Patent GB-944454-A (GB)
Title: New dithiocarbamic acid derivatives and processes for their production
IPC: C07C333/16
Filed: 1962-01-15
Abstract: As nematoidal and fungicidal agents, which may be applied to the soil in admixture with fertilizers, use is made of dithiocarbamic esters of the formula <FORM:0944454/C1/1> where R is a cyclopentene-2-yl or a cyclopentyl radical, which may be substituted by halogen atoms, and (or) hydroxy groups, and R1 and R2 are hydrogen atoms or alkyl groups of 1-4 carbon atoms, R1 and R2 being the same or different (see Division C2).  The compounds may be applied in admixture with, e.g. calcium phosphate, ammonium sulphate, nitrates or potassium salts.ALSO:The invention relates to dithiocarbamic esters of the formula: <FORM:0944454/C2/1> where R is a cyclopentene-2-yl or a cyclopentyl radicle, which may be substituted by halogen atoms and (or) hydroxy groups, and R1 and R2 are hydrogen atoms or alkyl groups of 1-4 carbon atoms, R1 and R2 being the same or different.  The compounds may be prepared (a) by reacting a cyclopentene-2-yl or cyclopentyl halide with a salt of a dithiocarbamic acid of the formula: <FORM:0944454/C2/2> where R1 and R2 are as above; suitable cyclopentenyl or cyclopentyl derivatives for use in this reaction are cyclopentene-2-yl chloride, cyclopentyl chloride, 1, 2-dibromocyclopentene(2), or 1,2- or 1,3-dichlorocyclopentene-2; suitable dithiocarbamic salts are the sodium, potassium or ammonium salts; (b) by reacting a mercaptocyclopentene-(2) or mercaptocyclopentane with thiophosgene in the presence of an agent which binds hydrogen chloride, and treating the dithiocarbamic acid-cyclopentenyl ester chloride or the dithiocarbamic acid-cyclopentyl ester chloride so obtained with ammonia or a mono- or di-alkylamine; (c) by reacting mercaptocyclopentene-(2) or mercaptocyclopentane with an alkyl isothiocyanate; (d) by reacting mercaptocyclopentene-(2) or mercaptocyclopentane with an N-dialkyl-thiocarbamyl halide or (e) by reacting a cyclopentene or cyclopentadiene with a salt of a dithiocarbamic acid of the formula above in the presence of a mineral acid, the liberated dithiocarbamic acid then being added on to the double bond of the cyclopentene or to a double bond of the cyclopentadiene.  In the examples, (1) aqueous carbon disulphide is treated with methylamine and the mixture is stirred with sodium hydroxide to yield sodium monomethyl-dithiocarbamate; the latter is then treated with cyclopentienyl chloride to yield N-methylcyclopentene-(2)-yl dithiocarbamate; N-dimethyl-and N-diethyl-cyclopentene-(2)-yl dithiocarbamate and N-dimethyl-2-(or 3-)-chlorocyclopentene-(2)-yl dithiocarbamate are similarly obtainable; (2) mercaptocyclopentene-(2) is treated in benzene solution with methyl isothiocyanate to yield N-methylcyclopentene-(2)-yl dithiocarbamate. The products are useful as nematoidal and fungicidal agents and for these purposes they may be applied to the soil in solid form, in admixture with carriers, or they may be used as emulsions, solutions or suspensions.ALSO:As nematoidal and fungicidal agents, use is made of dithiocarbamic esters of the formula <FORM:0944454/A5-A6/1> where R is a cyclopentene-2-yl or a cyclopentyl radical, which may be substituted by halogen atoms and (or) hydroxy groups, and R1 and R2 are hydrogen atoms or alkyl groups of 1-4 carbon atoms, R1 and R2 being the same or different (see Division C2).  The products may be applied to the soil in solid form, in admixture with carriers, or they may be used as emulsions, solutions or suspensions.  Various methods of procedure are indicated, and examples and experimental results are given. The compounds may also be applied in admixture with fertilizers, e.g. calcium phosphate, ammonium sulphate, nitrates or potassium salts.