4-SUBSTITUTED-ALKYL-1,3,4-THIADIAZOLON-(5)-YL-(2)-UREA COMPOUNDS

• Main Authors: SASSE K,DT, EUE L,DT
• Format: Patent
• Language: English
• Published: 08.10.1974
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

1344039 1,3,4 - Thiadiazolon - 5 - yl ureas BAYER AG 15 May 1972 [15 May 1971] 22722/72 Heading C2C Novel 1,3,4-thiadiazolon-5-yl ureas of the Formula (I) wherein R is a C 2-5 alkenyl group optionally substituted by phenyl, a C 2-5 alkynyl group or a C 1-5 alkyl radical which is substituted by at least one of the following: optionally substituted aryloxy, alkylmercapto, optionally substituted arylmercapto, alkylsulphinyl, arylsulphinyl, alkylsulphonyl, arylsulphonyl, dialkylamino, alkoxycarbonyl, carboxylic acyl, amino carbonyl, N-mono- or N,N-disubstituted aminocarbonyl, morpholinyl, nitro or cyano groups; R1 and R2 are hydrogen atoms or C 1-3 alkyl groups and R3 is alkyl, allyl or alkoxy with 1 to 4 carbon atoms; are obtained by reacting the corresponding 4-unsubstituted 1,3,4-thiadiazolon-5-yl ureas with compounds of the formula R-X, X being a halogen atom or a sulphuric acid or sulphonic acid ester radical, the urea derivative being in the form of a salt or the reaction being conducted in the presence of an acid-binding , agent. The 4-unsubstituted 1,3,4-thiadiazol-5-yl ureas, used as starting materials (i.e. compounds of Formula I above wherein R is a hydrogen atom) may be obtained by reacting phosgene with 1-alkanoyl-4-alkylthiosemicarbazides and reacting the resulting 1,3,3-thiodiazolon-5-yl carbonyl chlorides with amines of the formula R2NHR3. A herbicidal composition, comprises as active ingredient a compound of the Formula I above in admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.