Acifluorfen

904

Pesticides Synthesis Handbook

Acifluorfen

Uses:

herbicide, peanuts, rice, soyabeans

Trade n~mp..~: Type :

Tackle (Rhone Poulenc), Blazer (Basf)

phenyl ether

Synthesis:

o\~ /OH D

I c --

C

+

HNO 3

3 hydroxy 6 nitro benzoic acid

02N ~ O H

>

~ O H m-cresol F I F-c-F

F I

F-c-F +

Cl 2

9

3,4 dichloro trifluoro methyl benzene

CI

C1

F

I

=, F

o /OH

o oNa ~\/

.___CI

(

F-~F

NaOH

~

-o

N02

acifluorfen

alternate routes : F I

CN

CN + HNO 3

H2SO4

F-c-F

F

Cl

F-~

)

CI

~ F

-o

CN N0 2

F

OK 3 f luorophenyl cyanide I H3CooH HBr o~/oNa

~

C1

CI

-e NaOH

F

"~"

F - ! ~ o

o~ / OH c

Diverse Chemical Functions

preparation of

o

3 hydroxy 6 nitrobenzoic acid

OH

XXC,/ C]~

No2

+

Cu (OH)

3 chloro 6 nitro benzoic acid (see bifenox)

alternate route:

F HO

.o

o

I

F--c--F

F

%/

CI

. y

Cl Cl

I

_

F

3 hydroxy benzoic acid HNO 3

Cu(OH) 2

i acifluorfen

o

\\/

OH

c

(~C1 3 chloro benzoic acid

OH

905