation.

Pot-B

(30) To the four neck R. B. flask equipped with mechanical stirrer, thermopocket, water condenser and addition funnel glyoxylic acid (1.5 eq.), methoxyl amine hydrochloride (1.5 eq.) and water (4.0 vol. w.r.t. o-toluidine) was charged under stirring to form clear solution, the reaction mixture was cooled to 0° C. to 5° C. The NaOH solution (48% solution, 1.3 eq.) was added drop wise to reaction mass under stirring at 5° C. to 10° C. After complete addition of NaOH solution, the reaction mixture was warmed to room temperature and stirred for the 1.0 h. The solid sodium acetate trihydrate (6.0 eq.) was added lot-wise to reaction mixture under stirring and maintained the pH of the between pH 5 to 7. The copper sulphate pentahydrate solution in water (1.0 vol. w.r.t. o-toluidine) was added to reaction mixture under stirring followed by heptane (5 vol. w.r.t. o-toluidine). The reaction mixture from Pot-A was slowly added to Pot-B over period of 2.0 h maintaining reaction temperature at 25° C. to 30° C. and pH between 6.5 to 5.0 by addition of sodium acetate. After complete addition the reaction mixture was allowed to stir at 25° C. to 30° C. for 2 h. The RM was filtered through buchner funnel, the filtrate allowed to settle, and heptane layer was separated. The aqueous layer was extracted with MDC (3×5.0 vol.) and the organic layer is mixed with previously filtered solid and then distilled under reduced pressure to give solid brown mass of Compound 5 (Yield-68% on purity basis, HPLC purity 91%).

Example 3: Preparation of (E)-2-methoxyimino-2-(o-tolyl)acetic acid methyl ester (Compound 6)

(31) To the four neck R.B. Flask with mechanical stirrer, air condenser, thermopocket, water bath the solution of compound 5 (1.0 eq.) in MeOH (3-5 vol. w.r.t. compound 5) was charged. The concentrated H.sub.2SO.sub.4 (0.8 eq.) was added slowly drop wise to reaction mixture at 25° C. to 30° C. over 15 min and heated to reflux temperature for 12 h. The reaction mixture was cooled to 50° C. to 55° C. and water (3.0 vol. w.r.t. compound 5) was added lot wise within 1 h. After complete addition of water, the reaction mixture was stirred for 3 h at 20° C. to 25° C. and filtered on buchner funnel, washed the solid with water and dried the crude product. The crude product was dissolved in isopropyl alcohol (1.43 vol. w.r.t. intermediate 5) and the mixture was heated to 60° C. The solution was cooled the to room temperature, stirred for 1 h and further cooled to −5° C. to 0° C. The solid obtained was filtered on buckner funnel and dried to obtained compound 6 (Yield-80% on purity basis, HPLC purity 97%.) The characterization details of compound (6) is as follows:

(32) .sup.1H NMR (CDCl.sub.3, TMS) δ (ppm): 7.33-7.09 (m, 4H), 4.04 (s, 3H), 3.86 (s, 3H), 2.18 (s, 3H). .sup.13C NMR (CDCl.sub.3, CHCl.sub.3) δ (ppm): 163.5, 150.0, 135.9, 130.2, 129.9, 129.3, 127.8, 125.4, 63.7, 52.9, 19.4. MS (m/z) (M+1).sup.+=208. The same reaction was also performed using methanol and thionyl chloride. The isolated yield of compound (6) was 75% on purity basis, HPLC purity 98%. Similarly, compound (5) is first converted to acid chloride intermediate then treated with methanol to yield compound (6) in 86% yield, HPLC purity 94%.

Example 4: Preparation of (E)-2-(2-bromomethylphenyl)-2-methoxy iminoacetic acid methyl ester (compound 7)

(33) To the four neck R.B. Flask with mechanical stirrer, water condenser, thermopocket and oil bath EDC (5.0 vol. w.r.t. compound 6) and compound (6) in 1.0 eq was charged to under stirring at 25° C. to 30° C. to obtain clear solution. The water (3.0 vol. w.r.t. compound 6) was charged into reaction mixture and stirred for 30 min. The NaBrO.sub.3 (1.25 eq.) was added slowly to the reaction mixture under stirring to obtain a clear biphasic solution and further cooled to 5° C. to 10° C. The solution of sodium bisulphite (2.0 eq.) in water (2.0 vol. w.r.t. compound 6) was added to reaction mass slowly drop-wise using addition funnel, maintaining reaction temperature at 5° C. to 10° C. for over 1 h. After complete addition, the reaction mixture was allowed to warm to 20° C. to 25° C. and further heated to 70° C. to 75° C. The reaction mass was cooled to 20° C. to 25° C., separated the organic layers and solvent was removed under vacuum to give crude compound (7). The crude-compound was recrystallized using IPA (Yield-77% on purity basis, HPLC purity 97%). The characterization details of compound (7) is as follows:

(34) .sup.1H NMR (CDCl.sub.3, TMS) δ (ppm): 7.49-7.34 (m, 3H), 7.15-7.13 (m, 1H), 4.32 (s, 2H), 4.06 (s, 3H), 3.87 (s, 3H). .sup.13C NMR (CDCl.sub.3, CHCl.sub.3) δ (ppm): 162.6, 148.5, 135.3, 130.0, 129.7, 129.4, 128.3, 128.0, 63.4, 52.6, 30.5. MS (m/z) (M).sup.+=286.

(35) The same reaction was also performed in presence of catalyst azobisisobutyronitrile which completed in one hour (Yield-70% on purity basis, HPLC purity 97%).

Example 5: Preparation of Trifloxystrobin Formula (I)

(36) To the four neck R.B. Flask with mechanical stirrer, water condenser, thermopocket and nitrogen inlet the compound 7 (1.0 eq.), compound 8 (1.05 eq.), acetone (3.0 vol. w.r.t. compound 7), TBAB (0.05 eq.), K.sub.2CO.sub.3 (2.5 eq.) were charged under stirring at 25° C. to 30° C. The reaction mixture was stirred at 25° C. to 30° C. for 24 h and filtered through celite bed, washed the celite bed with acetone (3.0 vol. w.r.t. compound 7). The combined organic layer was distilled under vacuum (15 to 20 Torr) at 40° C. to 45° C. to give crude compound. The crude compound was recrystallized using IPA (Yield-88% on purity basis, HPLC purity 99%). The characterization details of compound (I) is as follows:

(37) .sup.1H NMR (CDCl.sub.3, TMS) δ (ppm): 7.86 (bs, 1H), 7.79-7.77 (m, 1H), 7.59-7.57 (m, 1H), 7.50-7.36 (m, 4H), 7.20-7.18 (m, 1H), 5.14 (s, 2H), 4.02 (s, 3H), 3.81 (s, 3H), 2.21 (s, 3H). .sup.13C NMR (CDCl.sub.3, CHCl.sub.3) δ (ppm): 163.0, 153.3, 149.3, 136.9, 135.8, 130.4, 129.7, 129.1, 129.0, 128.6, 128.5, 128.3, 127.5, 125.3, 123.8, 122.5, 74.7, 63.4, 52.4, 12.1. MS (m/z) (M+1).sup.+=409.

(38) The same reaction was also performed at higher temperature (40° C. to 45° C.) and the reaction was completed in 4 to 6 hours. The reaction was also performed in acetonitrile or propionitrile and isolated yield of the compound in formula (I) was increased to 90%, HPLC purity 98.7%.

Abbreviations

(39) AIBN: Azobisisobutyronitrile CH.sub.3COONa: Sodium acetate CuSO.sub.4: Copper (II) sulphate DIPE: Diisopropyl ether DMA: Dimethyl acetamide DMF: Dimethyl formamide EDC: Ethylene dichloride Eq.: Equivalent g: Gram h: Hours H.sub.2O: Water H.sub.2SO.sub.4: Sulfuric acid HCl: Hydrochloric acid HCN: Hydrogen cyanide HPLC: High performance liquid chromatography IPA: Isopropyl alcohol Isopar-G Isoparaffinic Hydrocarbon KBr: Potassium bromide KBrO.sub.3: Potassium bromate KClO.sub.3: Potassium chlorate KCN: Potassium cyanide K.sub.2CO.sub.3: Potassium carbonate Kg: Kilogram KHCO.sub.3: Potassium bicarbonate KHSO.sub.3: Potassium bisulfite KI: Potassium iodide KIO.sub.3: Potassium iodate KNO.sub.2: Potassium nitrite KOH: Potassium hydroxide K.sub.2SO.sub.3: Potassium sulfite L: Litre MCB: Monochlorobenzene MDC: Methylene dichloride MeOH: Methanol MeONH.sub.2.HCl: Methoxylamine hydrochloride MIBK: Methyl isobutyl ketone mL: Millilitre NaBr: Sodium bromide NaBrO.sub.3: Sodium bromate NaClO.sub.3: Sodium chlorate NaCN: Sodium cyanide Na.sub.2CO.sub.3: Sodium carbonate NaHCO.sub.3: Sodium bicarbonate NaHSO.sub.3: Sodium bisulfite NaI: Sodium iodide NaIO.sub.3: Sodium iodate NaNO.sub.2: Sodium nitrite NaOBr: Sodium hypobromide NaOH: Sodium hydroxide NBS: N-bromo succinamide PTC: Phase transfer catalyst R.B. Flask: Round bottom flask RM: Reaction mixture rt: Room temperature SOCl.sub.2: Thionyl chloride TBAB: Tetra n-butyl ammonium bromide TBACl: Tetrabutylammonium chloride TBAI: Tetrabutylammonium iodide Vol: Volume

Advantages of the Present Invention

(40) 1. The intermediate (E)-2-methoxyimino-2-(o-tolyl)acetic acid (compound 5) is synthesised in a single step, as compared to prior art process, which has more number of steps. 2. The key raw material of the instant invention such as o-toluidine is common starting material and easily available in large scale at commercial level. 3. In instant invention (E)-2-methoxyimino-2-(o-tolyl)acetic acid is obtained directly in an (E)-isomeric form and it is essential for further conversion into trifloxystrobin, while comparing to other literature processes the present invention is distinct and advantageous. 4. In instant invention trifloxystrobin is produced using lesser number of steps with 40.2% overall yield, while the literature reports many step syntheses with overall yield 19%. 5. The instant invention does not require the use of any hazardous cyanide reagent; therefore, the said process is environment friendly and safe. 6. In literature step (f) was performed at higher temperature about 120° C. using polar high boiling solvents such as DMF, DMA which are difficult to separate from trifloxystrobin. The high temperature reaction causes impurity formations, which results in lower yield (about 65%) of trifloxystrobin. However, the present invention was performed by using low boiling solvents such as acetone at room temperature (20° C. to 30° C.) to produce trifloxystrobin (88% yield). 7. The instant invention produces trifloxystrobin in a high yield (90%) with high chemical purity (98-99.5%).