OPTICALLY ACTIVE 1,2-DISUBSTITUTED-2,3-EPOXYPROPANES, THEIR PRODUCTION AND INTERMEDIATE AND HERBICIDE COMPRISING THE SAME AS ACTIVE INGREDIENT

摘要

PROBLEM TO BE SOLVED: To obtain optically active new compounds having a high herbicidal activity in a small dose. SOLUTION: The optically active 1,2-disubstituted-2,3-epoxypropanes are represented by formula I [A is a group represented by formula II (R1 is H, a lower alkyl or the like; Q is a halogen, a 1-3C alkyl or the like; n is an integer of 0-4) or a group represented by the formula: CX13(CX22)p (X1 and X2 are each a halogen or H; p is 0-2); B is a (substituted)aryl], e.g. (-)-2-[2-(3- chlorophenyl)-2,3-epoxypropyl]-2-ethylindan-1,3-dione. The compounds represented by formula I are obtained by reacting, e.g. a compound represented by formula III (Ra is HO; Rb is OH) with a sulfonic acid derivative such as methanesulfonyl chloride in the presence of a base such as pyridine, providing optically active sulfonic esters represented by formula III (Ra is OH; Rb is OSO2CH3) and then cyclizing the resultant optically active sulfonic esters in the presence of a base such as potassium carbonate.