MY141190A - A process for the large scale manufacture of indoxacarb and associated 1, 3, 4 oxadiazines - Google Patents

Abstract

THIS INVENTION RELATES TO AN IMPROVED METHOD FOR THE N- CARBOMETHOXYLATION OF THE 1,3,4 OXADIAZINES OF FORMULA (11), AND PARTICULARLY INDOXACARB, USING METHYL CHLBRO FQRMATE IN THE PREOENCE OF NODIUM HYDRIDE RESULTING IN 10 COMPOUNDS OF FORMULA (1) IN WHICH THE RATIO OF THE ACTIVE S-ISOMER TO THE INACTIVE R-ISOMER IN THE PRECURSOR CAN BE RETAINED. RATIOS GREATER THAN OR EQUAL TO 751 S-ISOMER, PREFERABLY GREATER THAN OR EQUAL TO 99, ARE ACHIEVABLE IN THE LARGE SCALE MANUFACTURING OF THE AXADIAZINES OF FORMULA (1) IN THIS PROCESS. WHEREIN RI = F, CL OR C1-C3 FLUROALKOXY, R2 = C1-C3 LINEAR OR BRANCHED ALKYL, OR UNSUBSTITUTED OR HETERO SUB3TITUTED ARYL, 25 R3 @ CI-C3 LINEAR OR BRANCHED ALKYL, AND R4 = TRIFLUROMETHOXY, TRIELUROMETHYL, F, CL OR BR. THE INVENTION PARTICULARLY RELATES TO A PROCESS FOR THE CONVERSION OF THE COMPOUND OF FORMU.LA (II) TO THE COMPOUND OF FORMULA (I) WHEREIN RL = CL, R2 = CH3, R3 = CH3 AND R4 = OCF3, I.E. A PROCESS FOR THE PRODUCTION OF INDOXACARB. THE INVENTION PARTICULARLY RELATES TO A PROCESS FOR THE CONVERSION OF THE COMPOUND OF FORMU.LA (II) TO THE COMPOUND OF FORMULA (I) WHEREIN RL = CL, R2 = CH3, R3 = CH3 AND R4 = OCF3, I.E. A PROCESS FOR THE PRODUCTION OF INDOXACARB. THE INVENTION PARTICULARLY RELATES TO A PROCESS FOR THE CONVERSION OF THE COMPOUND OF FORMU.LA (II) TO THE COMPOUND OF FORMULA (I) WHEREIN RL = CL, R2 = CH3, R3 = CH3 AND R4 = OCF3, I.E. A PROCESS FOR THE PRODUCTION OF INDOXACARB. THE INVENTION PARTICULARLY RELATES TO A PROCESS FOR THE CONVERSION OF THE COMPOUND OF FORMU.LA (II) TO THE COMPOUND OF FORMULA (I) WHEREIN RL = CL, R2 = CH3, R3 = CH3 AND R4 = OCF3, I.E. A PROCESS FOR THE PRODUCTION OF INDOXACARB. THE INVENTION PARTICULARLY RELATES TO A PROCESS FOR THE CONVERSION OF THE COMPOUND OF FORMU.LA (II) TO THE COMPOUND OF FORMULA (I) WHEREIN RL = CL, R2 = CH3, R3 = CH3 AND R4 = OCF3, I.E. A PROCESS FOR THE PRODUCTION OF INDOXACARB.