Mono-iodopropargyl esters of dicarboxylic anhydrides and their use as antimicrobial agents
AssigneeLonza Ltd.
InventorChuen-Ing J. Tseng
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AssigneeLonza Ltd.
InventorChuen-Ing J. Tseng
Estimating the term…
The new compositions of matter of the present invention comprise compounds having one of the following formulas: ##STR1## wherein: R is hydrogen or methyl; n is 1 to 16; R.sub.1 and R.sub.2 are defined as R.sub.3 and R.sub.4 below or are joined to form a cycloalkyl, cycloalkenyl, aromatic or a heterocyclic ring containing an oxygen, nitrogen or sulfur atom or an alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl substituted derivative thereof; R.sub.3 and R.sub.4 are independently selected from (A) hydrogen, alkyl, cycloalkyo, alkenyl, cycloalkenyl, aryl, a heterocyclic ring containing an oxygen, nitrogen or sulfur atom, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl and (B) substituted derivatives of the alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl and the heterocyclic ring wherein the substitutions are alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl; W may be a single bond, oxygen, NR.sub.5, or (CR.sub.6 R.sub.7).sub.m, wherein R.sub.5 is hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl or a heterocyclic ring containing an oxygen, nitrogen or sulfur atom or a substituted derivative of alkyl, cycloalkyl, alkenyl, cycloalkenyl or aryl groups wherein the substitutions are alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkoxy, amino, carboxyl, halo, hydroxyl, keto or a thiocarboxyl where R.sub.6 and R.sub.7 are defined as R.sub.3 and R.sub.4 above and m is an integer from 1 to 12; and X is hydrogen or a salt-forming cation. Examples of such compositions are mono-iodopropargyl succinates, maleates, itaconates, diglycolates and phthalates. Other compounds include the mono-iodopropargyl esters of anhydrides such as dimethylglutaric anhydride and ethylenediamine tetraacetic dianhydride. They are used in microbiocidal formulations and effective microbiocides.
A compound having one of the following formulas:
Iodopropargyl succinate.
Iodopropargyl phthalate.
Iodopropargyl diglycolate.
Iodopropargyl maleate.
Iodopropargyl itaconate.
Chlorhexidine iodopropargyl diglycolate.
A process for preparing a mono-iodoalkenyl ester of a dicarboxylic acid anhydride which comprises reacting equimolar quantities of an iodoalkynyl alcohol having from 3 to 6 carbon atoms with a dicarboxylic acid anhydride in the presence of a catalytic amount of a tertiary amine in a non-alcoholic organic solvent.
Dependencies are inferred from the claim text.