Patent GB-1078347-A (GB)
Title: Fluorene-9-carboxylic acid derivatives, process for their preparation and compositions containing them
IPC: C07C243/36
Filed: 1965-11-10
Abstract: The invention relates to fluorene-9-carboxylic acid derivatives of the general formula <FORM:1078347/C2/1> where R1 and R2, which may be the same or different, are H, Cl, Br or I; R3 is H, OH or Cl; and Z is OR4, -NH-NH2 or <FORM:1078347/C2/2> where R4 is a straight or branched mono- or poly-unsaturated alkenyl or alkinyl radical with up to 6 carbon atoms which may, if desired, be mono- or poly-substituted by OH and/or a halogen, or is an alkyl radical with 1-12 carbon atoms, the alkyl chain of which is interrupted by from 1 to 4 non-adjacent O- and/or S-atoms and/or is substituted by from 1 to 3 hydroxy groups or halogen atoms, by phenyl or naphthyl or by a phenyl or naphthyl radical substituted by from 1 to 3 hydroxy groups or halogen atoms or a methylenedioxy group, or an aromatic or cycloaliphatic radical with 5-10 carbon atoms which may, if desired, be substituted by from 1 to 3 halogen atoms or hydroxy groups or a methylene dioxy group, or a sustituted ammonium cation derived from an aliphatic or cycloaliphatic amine which contains 1-22 carbon atoms and the hydrocarbon chain(s) of which may, if desired, be interrupted by O- or NH and/or be substituted by OH or NH2 groups; and R5 is H, OH or Cl, but wherein R1, R2 and R5 are not simultaneously H. Examples of many compounds described and claimed are: 9 - Fluorenol - 9 carboxylic acid allyl - ester; 9 - fluorenol - 9 - carboxylic acid 31 - chloro - butenyl - (21) - ester; 9 - fluorenol - 9 carboxylic acid 21,31,31-trichloroallyl-ester; 9-fluorenol-9-carboxylic acid soya oil amine salt; 2 - chloro - 9 - fluorenol - 9 - carboxylic acid 31-chloro-butenyl-(21)-ester.  The compounds may be prepared by reacting a compound of the general formula <FORM:1078347/C2/3> in which R1, R2, R3 are as above and X is OH, lower alkoxy, Cl, ONa, OK or OAg, with a compound of the formula R4Y, where R4 is as above, and Y is OH or halogen, preferably chlorine or bromine, or with hydrazine or a salt thereof, or with aniline or an R5-substituted aniline where R5 is as above, or with a primary, secondary or tertiary amine containing the radical R4. Chlorine, bromine or iodine may be introduced into the 2 and/or 7 positions by treating with elemental chlorine, bromine or iodine.ALSO:A plant morphology regulating composition comprises one or more fluorene-9-carboxylic acid derivatives of the general formula (I) <FORM:1078347/A5-A6/1> in which R1 and R2, which may be the same or different, are H, Cl Br or I; R3 is H, OH or Cl; and Z is OR4, -NH-NH2 or (II) <FORM:1078347/A5-A6/2> where R4 is straight or branched mono- or poly-unsaturated alkenyl or alkynyl radical with up to 6 carbon atoms which may, if desired, be mono- or poly-substituted by OH and/or a halogen, or is an alkyl radical with 1-12 carbon atoms, the alkyl chain of which is interrupted by from 1 to 4 non-adjacent 0-and/or S-atoms and/or is substituted by from 1 to 3 hydroxy groups or halogen atoms, by phenyl or naphthyl or by a phenyl or naphthyl radical substituted by from 1 to 3 hydroxy groups or halogen atoms or a methylenedioxy group, or an aromatic or cycloaliphatic radical with 5-10 carbon atoms which may, if desired, be substituted by from 1 to 3 halogen atoms or hydroxy groups or a methylene dioxy group, or a substituted ammonium cation derived from an aliphatic or cycloaliphatic amine which contains 1-22 carbon atoms and the hydrocarbon chain(s) of which may, if desired, be interrupted by O- or NH and/or be substituted by OH or NH2 groups; and R5 is H, OH or Cl, but wherein R1, R2 and R5 are not simultaneously H.  Many active ingredients are specified.  The composition may also contain one or more herbicidal and/or growth regulating substances many being specified.