Patent GB-1120676-A (GB)
Title: Fluorene-imine derivatives and compositions containing them
Inventor: SCHMIDT KARL GUNTHER
IPC: C07C313/20
Filed: 1967-02-23
Abstract: Plants are treated with an N-trihalomethyl-thiofluorene-9-imine of the formula <FORM:1120676/C1/1> wherein R1 and R2 are H, halo, C1- 4 alkyl, NO2 or OH and X1, X2 and X3 are F, Cl or Br. Carriers are bolus, kaolin, bentonite, slate flour, talcum, chalk, dolomite, diatomaceous earth, xylene, petroleum ether, petrol, solvent naphtha, acetone, cyclohexane, dimethylformamide and dimethylsulphoxide. Additional regulants are indole-3-alkane-carboxylic acid, b -indolyl-butyric acid, gibberellin, gibberellinic acid, 6-(L-furfuryl)-aminopurine, b -chloroethyl-tri-methylammonium chloride, (4-hydroxy-5-isopropyl - 2 - methylphenyl) - trimethylammonium chloride, (5-isopropyl-2-methyl-4-(piperidinocarbonyloxy) - phenyl) - trimethyl-ammonium chloride, 1,11 - ethylene - 2,2I -dipyridinium dibromide, 1, 11 - dimethyl -4,41 - dipyridiniumdimethyl sulphate, phenyl-boric acid, 2 - chloro - 9 - hydroxy-fluorene - 9 - carboxylic acid, and 9 - hydroxyfluorene - 9 - carboxylic acid.  A composition may also contain urea.ALSO:Novel fluorene-imine derivatives with general formula <FORM:1120676/C2/1> where R1 and R2, which may be the same or different, are H, halogen, alkyl containing up to 4 carbon atoms, NO2 or OH, and X1, X2 and X3, which may be the same or different, are fluorine, chlorine or bromine; may be prepared by condensing a compound of the formula <FORM:1120676/C2/2> where R1 and R2 have the meanings specified above, R is -NH or <FORM:1120676/C2/3> and R3 is an acyl group; with a compound of the formula R4SCX1X2X3 where R4 is chlorine or bromine; in the presence of a basic condensation agent and an inert organic solvent.  X1, X2 or X3 may be exchanged for a different X1, X2 or X3 substituent by treatment with the appropriate hydrogen halide. These compounds are used as herbicides.ALSO:Herbicidal compositions comprise fluoreneimine derivatives of general formula <FORM:1120676/A5-A6/1> where R1 and R2, which may be the same or different, are H, halogen, alkyl containing up to 4 carbon atoms, NO2 or OH, and X1, X2 and X3, which may be the same or different, are fluorine, chlorine or bromine.  The action of these compounds is concentrated on the shoot tips (top buds) of plants; they act substantially selectively on tissue that is actively dividing and growing.  These compounds may be used in combination with other herbicides, e.g. substituted phenoxyalkane-carboxylic acids and their derivatives; substituted benzoic acids and other aryl carboxylic acids and their derivatives; substituted benzonitriles; arylphethalamide acids and derivatives; substituted phenylurea derivatives; N-phenylcarbamic acids and derivatives; triazole and its derivatives; triazines; pyridazones; uracils; picolinic acid and its derivatives; pyridinoles; phthalates; halogenated fatty acids and their derivatives; maleic hydrazide and its derivatives; indole-3-alkane-carboxylic acids and their derivatives; gibberellin; phytokinines; plant active quaternary nitrogen compounds; arylboric acids and derivatives of fluorene-9-carboxylic acid.