1. Hctcrocyclic Nitrogen Compounds 597
Propaquizafop
Uses: herbicide, cotton, peanuts, potatoes, soyabeans, sugar beet, vegetables
Trade names: Agil, Shogun (Ciba)
Type: quinoxaline
S~j-nthesis :
I I I I
-- c-- c-- c-- + HCl .~N---OH > -- c---c--c-- acetone
I II I I II I oxime
o N--OH
acetone
hydroxylamine
hydrochloride
I I
----- C---C----C----
I N I
N
I
0
I
--C--
I
--C-- 0
I l
0 C----C'---C--
I I
OH
O
= = //
-,,- C'-." C'--'-C
I I
OH OH
lactic acid
(calcium lactate)
I I
-- c-.-----c-- ethylene
/ oxide
0
1I I I
---- C-.--C--C----
I I I
N
I
0
I
--C-"
I
--C-"
I
--C--
0~'-~-" S=o
I
OH
t
I I
I U I
N
I
0
I
I
-C-- 0
I g a
0 - C'---C----C-'--
I I
0
I
o==S== 0
I
toluene
sulfonic acid
l
2.6 dichloro
quinoxal ine
OH
hydroquinone
OH
i
f

2. 598 Pcsticidcs Synthcsis Handbook
0
. _
' I o-~-~'- + Hc~
o I I
0
I
~C~
I
I I
"- C'--"C----C'--
I II I
N
I
0
I
-~-
--C-- 0
I I n
0 " C--'- C"- C"-"
I I
0
0
I
I
H20
I I
~C'==-C "---C'--
i II l
N
I
0
I
I
--C-- 0
I % I i
O- C-" C'-- C---
I '
0
I
OH
O
--" C"---C--C
I " Oil
0
O
I
m c --
I
thionyl
SOC12 chloride
O
I i n 0 #
-- c--c--c-- + --c---c---c
I II I I I
N I CI
I o
O
I
-e-
l
-e-
l
OH
O
I
mCm
I
> propaquizafop
2.6 dichloro
quinoxal ine

3. Heterocyclic Nitrogen Compounds 599
I I
--'- C----C----C----
I II I
N
I
o
I
--C--
I
--C-- O
I ~ I
o C---- C---C---
I l
O
CI
propaquizafop
alternate route:
o
, //
----C---C--C
OH o--c-- c--
I I
o==S-----o
I
OH
0
l #
. ----C--C--C
I i j
O O--C--C--
I I I
o----S----O
--C-
I
OH
0
I ,
--C--C--"
I I
monoe thyl
ether of
hydroquinone
0
I dime thy I
--C// C--
/I formamide
N'
k,