New heterocyclic carbamic acid esters, their preparation and use

摘要

Heterocyclic carbamic acid esters of the general formula wherein R represents hydrogen or methyl, X represents hydrogen or an alkyl radical with 1-4 carbon atoms, Y represents a halogen atom, the cyano, thiocyanato or nitro group, an alkyl or alkoxy radical having 1-4 carbon atoms, an alkanoyl radical having 2-12 carbon atoms, the benzoyl radical or a halogenated benzoyl radical, Z represents hydrogen, a halogen atom, an alkyl radical with 1-4 carbon atoms or an alkenyl radical with 3 or 4 carbon atoms, and p represents 0, 1 or 2, and their salts with organic and inorganic acids, may be made by a process which comprises reacting a compound of the general formula at a temperature of from 10 DEG to 100 DEG C. with an N-methyl carbamic acid chloride or bromide, with methyl isocyanate, with a mixture of N-methyl carbamic acid chloride and methyl isocyanate, with phosgene and methylamine or with chloroformic acid ethyl ester followed by treatment of the reaction product with methylamine. Examples describe the production of a considerable number of the heterocyclic esters, of which O - [2 - methyl - quinolyl - (8)] - N - methyl carbamic acid ester is typical.ALSO:A fungicidal seed dressing comprises a suitable carrier and/or dispersing agent and at least one heterocyclic carbamic acid ester or salt thereof of the general formula: wherein R represents hydrogen or methyl, X represents hydrogen or an alkyl radical with 1-4 carbon atoms, Y represents a halogen atom, a cyano, thiocyanato or nitro group, an alkyl or alkoxy radical having 1-4 carbon atoms, an alkanoyl radical having 2-12 carbon atoms, the benzoyl radical or a halogenated benzoyl radical, Z represents hydrogen, a halogen atom, an alkyl radical with 1-4 carbon atoms or an alkenyl radical with 3 or 4 carbon atoms, and P represents zero, 1 or 2. Examples describe seed dressings comprising kieselguhr, liquid paraffin, talcum and either O [5-benzoyl-quinolyl-(8)]- or O [5-(21, 51-di-bromobenzoyl)-quinolyl-(8)]-N-methylcarbamic acid ester. The carrier may comprise silicic acid, an organic solvent and/or water.ALSO:A fungicidal composition comprises a suitable carrier and/or dispersing agent and at least one heterocyclic carbamic acid ester of the general formula: wherein R represents hydrogen or methyl, X represents hydrogen or an alkyl radical with 1-4 carbon atoms, Y represents a halogen atom, the cyano thiocyanato or nitro group, an alkyl or alkoxy radical having 1-4 carbon atoms, an alkanoyl radical having 2-12 carbon atoms, the benzoyl radical or a halogenated benzoyl radical, Z represents hydrogen, a halogen atom, an alkyl radical with 1-4 carbon atoms or an alkenyl radical with 3 or 4 carbon atoms, and p represents 0, 1 or 2, or one or more salts thereof. Examples describe fungicidal compositions wherein the active ingredients are 0-[5-methyl-quinolyl-(8)]- and 0-[5-acetyl-quinolyl-(8)]-N-methyl-carbamic acid esters.