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276

Pesticides

Synthesis

Handbook

Glyphosate
Uses:

herbicide, coffee, tea, bananas, cotton, soyabeans, fruit Round-up (Monsanto)

rubber, coconut,

cocoa, cereals,

Trade names:

Type:

phosphonate

Synthesis: / Cl P--C1 \ C1 phosphorus trichloride CI \ i o=- P-- ~-- CI / ' C1 formaldehyde

--c /

>

H20

OH

I
o~P--

//o XN-OH

OH
I j '

c - - N-- c--c

I
OH

'

--c

\
Ott

o== P-- c-- CI


I

chloromethyl pho sphonic acid

OH

glyphosate

glycine

alternate routes

:
I C~ I C-,-

O~

i)

~N-- 0c--c i \ , ,
O-'-C--C---.

/
--C

HO-- P \

J
O D C ~ C

J
--

diethyl phosphite

I formaldehyde
or

ethyl glycinate
or

glycine

OH / o ~ P --OH \ H

phosphorous acid

OH o=P--

' ,=_
' ~

N-- c-- c

//

OH

l
0

'

HCI
OH

o=P-I I ,

N-l \

c
I i I I

I
OH

'

OH

o-- c-- c--

glyphosate

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