Patent GB-1008851-A (GB)
Title: Substituted alpha-haloacetanilides and herbicidal compositions containing them
IPC: C07C233/00
Filed: 1962-08-24
Abstract: The invention comprises a -haloacetanilides having the generic formula <FORM:1008851/C2/1> selected from the following classes: (1) compounds wherein q is O; m is 1; R1 is a t-alkyl radical; R2 attached in the 6 position is an alkyl radical or an alkoxy radical; and X is chlorine, bromine or iodine; (2) compounds where q is O; R1 is a t-alkyl radical; m is 2; one R2 is primary alkyl or secondary alkyl attached in the 6 position, the other R2 is primary alkyl, secondary alkyl, a chlorine atom or a nitro group attached in the 5 position; and X is chlorine, bromine or iodine; (3) compounds where q is 1; R3 is primary or secondary alkylene, oxaalkylene, alkenylene, or alkynylene; R1 is t-alkyl, m is 1; R2 is alkyl attached in the 6 position; and X is chlorine, bromine or iodine; (4) compounds where q is 0 or 1; R3 is alkylene or alkenylene; m is 2 and the two R2's are taken together with the phenyl group to which they are attached to form a naphthyl group; R1 is a t-alkyl group; and X is chlorine, bromine or iodine; (5) compounds where q is O, R1 is t-alkyl, m is 1 and there is either a halogen atom in the 6 position or a primary or secondary alkyl group in the 5 position, and X is chlorine, bromine or iodine; (6) compounds where q is 1, R3 is alkenylene, m is 1 or 2, R1 is a hydrogen atom, a primary or secondary alkyl radical, or a halogen atom; if there is a substituent in the 6 position it is a primary or secondary alkyl radical; if there is a substituent in the 5 position it is a primary or secondary alkyl radical or a halogen atom; provided that when m is 2 then R1 is a hydrogen atom but not otherwise; and X is a chlorine atom; and (7) compounds where q is O, R1 is a C1-C4 primary or secondary alkyl, m is 1, R2 is a C2 to C4 primary or secondary alkyl attached in the 6 position, provided R1 and R2 have a total of at least 4 carbon atoms; and X is chlorine, bromine or iodine.  The compounds may be made by reacting an amine of the formula <FORM:1008851/C2/2> or <FORM:1008851/C2/3> as appropriate with an appropriate haloacetylation agent, preferably either a haloacetic anhydride or a haloacetyl halide. The reaction preferably takes place in a suitable liquid reaction medium such as benzene, diethyl ether, hexane, methylethyl ketone, chlorobenzene, toluene, chloroform and the xylenes.  An acid acceptor such as an amine, alkali or alkaline earth hydroxide, carbonate or bicarbonate may also be present.  Temperature of 0 DEG  to 15 DEG  C. are desirable. Specification 781,702 is referred to.ALSO:A herbicidal composition comprises a herbicide adjuvant and an alpha-haloacetanilide of the formula <FORM:1008851/A5-A6/1> the composition being a particulate solid, or a liquid containing a surface-active agent, and the alpha-haloacetanilide being selected from:  (1) compounds where q is 0, m is 1, R1 is a t-alkyl, R2 is an alkyl or alkoxy radical in the 6 position, and X is chlorine, bromine or iodine;  (2) compounds where q and m are both 0, R1 is a t-alkyl, X is chlorine, bromine or iodine;  (3) compounds where q is 0, R1 is t-alkyl, m is 2, there is a primary or secondary alkyl in the 6 position and a primary or secondary alkyl, chlorine atom or nitro group in the 5 position, and X is chlorine, bromine or iodine;  (4) compounds where q is 1, R3 is primary or secondary alkylene, oxaalkylene, alkenylene, or alkynylene; R1 is t-alkyl, m is 1, R2 is alkyl in the 6 position, and X is chlorine, bromine or iodine;  (5) compounds where q is 0 or 1, R3 is alkylene or alkenylene, m is 2, and the two R2's are taken together with the phenyl group to which they are attached to form a naphthyl group; R1 is a t-alkyl group; and X is chlorine, bromine or iodine;  (6) compounds where q is 0, R1 is t-alkyl, m is 1, and thereis either a halogen atom in the 6 position or a primary or secondary alkyl in the 5 position, and X is chlorine, bromine or iodine;  (7) compounds where q is 1, R3 is alkylene or alkenylene, m is 1 or 2, R1 is a hydrogen atom, a primary or secondary alkyl, or a halogen atom; any substituent in the 5 position, is a primary or secondary alkyl or a halogen atom, any substituent in the 6 position is a primary or secondary alkyl, provided that when m is 2 then R1 is a hydrogen atom but not otherwise, and X is a chlorine atom; and, (8) compounds where q is 0, R1 is a C1-C4 primary or secondary alkyl, m is 1, R2 is a C2-C4 primary or secondary alkyl in the 6 position, and X is chlorine, bromine or iodine.  The herbicidal adjuvants include solid or liquid extending agents such as solvents or diluents, wetting or emulsifying agents and adhesive agents or spreading agents.  Examples of liquid and solid extending agents are given, as well as anionic, cationic and non-ionic wetting agents.  As solid carriers there may also be employed solid fertilisers such as ammonium nitrate, urea and superphosphate as well as other materials in which plants grow, such as compost, manure, humus and sand.  The compositions may be applied as dusts or sprays.  Specification 781,702 is referred to.