Soil transformation of wheat and corn metabolites mboa and DIM2BOA into aminophenoxazinones

P Kumar; R W Gagliardo; W S Chilton

doi:10.1007/BF00980682

Soil transformation of wheat and corn metabolites mboa and DIM2BOA into aminophenoxazinones

J Chem Ecol. 1993 Nov;19(11):2453-61. doi: 10.1007/BF00980682.

Authors

P Kumar¹, R W Gagliardo, W S Chilton

Affiliation

¹ Department of Botany, North Carolina State University, Box 7612, 27695-7612, Raleigh, North Carolina.

PMID: 24248702
DOI: 10.1007/BF00980682

Abstract

The defensive cyclic hydroxamates 7-methoxy-2,4-dihydroxy-1,4(2H)-benzoxazin-3-one (DIMBOA) and 7,8-dimethoxy-2,4-dihydroxy-1,4(2H)-benzoxazin-3-one (DIM2BOA) of wheat and corn are transformed in nonsterile soil, via 6-methoxy-2(3H)-benzoxazolone (MBOA) and 6,7-dimethoxy-2(3H)-benzoxazolone (M2BOA) respectively, into 2-amino-7-methoxy-3H-phenoxazin-3-one and 2-amino-4,6,7-trimethoxy-3H-phenoxazin-3-one. The soil transformation is similar of that undergone by the rye metabolite 2(3H)-benzoxazolone (BOA) into 2-amino-3H-phenoxazin-3-one. The transformations to phenoxazinones are not observed in sterile soil. The 2-amino-3H-phenoxazin-3-one inhibits barnyard grass radicle elongation, but the methoxylated aminophenoxazinones are not significantly inhibitory.