Carboxin is a fungicide used on cereals, maize, cotton, peanuts and soybeans. It is an oxathiin amide compound synthesized from ethyl acetate, sulfuryl chloride, aniline, and sodium hydroxide or alternatively from ethyl acetate, sulfuryl chloride, and thionyl chloride. Carboxin kills fungi through inhibition of respiration.

1. Heterocyclic Sulfur Compounds 737
Carboxin
Uses : fungicide, cereals, maize, cotton, peanuts, soyabeans
Trade names: Vitavax (Uniroyal)
Type : oxathiin, amide
Synthes is :
I
---- C ~ C ..~.. C--.
0...,--. C~ 0
I
N
O
II i i
/ c----c----c~ c--
N !II t
o aceto
acetanilide
diketene aniline
sulfuryl
S02C12 chloride
O
II t i
c---c------c---c---
N/ I II t
o
I--e-
l
I
Ott
KOH
~0-~-~'-~I I
me rcap to
ethanol
0
II I t
C - - C - - C - - C - -
N/ I Ii f
C1 o
NaOHI /~
-C-
I
,~ //
C C O
/x
C
/
carboxin

2. 738 Pesticides Synthesis Handbook
alternate route :
o
I I fl
--C--C--C--C
I II I I i
0 O--C--C--
I I
O
+ S02C12-----@ --c--c--c--c +
o I o--c--c-
w I
ethyl aceto sul furyl
acetate chloride
Ho--cl--cI-c'SH
I I
KOH
0
s I //
--C--C--C--C
0 O--C--C--
I i
I-c-
--C--
tOH
I
-C-
I
o% ~=
C--C 0
/
S c~
/
c
/
SOCI 2
thionyl
chloride
NaOH
I
-e-
l
O C
~-=//o/
.o I I
C
/
/
N
aniline
I
-e-
l
O
,,/,U
/
carboxin