Patent GB-1103391-A (GB)
Title: (halogeno-cyano) acetyl derivatives and pesticidal preparations containing them
IPC: C07D295/185
Filed: 1965-08-02
Abstract: Washing or cleaning agents comprise bactericidal compounds of the general formula <FORM:1103391/C4-C5/1> where X1 represents a hydrogen or a halogen atom, X2 represents a halogen atom, and Y stands for the residue -OR (in which R represents an alkyl or chloralkyl radical containing up to 18 carbon atoms), or for the residue <FORM:1103391/C4-C5/2> in which R1 and R2 are identical or different and each represents a hydrogen atom or an alkyl, alkoxyalkyl dialkylaminoalkyl, cyclohexyl residue containing up to 18 carbon atoms, or a phenyl radical or the residue of the formula <FORM:1103391/C4-C5/3> or form together with the nitrogen atom, a morpholine, piperidine or piperaxine ring which latter may be substituted by the residue <FORM:1103391/C4-C5/4> incorporated in wash-active compounds such as soaps, alkylarylsulphonates, fatty alcohol sulphates, condensation products from fatty acids and methyl-taurine, condensation products from fatty acids and hydroxy-ethanesulphonates, fatty acid + albumen condensation products, alkylsulphonates, non-ionic products for example, condensation products from alkylphenols with ethylene oxides, as well as cationic compounds.  The active ingredients may also be used in industrial detergents, for example in conjunction with a condensed phosphate, for example, 20 to 50% of alkali metal tripolyphosphate, or in the presence of an organic lyophilic polymer capable of increasing the dirt carrying capacity of the washing liquor, for example, an alkali metal salt of carboxymethylcellulose.ALSO:The invention comprises compounds of the general formula <FORM:1103391/C2/1> where X1 represents a hydrogen or halogen atom: X2 represents a halogen atom, and Y represents the residue -NR1R2 in which R1 and R2 are identical or different and each represents a residue containing up to 12 preferably up to 4 carbon atoms, or an alkyl, alkoxyalkyl, dialkylaminoalkyl, cyclohexyl radical or a phenyl radical or the residue of the formula <FORM:1103391/C2/2> or, together with the nitrogen atom, form a morpholine, piperidine or piperazine ring which latter is substituted by the residue -CO-Cl2-CN Compounds claimed per se are N-methyl and N-ethyl 2,2-dichloro-cyanoacetamide: 2-chlorocyanoacetic acid anilide; and 2,2-dichlorocyano acetic acid piperidide.  Many examples are given. The compounds may be prepared by reacting N-substituted amides of cyano acetic acid (obtained by reacting lower alkyl esters of cyano acetic acid and the corresponding amine) with a halogenating agent e.g. free halogen or sulphuryl chloride in the presence of a catalyst.  In an example N-(n-butyl)-2,2-dichloro-cyanoacetamid is prepared by reacting cyanoacetic acid methyl ester with n-butylamine and allowed to crystallize out when sulphuryl chloride is added.ALSO:Pesticidal fungicidal and bactericidal compositions comprise as active ingredient a compound of the general formula: <FORM:1103391/A5-A6/1> where X1 represents a hydrogen or a halogen atom, X2 represents a halogen atom, and Y stands for the residue -OR (in which R represents an alkyl or chloralkyl radical containing up to 18 C. atoms), or for the residue <FORM:1103391/A5-A6/2> in which R1 and R2 are identical or different and each represents a hydrogen atom or an alkyl, alkoxyalkyl, dialkylaminoalkyl, cyclohexyl residue containing up to 18 C. atoms, or a phenyl radical or the residue of the formula <FORM:1103391/A5-A6/3> or form, together with the nitrogen atom, a morpholine, piperidine or piperazine ring which latter may be substituted by the residue -CO-CCl2-CN, together with a suitable carrier.  Many active ingredients are specified particularly in which X1 and X2 are Cl, Y is -NR1R2 and R1 is H and R2 is H or lower alkyl, phenyl, or R1, R2 together form a piperidyl radical. The compositions may be used as disinfectants and for protecting paper, timber; and fibrous and textile materials against harmful organisms.  The active ingredients may be incorporated in skin cleaning preparations. There may also be included one or more solvent, diluents, dispersants, wetting agents, adhesives and other pesticides. Other microbicidal compounds such as 3,4-dichlorobenzyl alcohol, diisobutyl phenoxyethoxyethyl dimethylbenzyl ammonium chloride, cetyl pyridinium chloride, cetyl trimethyl ammonium bromide, halogenated dihydroxydiphenyl-methanes, tetramethyl thiuram disulphide, 2,2\sv-thio-bis- (4,6-dichlorophenol), 2-nitro-2-furfuryliodide, salicyl anilides, dichlorosalicyl anilides, dibromosalicyl anilides, tribromosalicyl anilides, dichlorocyanuric acid, tetrachlorosalicyl anilides, aliphatic thiuram sulphides, hexachlorophen (2,2\sv-dihydroxy-3,5,6-3\sv,5\sv,6\sv-hexachloro diphenylmethane. The compositions may be in the form of semi-solid or liquid soaps, pastes, powders, emulsions, suspensions, solutions in organic solvents, sprays, granulates, tablets, pencils, in capsules from gelatin or other materials.