Patent GB-1087561-A (GB)
Title: Fluorinated benzimidazoles and compositions containing them
Inventor: BURTON DENNIS ERNEST
IPC: C07D235/10
Filed: 1963-02-16
Abstract: Lubricating oil may contain a wetting agent such as oleic acid and a 2-trifluoromethyl- or 2-pentafluoroethyl-benzimidazole.ALSO:The invention comprises (i) the salts of compounds of the general formula <FORM:1087561/C2/1> wherein X is CF3 or C2F5, and R1, R2, R3 and R4 are the same or different and selected from hydrogen, alkyl, hydroxy, alkoxy, nitro, halogen, pseudo-halogen, substituted alkyl, carboxy, carboxy ester, carboxy amide, N-substituted carboxy amide, N-disubstituted carboxy amide, amino, mono- or di-substituted amino, thiol, alkylthiol and oxygenated derivatives thereof, sulphonic acid, ester and amide radicals; (ii) compounds of the above general formula where X, R1, R2, R3 and R4 are as defined above but excluding the cases where X is CF3 and where R1 is H, CF3, CH3, OCH3 or COOH, or where R2 is F, Cl, CH3, CF3, OCH3 or NO2, or where R1 and R2 are both CH3 or CF3, or where R1 and R4 are the same and are CH3 or OC2H5, or where R2 and R3 are both CH3, when the remaining groups R1 to R4 are H, or where R1, R2, R3 and R4 are all F, and excluding those cases where X is C2F5 and either where R1 to R4 are all H or F or where R1 and R4 are CH3 and R2 and R3 are H.  The salts may be prepared by reacting the parent benzimidazole with an alkaline compound of a metal, with an amine or with a strong acid, as appropriate, or by metathesis.  The benzimidazoles may be prepared by (i) reacting the appropriate orthophenylene diamine with trifluoroacetic or pentafluoropropionic acids or the chlorides or anhydrides thereof; (ii) nitrating an appropriate benzimidazole to form a nitro-substituted benzimidazole; or (iii) forming an amino-substituted benzimidazole by reduction of the corresponding nitro-substituted benzimidazole.ALSO:A process for the treatment of plants, the soil, land or aquatic areas comprises applying thereon or thereto (i) a composition which contains as an active ingredient a compound of the formula <FORM:1087561/A5-A6/1> or a salt thereof, wherein X is CF3 or C2 F5, and R1, R2, R3 and R4 are the same or different and selected from H, alkyl, OH, O, alkyl, NO2, halogen, pseudo-halogen, substituted alkyl, COOH, carboxy ester, carboxy amide, N-substituted carboxy amide, N-disubstituted carboxy amide, amino or mono- or disubstituted amino, thiol, alkylthiol and oxygenated derivatives thereof, sulphonic acid, ester and amide radicals, together with at least one material selected from wetting agents and solid inert diluents, (ii) a salt of a substituted benzimidazole as defined above, or (iii) in a substituted benzimidazole as defined above excluding the cases where X is CF3 and where R1 is H, CH3, CF3, OCH3 or COOH, or where R2 is F, Cl, CH3, CF3, OCH3 or NO2, or where R1 and R2 are both CH3 or CF3, or where R2 and R4 are the same and are CH3 or OC2H5, or where R2 and R3 are both CH3, when the remaining groups R1 to R4 are H, or where R1, R2, R3 and R4 are all F, and excluding those cases where X is C2F5 and either where R1 to R4 are all H or F or where R1 and R4 are CH3 and R2 and R3 are H.