Method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds

Details Method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds Method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds

1979-04-25

1980-09-23

Trousof, Natalie

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260564B, C07C12916

Patent

active

042242452

ABSTRACT:
The present invention provides an improved method of making 1-(alkoxyphenyl)-5-(phenyl)biguanide compounds which are useful as agricultural fungicides, having the formula: ##STR1## where R is alkyl, linear of branched, having from 1-14 carbon atoms; and acid addition salts thereof.
The method comprises the steps of (a) alkylating a nitrophenol with a suitable alkyl halide in a reaction solvent to form an alkoxynitrobenzene intermediate, (b) reducing the nitro group of the itermediate in situ by catalytic hydrogenation to form an alkoxyaniline, and (c) condensing the alkoxyaniline with phenyldicyandiamide to form the desired biguanide as the acid addition salt.
The invention also includes a novel isolation and purification procedure for obtaining purified biguanide acid addition salts and purified free biguanide base.

REFERENCES:
patent: 2704710 (1955-03-01), Sprung
patent: 3222398 (1965-12-01), Brown et al.
patent: 4137332 (1979-01-01), Brown et al.
Wheeler, Henry L. et al., J. Am. Chem. Soc., vol. 25, pp. 719-722 (1903).

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