Patent GB-745168-A (GB)
Title: Improvements in or relating to the preservation of material from attack by micro-organisms such as fungi, yeasts, bacteria and protozoa
IPC: A01N43/78
Filed: 1953-06-16
Abstract: Compounds of formula <FORM:0745168/IV(a)/1> wherein R1 is an aromatic radical directly linked to the N-atom and substituted by one or more polar groups (including halogens) preferably having double or triple bonds (e.g. nitro, hydroxy, alkoxy, acetyl, carboxyl or carboalkoxy groups) and wherein Z represents the group <FORM:0745168/IV(a)/2> or <FORM:0745168/IV(a)/3> in which R2 and R3 are hydrogen or substituted or non-substituted aliphatic or aromatic groups, are prepared (1) by reacting "polar" substituted phenylisothiocyanates with thioglycollic acid or esters thereof; (2) by reacting a "polar" substituted aromatic primary amine with carbon disulphide and caustic alkali to give the corresponding dithiocarbamates which are subsequently reacted with monochloracetic acid; (3) by reacting a "polar" substituted aromatic primary amine with the reaction product from a trithiocarbonate and a substituted or unsubstituted monochloracetic acid; (4) by condensing N-substituted rhodanines (prepared as in (1) to (3)) with aldehydes in presence of concentrated sulphuric acid. The following are prepared or described: paraphenylene - N,N1 - bis - rhodanine; N - paranitrophenyl, N-21,41-dinitrophenyl-, N-parachlorophenyl-, N-21,41-dichlorophenyl-, N-21-chloro-41-nitrophenyl-, N-para-acetophenyl-, N-para - carbethoxyphenyl-, N - para - methoxyphenyl-, 3-para-chlorophenyl-5-propyl-, 3-paranitrophenyl-5-carboxymethyl-, and 3-paranitrophenyl-5-benzylidene-rhodanine.  Ammonium para - phenylene - bis - dithiocarbamate is prepared by reacting para-phenylene with carbon disulphide and aqueous ammonia.ALSO:Stored seeds, seed bulbs and seed tubers are preserved from attack by fungi, yeasts, bacteria, protozoa and like micro-organisms by contacting (e.g. by dusting, spraying or coating) with an agent which comprises one or more compounds of formula <FORM:0745168/I/1> wherein Z represents the group <FORM:0745168/I/2> in which both R2 and R3 represent a hydrogen atom or a substituted or unsubstituted aliphatic or aromatic radical, dispersed or dissolved in (1) an inert finely-divided solid carrier (e.g. talcum, bentonite), R1 being defined here as an aromatic radical linked directly to the nitrogen atom and substituted by one or more polar groups which are preferably halogens, hydroxy or alkoxy groups, or groups containing a double or triple bond and two or more of the elements N, C, O and H (e.g. nitro, acetyl, carboxyl and carboxylic groups); or (2) an inert solvent, R1 being defined here as an aromatic radical linked directly to the nitrogen atom and substituted by one or more polar groups consisting of halogens, hydroxy or alkoxy groups, or groups containing at least one nitrogen-oxygen or carbon-oxygen double bond. Active ingredients include N,N1 - (paraphenylene) - bis - rhodanine, while adherents and dispersing agents such as sulphonates are optional additives.ALSO:An agent for preserving timber, leather, textile material, stored seeds, seed bulbs or seed tubers from attack by fungi, yeast, bacteria, protozoa and like micro-organisms comprises one or more compounds of formula <FORM:0745168/VI/1> wherein Z represents the group <FORM:0745168/VI/2> in which both R2 and R3 represent a hydrogen atom or a substituted or unsubstituted aliphatic or aromatic radical, dispersed or dissolved in (1) an inert finely-divided solid carrier, R1 being defined here as an aromatic radical linked directly to the nitrogen atom and substituted by one or more polar groups which are preferably halogens, hydroxy or alkoxy groups, or groups containing a double or triple bond and two or more of the elements N, C, O and H (e.g. nitro, acetyl, carboxyl and carbalkoxy groups); or (2) an inert solvent, R1 being defined here as an aromatic radical linked directly to the nitrogen atom and substituted by one or more polar groups consisting of halogens, hydroxy or alkoxy groups, or groups containing at least one nitrogen-oxygen or carbon-oxygen double bond.  Active ingredients include N, N1-(paraphenylene)-bis-rhodanine and inert diluents are, for example, talcum and bentonite.  Adherents and dispersing agents such as sulphonates may also be added.