Bisthiocarbamic acid esters and herbicidal use thereof
AssigneeBASF SE
InventorsUlrich Schirmer, Bruno Wuerzer, Wolfgang Rohr
Life of this patent
Estimating the term…
Abstract
New diurethanes having a herbicidal action, the urethane radicals being attached to a phenyl radical in meta position and at least one of the urethane radicals containing sulfur; herbicides containing these compounds as active ingredients; processes for the preparation of these compounds; and processes for controlling the growth of unwanted plants with these compounds.
Claims9
A diurethane of the formula ##STR195## where Z denotes the radical ##STR196## and Y denotes the radical ##STR197## Z always being different from Y and R.sup.1 and R.sup.2 being identical or different and each denoting hydrogen, alkyl selected from the group consisting of methyl, ethyl and isopropyl, alkoxyalkyl selected from the group consisting of methoxymethyl and 2-methoxyethyl, methoxycarbonylmethyl, and chloromethyl, R.sup.3 and R.sup.4 being identical or different and each denoting methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, 2-ethylhexyl or n-decyl, 2-chloroethyl, 2-methoxyethyl, methoxycarbonyl methyl or lower alkyl substituted by phenyl or substituted aryl, the aryl substituent selected from the group consisting of 4-chlorophenyl and 2,4-dichlorophenyl, unsubstituted or halogen-substituted alkenyl selected from the group consisting of allyl, 2-chloropropen-(1)-yl-(3), butene-(1)-yl-(3), 2,3-dichloroallyl and 3,3-dichloro-2-methylallyl, unsubstituted or halogen- or alkoxy-substituted lower alkynyl, unsubstituted or alkyl-substituted cycloalkyl selected from the group consisting of cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,6-dimethylcyclohexyl, cycloheptyl, 4-tert-butylcyclohexyl, cyclooctyl, cyclododecyl and 3,5-dimethylcyclohexyl, 3,3,5-trimethylcyclohexyl, norbornyl, adamantyl, tricyclo-(4,3,1.sup.2,5,0.sup.1,6)-decyl, phenyl substituted with a fused ring system selected from the group consisting of naphthyl and indyl, phenyl or mono-or polysubstituted phenyl with the substituents lower alkyl, lower haloalkyl, lower alkoxyalkyl, lower alkoxycarbonylalkyl, cycloalkyl having 5 or 6 ring members, halogen, alkoxy, lower haloalkoxy, lower alkoxycarbonylalkoxy, nitro, amino, phenyl, phenoxy, thiocyanato, cyano ##STR198## R.sup.5 and R.sup.6 being identical or different and each denoting hydrogen, or phenyl and A, B, D and E being identical or different and each denoting oxygen or sulfur (with the proviso that one of these always denotes sulfur), X denotes hydrogen, lower alkyl, lower haloalkyl, lower alkoxy, halogen, nitro or amino, and n denotes one of the integers 1, 2, 3 and 4.
A process for combatting the growth of unwanted plants by treatment with a diurethane of the formula ##STR199## where Z denotes the radical ##STR200## and Y denotes the radical ##STR201## Z always being different from Y and R.sup.1 and R.sup.2 being identical or different and each denoting hydrogen, alkyl selected from the group consisting of methyl, ethyl and isopropyl, alkoxyalkyl selected from the group consisting of methoxymethyl and 2-methoxyethyl, methoxycarbonylmethyl, and chloromethyl, R.sup.3 and R.sup.4 being identical or different and each denoting methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, 2-ethylhexyl or n-decyl, 2-chloroethyl, 2-methoxyethyl, methoxycarbonylmethyl or alkyl substituted by phenyl or substituted aryl, the aryl substituent selected from the group consisting of 4-chlorophenyl and 2,4-dichlorophenyl, unsubstituted or halogen-substituted alkenyl selected from the group consisting of allyl, 2-chloropropen-(1)-yl-(3), butene-(1)-yl-(3), 2,3-dichloroallyl and 3,3-dichloro-2-methylallyl, unsubstituted or halogen- or alkoxy-substituted lower alkynyl, unsubstituted or alkyl-substituted cycloalkyl selected from the group consisting of cyclopentyl, 1-methylcyclopentyl, cyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,6-dimethylcyclohexyl, cycloheptyl, 4-tert-butylcyclohexyl, cyclooctyl, cyclododecyl and 3,5-dimethylcyclohexyl, 3,3,5-trimethylcyclohexyl, norbornyl, adamantyl, tricyclo-(4,3,1.sup.2,5,0.sup.1,6)-decyl, phenyl substituted with a fused ring system selected from the group consisting of naphthyl and indyl, phenyl or mono- or polysubstituted phenyl with the substituents lower alkyl, lower haloalkyl, lower alkoxyalkyl, lower alkoxycarbonylalkyl, cycloalkyl having 5 or 6 ring members, halogen, lower alkoxy, lower haloalkoxy, lower alkoxycarbonylalkoxy, nitro, amino, aryl, lower aryloxy, thiocyanato, cyano, ##STR202## R.sup.5 and R.sup.6 being identical or different and each denotinhg hydrogen, or phenyl and A, B, D and E being identical or different and each denoting oxygen or sulfur (with the proviso that one of these always denotes sulfur), X denotes hydrogen, lower alkyl, lower haloalkyl, lower alkoxy, halogen, nitro or amino, and n denotes one of the integers 1, 2, 3 and 4.
A diurethane selected from the group consisting of the compounds of the formulae ##STR203##
Dependencies are inferred from the claim text.