Oxaboroles and salts thereof, and their use as biocides
AssigneeZeneca Limited
InventorsPeter William Austin, Christopher Juan Kneale, Patrick Jelf Crowley, John Martin Clough
Life of this patent
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Abstract
A method for the protection of a medium by susceptible to microbial attack by the treatment of the medium with an oxaborale or a salt of an oxaborale.
Claims23
A method for the protection of a medium susceptible to microbial attack by the treatment of the medium with an effective amount of an oxaborole of formula (1) ##STR16## or a salt thereof:
- wherein
- A and D together with the carbon atoms to which they are attached form a 5, 6, or 7-membered fused ring which may be substituted by C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, hydroxy, halogen, nitro, nitrile, amino, amino substituted by one or more C.sub.1-6 -alkyl groups, , carboxy, acyl, aryloxy, carbonamido, carbonamido substituted by C.sub.1-6 -alkyl, sulphonamido or trifluoromethyl or the fused ring may link two oxaborole rings;
- X is a group --CR.sup.1 R.sup.2 wherein R.sup.1 and R.sup.2 are each, independently, hydrogen, C.sub.1-6 -alkyl, nitrile, nitro, aryl, aralkyl or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an alicyclic ring;
- and
- R is hydrogen, C.sub.1-18 -alkyl, (C.sub.1-18 -alkyl substituted by C.sub.1-6 -alkoxy, C.sub.1-6 -alkylthio, hydroxy, amino, amino substituted by C.sub.1-18 -alkyl, , carboxy, aryl, aryloxy, carbonamido, ( carbonamido substituted by C.sub.1-6 -alkyl, aryl or aralkyl), aralkyl, aryl, heteroaryl, cycloalkyl, C.sub.1-18 -alkyleneamino, C.sub.1-18 -alkyleneamino substituted by phenyl, C.sub.1-6 -alkoxy or C.sub.1-6 -alkylthio, carbonyl alkyleneamino or a radical of formula (2) ##STR17## wherein A, D and X are as defined hereinbefore except for boronophthalide.
A process for making an oxaborole of formula 1 wherein A and D together with the carbon atoms to which they are attached form a fused phenyl ring which comprises reacting on o-substituted halogeno toluene with magnesium or alkyl-lithium in a inert solvent and reacting the Grignard reagent or aryl lithium so formed with a borate ester to obtain a toluene boronic acid which is then reacted with a brominating agent followed by hydrolysis to give a hydroxymethylbenzene boronic acid and cyclising the boronic acid under acid conditions to give a benzoxaborole.
A process for making an oxaborole of formula 1 wherein A and D together with the carbon atoms to which they are attached form a fused phenyl ring which comprises reacting an optionally substituted benzaldehyde with p-toluenesulphonylhydrazide in an inert solvent followed by reaction with boron tribromide and catalyst to give a 1,2-dihydro-1-hydroxy-2-(4-methylphenylsulphonyl)-2,3,1-benzodiazaborine which is then hydrolysed and cyclised to form a benzoxaborole.
A process for making an oxaborole of formula 1 wherein A and D together with the carbon atoms to which they are attached form a fused aromatic ring which comprises reacting an aromatic compound containing a --CH.sub.2 OH group with alkyl or aryl-lithium and an organo-borate in a dry inert liquid.
A process for making an oxaborole of formula 1 wherein A and D together with the carbon atoms to which they are attached form a fused aromatic ring which comprises reacting an aromatic compound containing a --CH.sub.2 OH group and an ortho chloro or fluoro group with alkyl or aryl lithium and an organo-borate in an inert organic liquid.
Dependencies are inferred from the claim text.