Patent GB-923128-A (GB)
Title: Herbicidal compositions and chemical compounds for use therein
Inventor: HAMM PHILIP CURTIS
IPC: C07C25/02
Filed: 1959-08-18
Abstract: Halogenated benzyl halides of formula:-  <FORM:0923128/IV(a)/1> in which each X and Y is a halogen atom, one of the two halogen atoms represented by X being present in the meta position with respect to the halomethyl group -CH2Y and the other halogen atom being in a non-vicinal position with respect to the halogen atom present in the meta position, are claimed as new compounds. They may be used as herbicides (see Group VI).  These compounds are prepared by mono-halogenation in the side chain of the corresponding nuclear halogenated toluenes at 150-200 DEG C., preferably in the presence of ultra violet light.  2.5-, and 3.5-dichlorobenzyl chlorides are specified.  Specification 781,702 is referred to.ALSO:A herbicidal composition comprises (1) from one to five parts by weight of one or more halogenated toluenes having the general formula <FORM:0923128/VI/1> in which X is a halogen atom, p is two, three, four or five, Y is a halogen atom, and n is zero, one, two or three and (ii) from 1 to 5 parts by weight of one or more N-substituted haloacetamides having the general formula <FORM:0923128/VI/2> in which Z is a halogen atom and (a) R and R1 are hydrogen atoms, aliphatic hydrocarbon groups having up to four carbon atoms or alkoxyalkyl and alkoxyalkoxyalkyl groups having up to eight carbon atoms, not more than one being a hydrogen atom; or (b) R is as defined under (a) and R1 is a cyclohexyl, alkyl cyclohexyl, benzyl or furfuryl group; or (c) R is any group defined under (a) except a hydrogen atom and R1 is a monocyclic aryl hydrocarbon group having up to ten carbon atoms. Of particular interest are the N-substituted chloroacetamides of formula <FORM:0923128/VI/3> in which R2 is an alkyl group having up to four carbon atoms, R3 is an alkyl group having up to four carbon atoms, and R4 is an alkylene group having from two to four carbon atoms and m is zero, one or two the total number of carbon atoms in R3 and R4 not exceeding 8.  The compositions may be formulated as dusts containing finely divided solid diluents or extenders, suitable solid diluents being china clays, bentonites, attapulgites, talc, pyrophyllite, quartz diatomaceous earth, fuller's earth, chalk, rock phosphate, sulphur, acid washed bentonite, precipitated calcium phosphate or carbonate and colloidal silica, the diluent constituting 55 to 95% of the formulation, or as liquids in solvents such as alcohols, ketones or hydrocarbons, e.g. isopropanol, benzene, acetone, methyl ethyl ketone and chlorinated hydrocarbons, with or without surface active agents e.g. a water-soluble salt of a long chain carboxylic acid, an amine salt of a long chain carboxylic acid, a sulphonated animal, vegetable or mineral oil, a quaternary ammonium salt containing a high molecular weight organic substituent in the quaternary ammonium group, a rosin soap such as a salt of abietic acid, a sulphonium salt containing a high molecular weight organic substituent in the sulphonium group, an algin soap or an ethylene oxide condensation product with a fatty acid, an alkyl phenol or a mercaptan.  The surface active agent may constitute 0.05 to 10% of the formulation and may be mixed with the active ingredients alone.  In addition the herbicidal compositions may contain insecticides, fungicides, nematocides and other herbicides, e.g. 2, 4 dichlorophenoxy acetic acid or an ester amine salt or alkali metal salt thereof.  Typical active ingredients are N,N-dimethyl; N-propyl N-phenyl; N-furfuryl; N-(3-ethoxy propyl) - chloroacetamide; and 2,3,6 trichlorobenzyl chloride, 2,3,4 trichlorotoluene and 2,3,4,6 tetrachlorobenzylchloride.  For preparation of the benzyl halides (see Group IV (b)). Specification 781,702 is referred to.