THE REDUCTION OF 2,4-DIHYDROXY-7-METHOXY-1,4-BENZOXAZIN-3-ONE BY THIOLS

Article abstract of DOI:10.1016/0031-9422(85)80036-4

2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), a naturally occurring hydroxamic acid involved in pest resistance of cereals, was reduced by thiols to the corresponding lactam.Kinetic studies showed that the reactive species are undissociated DIMBOA and thiolate anion.Possible mechanisms for the reaction are discussed in the light of relative reactivities of DIMBOA and a compound lacking the 7-methoxy substituent, and results from molecular orbital calculations.Key Word Index - Zea mays; Gramineae; 1,4-benzoxazin-3-one; thiols; reduction.