Hexaconazole is a triazole fungicide used on vines, coffee, and peanuts. It is sold under the trade name Anvil. It can be synthesized via two routes, one starting with m-dichlorobenzene and another starting with chloroacetyl chloride. Both routes involve multiple steps of reactions with reagents like pentyl chloride, dimethyl sulfide, and methyl iodide to ultimately form the 1,2,4-triazole core structure and add chlorine and alkyl groups to produce hexaconazole.

1. 706 Pesticides Synthesis Handbook
Hexaconazole
Uses: fungicide, vines, coffee, peanuts
Trade names: Anvil (ICl)
Type : triazole
Synthe sis :
~ CI
CI
m.dichloro
benzene
o
,,~_, //--' C--- C--- C---C
i i i
Cl
pentyl chloride
I I
-?-s-?-
dimethyl
sulfide
-I-I
methyl
iodide
I
-- ~:-- S-- c--
I t H202
hydrogen
peroxide
)
o
II , t I i
c-- r
I J I Ii
C1
I
-?
--~--S-- I
I
trimethyl
sulfonium
iodide
o
, ISI cI-- dimethyl"" C--- I.
I ! sulfoxide
o
_/,
I I
I ~ C I
CI
Na
I
1.2.4 triazole
soldium salt
OH
C----C----C--C----C--
/ I I I
# ,
C1
CI
hexaconazole

2. alternate route:
~ CI
C1
hexaconazole ."
o
I
Cl
chloro
acetyl
chloride
I
/N
N
Heterocyclic Nitrogen Compounds
o
CI
Ci
I I I I
--c--c-- -- -- Li
, , ~
n.butyl
lithium
OH
Cl . . . . c-- -- c--
C1
C1
707