Two novel substituted phenyl isoxazole benzoxazine formamide derivatives were designed and synthesized with substituted
o-aminophenol, 1,2-dibromoethane and different phenyl substituted
isoxazole formyl chloride as the raw materials
via microwave assistant synthesis. The target compounds were characterized by IR,
1H NMR,
13C
NMR and HRMS. Both single-crystal structures were further determined by X-ray diffraction. 3-(2΄-Chloro-6΄-fluoro-phenyl)-4-(2΄,3΄-dihydro-1΄,4΄-benzoxazine)-5-methyl-isoxazole formamide (
4a) crystallizes in
orthorhombic system,
P2
1 space group with
a = 8.9414(18),
b = 10.834(2),
c = 17.706(4) Å,
V =
1715.1(6) Å
3,
Dc = 1.444 Mg/m
3,
Z = 4,
F(000) = 768,
m(Mo
Ka) = 0.255 mm
-1,
R = 0.0406 and
wR =
0.1171. 3-Phenyl-4-(6- methyl-2΄,3΄-dihydro-1΄,4΄-benzoxazine)-5-methyl-isoxazole
formamide (
4b) is of triclinic system, space group
P
with
a = 7.7659(16),
b = 8.3626(17),
c =
13.484(3) Å,
a = 76.04(3)°,
b = 100.63(3)°,
g = 82.01(3)°,
V = 841.6(3) Å
3,
Dc = 1.319 Mg/m
3,
Z = 2,
F(000) = 352,
m(Mo
Ka) = 0.090 mm
-1,
R = 0.0672 and
wR =
0.2671. Both crystals are packed through C–H···O hydrogen bonding interaction. There
is C–H···F hydrogen bond between
4a molecules, and C–H···N between
4b molecules. Bioassay results showed
that compounds
4a and
4b exhibited detoxification on maize
and restored maize growth index.