Patent GB-828871-A (GB)
Title: Herbicidal compositions
Inventor: HACKMANN JOHANNES THOMAS
IPC: A01N47/06
Filed: 1957-07-12
Abstract: The invention comprises carbamic acid esters of the formula R1R2NCO.O.CHClR, wherein R represents an aliphatic hydrocarbon group of 1 to 4 carbon atoms or a phenyl group which groups may carry at least one substituent halogen atom preferably chlorine, and wherein R1 and R2 each signify a hydrogen atom or an aliphatic hydrocarbon group of 1 to 4 carbon atoms which may be unsaturated, or a cycloaliphatic or aromatic hydrocarbon group which groups may carry at least one substituent halogen atom preferably chlorine, or R1 and R2 may be linked to complete with the nitrogen atom a heterocyclic ring. The above compounds are prepared by reacting phosgene or an equivalent amount of diphosgene or triphosgene with an equimolecular proportion of an aldehyde RCHO in the presence of a tertiary nitrogenous base to produce an initial addition product ClCO.O.CHClR then reacting this with ammonia or a primary or secondary amine, e.g. diethylamine, n-propylamine, di-n-propylamine, allylamine, diallylamine, propynylamine, aniline, methylaniline, 1 : 3 : 5-trichloroaniline, 4-chloroaniline, piperidine or morpholine, to produce the carbamic acid ester.  Exemplary of such compounds are 1 : 2 : 2 : 2-tetrachloroethyl-N-allyl carbamate and 1 : 2 : 2 : 2-tetrachloroethyl-N-diallyl carbamate.  Preferred among the aldehydes used to form the initial product is chloral, but others exemplified are acetaldehyde, 1 : 2-dibromopropionaldehyde, 1 : 1 - dichloropropionaldehyde, 1 : 1 : 2 - trichlorobutyraldehyde, 2 - chloro - acrolein, benzaldehyde, 2-chlorobenzaldehyde, 4-chlorobenzaldehyde and 2 : 4-dichlorobenzaldehyde.  The Specification also describes the preparation of compounds of the formula OC(OCHClR)2 from the reaction between the initial addition product above and a further molecular proportion of an aldehyde RCHO. Exemplary of such compounds are di-(1 : 2 : 2 : 2-tetrachloroethyl) carbonate, and di - [1 - chloro - 1 - (2 - chloro - phenyl) methyl] carbonate.  A further process which produces unsymmetrical carbonic acid esters of formula R1O.CO.O.CHClR is disclosed in which the initial addition product above is reacted with an aliphatic, preferably unsaturated, alcohol R1OH having 1 to 8 carbon atoms, e.g. allyl alcohol diallyl alcohol or proparzyl alcohol. Specification 815,510 is referred to.ALSO:Herbicidal compositions comprise a surface-active agent or a solid carrier or a hydrocarbon oil or a surface-active agent and a solid or liquid carrier and a compound having the general formula YCO.O.CHClR where R represents an aliphatic hydrocarbon group of 1 to 4 carbon atoms or a phenyl group which groups may carry at least one substituent halogen atom, and Y represents a group O.CHClR, R being as above specified, or a group OZ, where Z is a hydrocarbon group of 1 to 8 carbon atoms which may be unsaturated, or Y represents a group NR1R2 wherein R1 and R2 each signify a hydrogen atom or an aliphatic hydrocarbon group of 1 to 4 carbon atoms, which may be unsaturated, or a cycloaliphatic group or aromatic hydrocarbon group, which groups may carry at least one substituent halogen atom, or R1 and R2 may be linked to complete with the nitrogen atom a heterocyclic group.  Preferably the halogen is chlorine.  For the preparation of such compounds (see Group IV (b)). Compounds exemplified in the Specification are di-(1 : 2 : 2 : 2-tetrachloroethyl) carbonate, di - [1 - chloro - 1 - (2 - chlorophenyl)-methyl] carbonate, 1 : 2 : 2 : 2 - tetrachloroethyl N-allylcarbamate and 1 : 2 : 2 : 2-tetrachloroethyl N - diallylcarbamate.  The compositions may take the form of liquids or solids and as concentrates which may be subsequently diluted.  Such carriers or additives which may be present include surface-active agents of the non-ionic type, e.g. condensation products of ethylene oxide with oleyl alcohol, abietic acid and p-octylphenol; finely-powdered solids, e.g. talc, clay, kieselguhr, silica, carbon and fuller's earth; water conditioning agents, e.g. sodium phosphate, sodium polyphosphate or cellulose ethers, e.g. methyl cellulose, or sodium salt of cellulose glycollic acid.  Liquid carriers are preferably a hydrocarbon oil, e.g. kerosine gas oil or lubricating oil fraction, or aqueous acetone solutions.  Specification 815,510 is referred to.