Patent GB-1122043-A (GB)
Title: Anilinoalkylcarboxamides and herbicidal compositions containing them
Inventor: YATES JOHN
IPC: C07C327/44
Filed: 1966-06-08
Abstract: The invention relates to anilino alkyl-carboxamides of the general formula <FORM:1122043/C2/1> wherein A represents a substituted or unsubstituted alkylene group of 1 to 6 carbon atoms; R1 and R2, which may be the same or different, each represents a hydrogen atom, a substituted or unsubstituted alkyl, aryl or alkenyl group, or a group NR3R4, wherein R3 and R4 each individually represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, provided that both of R1 and R2 are not hydrogen atoms or NR3R4 groups, or R1 and R2 together wit the nitrogen atom to which they are attached form a heterocyclic ring system optionally containing a further hetero atom; X, Y and Z, which may be the same or different, each represents a hydrogen or halogen atom, a cyano or nitro group, a substituted or unsubstituted alkyl or aryl group, an alkylsulphonyl group, or an amino or carbamoyl group or mono- or di-N-alkyl derivatives thereof, provided that not all of X, Y and Z represent hydrogen atoms.  Many compounds are claimed per se. The compounds in which at least one of the group X, Y and Z is a strongly electron-withdrawing group may be prepared by reacting a compound of the general formula <FORM:1122043/C2/2> with an amino acid NH2-A-COOH preferably in the presence of a base such as pyridine, sodium or potassium carbonate, bicaronate or hydroxide to give an acid having the general formula <FORM:1122043/C2/3> converting this acid into a corresponding acid chloride, e.g. by reaction with thionyl chloride in the presence of an inert solvent and reacting the acid chloride with an amine HNR1R2, wherein X, Y, Z, A, R1 and R2 are as above, with the proviso that at least one of the groups X, Y and Z is a strongly electron-withdrawing group and hal represents a fluorine, chlorine or bromine atom.  The compounds in which none of X, Y or Z represents a strongly electron-withdrawing group are prepared by reacting a compound of a general formula <FORM:1122043/C2/4> with a compound hal-A-COOR5 to give an ester having the formula <FORM:1122043/C2/5> and reacting this ester with an amine HNR1R2, wherein X, Y, Z, A, R1 and R2 have the meanings set forth in claim 1, with the proviso that none of the groups X, Y, Z shall represent a strongly electron-withdrawing group, hal represents a fluorine, chlorine or bromine atom and R5 represents an alkyl group containing 1-4 carbon atoms.  In an example, 1-chloro-2,6-dinitrobenzene is reacted with alpha-alanine to produce 2 - (2,6 - dinitroanilino) - propionic acid which is reacted with thionyl chloride to produce the acid chloride which is reacted with methylamine to yield N-methyl-2-(2,6-dinitroanilino) propionamide Many examples are given.ALSO:Herbicidal compositions comprise as active ingredient together with a carrier or surface active agent or both a carrier and surface active agent compounds of the general formula:  <FORM:1122043/A5-A6/1> wherein A represents a substituted or unsubstituted alkylene group of 1 to 6 carbon atoms; R1 and R2, which may be the same or different, each represents a hydrogen atom, a substituted or unsubstituted alkyl, aryl or alkenyl group, or a group NR3R4 wherein R3 and R4 each individually represents a hydrogen atom or an alkyl group of 1 to 4 carbon atoms, provided that both of R1 and R2 are not hydrogen atoms or NR3R4 groups, or R1 and R2 together with the nitrogen atom to which they are attached form a heterocyclic ring system optionally containing a further hetero atom; X, Y and Z, which may be the same or different, each represents a hydrogen or halogen atom, a cyano or nitro group, a substituted or unsubstituted alkyl or aryl group, an alkylsulphonyl group, or an amino or carbamoyl group or mono- or di-N-alkyl derivatives thereof, provided that not all of X, Y and Z represent hydrogen atoms.  The compounds may be formulated as wettable powders, dusts, granules, solutions, emulsifiable concentrates, emulsions and pastes, Many Examples of active ingredients, carriers and surface active agents are specified.