2,2'-OXO-1,1'-AZOBENZENE - A MICROBIALLY TRANSFORMED ALLELOCHEMICAL FROM 2,3-BENZOXAZOLINONE .1.

2,2′-Oxo-1,1 ′-azobenzene (AZOB), a compound with strong herbicidal activity, was isolated and characterized from a soil supplemented with 2,3-benzoxazolinone (BOA). A parallel experiment with 6-methoxy-2,3-benzoxazolinone (MBOA) yielded AZOB as well as its mono-(MAZOB) and dimethoxy-(DIMAZOB) derivatives. These compounds were produced only in the presence of soil microorganisms, via possible intermediates, I and II, which may dimerize or react with the parent molecule to form the final products. In the case of MBOA, it was shown that demethoxylation precedes the oxidation step. Although BOA and 2,4-dihydroxy-1,4(2H)-benzoxazin-3-one (DIBOA) were leached out of rye residues, there were no detectable amounts of the biotransformation products in the soil. When BOA was mixed with soil and rye residue, either under field conditions or in vitro, AZOB was detected. Levels of free BOA in the soil were greatly reduced by incubation with rye residue. AZOB was more toxic to curly cress (Lepidium sativum L.) and barnyardgrass (Echinochloa crusgatti L.) than either DIBOA or BOA. © 1990 Plenum Publishing Corporation.