Co
mpounds with a (2
H)-1,4-benzoxazin-3(4
H)-one skeleton have attra
cted the attention of phyto
che
mistry resear
chers sin
ce 2,4-dihydroxy-(2
H)-1,4-benzoxazin-3(4
H)-one (DIBOA) and 2,4-dihydroxy-7-
methoxy-(2
H)-1,4-benzoxazin-3(4
H)-one (DIMBOA) were isolated fro
m plants bel
onging to thePoa
ceae fa
mily. These
co
mpounds exhibit interesting biologi
cal properties, su
ch as phytotoxi
c,anti
mi
crobial, antifeedant, antifungal, and inse
cti
cidal properties. These
che
mi
cals, in addition to awide variety of related
co
mpounds involved in their
metabolis
m, detoxifi
cation
me
chanis
ms, anddegradation on
crop soils and other syste
ms, have high interest and in so
me
cases potential agrono
mi
cutility. This paper presents a
co
mplete review of the
methods e
mployed for their syntheti
c obtentionin addition to so
me of the authors' own
contributions to their
che
mistry. The degradation andphytotoxi
city experi
ments
carried out in
ongoing resear
ch into the potential agrono
mi
c utility of these
co
mpounds required large a
mounts of the
m, whi
ch were obtained fro
m natural sour
ces. This paperpresents a
modified
methodology to a
ccess DIMBOA fro
m Zea mays cv. Apa
che and to obtain 2-
O-
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D-glu
copyranosyl-2,4-dihydroxy-(2
H)-1,4-benzoxazin-3(4
H)-one (DIBOA-Gl
c) and DIBOA fro
mSecale cereale L. New syntheti
c methodologies were e
mployed for the obtention of the la
cta
ms2-hydroxy-(2
H)-1,4-benzoxazin-3(4
H)-one and 2-hydroxy-7-
methoxy-(2
H)-1,4-benzoxazin-3(4
H)-oneand the
malona
mi
c a
cids
N-(2-hydroxyphenyl)
malona
mi
c a
cid and
N-(2-hydroxy-7-
methoxyphenyl)
malona
mi
c a
cid. The a
minophenoxazines 2-a
mino-7-
methoxyphenoxazin-3-one and 2-a
ceta
mido-7-
methoxyphenoxazin-3-one have been synthesized in the authors' laboratory by novel pro
cedures.All of the
methodologies e
mployed allowed the desired
co
mpounds to be obtained in high yield andin an easy-to-s
cale
manner.Keywords: Allelo
che
mi
cals; DIMBOA; DIBOA; soil degradation produ
cts; wheat; isolation; synthesis;preparation