GB769222A - Esters of dithiocarbamic acids - Google Patents

Abstract

The invention comprises compositions of esters of dithiocarbamic acid, the amino group being unsubstituted or substituted by one or two alkyl, cycloalkyl, alkenyl, hydroxyalkyl or cyanoalkyl groups of not more than 8 carbon atoms, or bisdithiocarbamic esters with substituents forming a morpholinyl, piperidyl, or pyrrolidyl ring, or (in bis-compounds) a piperazine ring which may be alkylated on the 2- and 5-carbon atoms, the ester group in all cases being a haloalkenyl or haloalkadienyl group; and the dithiocarbamic esters of formula <FORM:0769222/IV(b)/1> in which R1 is hydrogen or one of the groups specified above, R2 is alkyl of 3 to 8 C and R3 is haloalkenyl or haloalkadienyl. The method of preparing the esters is by the reaction between a dithiocarbamic salt corresponding to the above formul and a dihaloalkene or dihaloalkadiene, only one halogen being removed. In examples the 3-chloro-2-butenyl-, 2-chloroallyl-, and 3-chloroallyl - N:N - dimethyldithiocarbamate, 3 - chloro - 2 - butenyldithiocarbamate; 2-chloroallyl-, 3 - chloro - 2 - butenyl -, and 3-chloroallyl - N:N - diethyldithiocarbamate, 3 - chloro - 2 - butenyl - 4 - morpholinecarbodithioate, and similar 2-chloroallyl- and 3-chloroallyl-derivatives, several chloroalkenyl-N:N-diallyl dithiocarbamates, bis-(21-chloroallyl)-2:5 - dimethyl - 1:4 - piperazine - carbodithioate and a table of similar compounds, are prepared by the action of the alkenyl dichlorides on the corresponding sodium or ammonium dithiocarbamic derivatives. Compounds in which the carbamic N is substituted by OH-alkyl and CN-alkyl are included. The products may be employed for weed-killers as sprays, emulsions, and dry compositions, and applied solid to earth and water (see Group VI).ALSO:Herbicidal compositions contain dithiocarbamic esters of the formul <FORM:0769222/VI/1> and <FORM:0769222/VI/2> in which R1 and R2 are hydrogen, alkyl cycloalkyl, alkenyl, hydroxy alkyl or cyanoalkyl, or R1, R2 and the N form a morpholinyl, piperidyl or pyrollidyl group, R3 is haloalkenyl or haloalkadienyl, R4 is hydrogen or alkyl, (see Group IV(b)), and dispersing agents or carriers. Carriers referred to include talc, clay, pyrophyllite and silica, and as solvents for dispersions acetone, chloroform, alcohol, benzene and heptane and other organic liquids. A number of dispersing agents are mentioned.