GB1216782A - Hydrazodicarboxylic amides and herbicides containing same - Google Patents

Abstract

1,216,782. Hydrazodicarboxylic amides. BADISCHE ANILIN- & SODA-FABRIK A.G. 20 May, 1968 [27 May, 1967], No. 23873/68. Heading C2C. [Also in Division A5] Novel compounds of the general formula wherein R 1 = phenyl which may bear one or more halogen atoms or C 1-4 alkyl, alkoxy, haloalkyl or nitro-substituents, or a cycloaliphatic radical which may bear one or more halogen atoms or C 1-4 alkyl groups; R<SP>2</SP>, R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> each = H, or a saturated or unsaturated aliphatic radical which may bear one or more halogen atoms, R<SP>6</SP> = phenyl which may bear one or more halogen atoms or C 1-4 alkyl, alkoxy or haloalkyl groups as substituents, or a cycloaliphatic radical of 3-8 C atoms which may bear halogen or C 1-4 alkyl groups, or a saturated or unsaturated radical which may bear a halogen or an acetoxy radical, are prepared by reacting a compound of general formula HN(R<SP>3</SP>)N(R<SP>4</SP>)H with R<SP>1</SP>N = C = O or R<SP>1</SP>N(R<SP>2</SP>)COX and one of the compounds R<SP>6</SP>N = C = O or R<SP>5</SP>N(R<SP>6</SP>)COX wherein X = halogen, if desired in the presence of an agent binding hydrogen halide. The preparations of the following compounds are exemplified: 1 - (m - chlorophenyl) - 3,6 - dimethylhydrazodicarboxylic amide, 1 - (2,5 - dichlorophenyl)- 3,6 - dimethylhydrazodicarboxylic amide, 1 - (2,5 - dichlorophenyl) - 4,6 - dimethylhydrazodicarboxylic amide, 1 - (m - chlorophenyl) - 4,6 - dimethylhydrazodicarboxylic amide and 1 - (phenyl) - 4,6,6 - trimethylhydrazodicarboxylic amide. 2 - Methyl - 4 - (m - chlorophenyl) - semicarbazide is prepared by reacting m-chlorophenyl isocyanate with methylhydrazine. 2- Methyl - 4 - (2,5 - dichlorophenyl) - semicarbazide; 2,4 - dimethyl - semicarbazide; 2- methyl - 4 - isopropyl - semicarbazide; 2 - methyl- 4 - p - ethoxyphenyl - semicarbazide and 2,4,4- trimethyl - semicarbazide are similarly obtained.