GB1398312A - Aminonitrophenylsulphonamides and herbicidal compositions containing them - Google Patents

Abstract

1398312 Sulphonamides SHELL INTERNATIONALE RESEARCH MAATSCHAPPJI NV 5 June 1972 [7 June 1971(2) 25 Aug 1971] 26081/72 Heading C2C The invention comprises compounds of Formula III wherein R<SP>1</SP> and R<SP>2</SP> each independently represents an alkyl group of up to 4 carbon atoms, an alkenyl group of up to 4 carbon atoms or cycloalkyl of up to 6 carbon atoms; and A represents (a) the group wherein R<SP>3</SP> is hydrogen, alkyl of up to 4 carbon atoms, alkenyl of up to 4 carbon atoms, wherein R<SP>5</SP> is hydrogen, alkyl of up to 4 carbon atoms, alkenyl of up to 4 carbon atoms, cycloalkyl of up to 6 carbon atoms, -OR<SP>6</SP>, wherein R<SP>6</SP> is alkyl of up to 4 carbon atoms, or -NR<SP>7</SP>R<SP>8</SP>, wherein R<SP>7</SP> is hydrogen and R<SP>8</SP> is alkyl of up to 4 carbon atoms, Q is oxygen or sulphur with the proviso that when Q is oxygen, R<SP>4</SP> is hydrogen, a lower alkali metal ion, a quaternary ammonium group, wherein the cationic nitrogen is substituted with up to 4 alkyl groups each containing up to 3 carbon atoms, alkyl of up to 4 carbon atoms, cycloalkyl of up to 6 carbon atoms, or wherein R<SP>9</SP> is hydrogen, alkyl of up to 4 carbon atoms, alkenyl of up to 4 carbon atoms or -OR<SP>6</SP>, wherein R<SP>6</SP> is as described above and when Q is sulphur, R<SP>3</SP> is wherein R<SP>5</SP> is as described above and R<SP>4</SP> is alkyl of up to 2 carbon atoms, wherein all the hydrogens have been replaced by chlorine and/or fluorine; or (b) the group wherein R<SP>10</SP> and R<SP>11</SP> each independently represents an alkyl group of up to 4 carbon atoms; or (c) the group wherein R represents alkyl of up to 4 carbon atoms or alkyl of up to 2 carbon atoms in which all the hydrogen substituents on the alkyl moieties are replaced with chlorine and/or fluorine. The compounds I in which A represents the group -N(R<SP>3</SP>)OR<SP>4</SP> are prepared by reacting a compound of Formula II with a compound R<SP>4</SP>O-NHR<SP>3</SP> in which each of R<SP>3</SP> and R<SP>4</SP> is H or the appropriate alkyl, alkenyl or cycloalkyl group, and optionally treating the product with a carboxylic anhydride, alkyl isocyanate or alkyl chloroformate. The compounds I in which A represents the group -N(R<SP>3</SP>)SR<SP>4</SP> are prepared by reacting a compound of Formula IV with a compound ClSC n X (2 n +1) in which X is Cl or F and n=1 or 2. The compounds I in which A represents the group -N=C(R<SP>11</SP>)OR<SP>10</SP> are prepared by reacting a compound II with a compound HN=C(R<SP>11</SP>)OR<SP>10</SP>. The compounds I in which A represents the group are prepared by reacting a compound II with a compound H 2 N-C(R)=NH. N - (4 - (dipropylamino) - 3,5 - dinitrobenzenesulphonyl)acetamide is prepared by reacting 4 - (dipropylamino) - 3,5 - dinitrobenzenesulphonamide with acetic anhydride. Trifluoroacetamidine is prepared by reacting trifluoroacetonitrile with ammonia. Herbicidal compositions comprise a compound I together with an adjuvant therefor.