2,3-Dihalo-2,3-(disubstituted) propanoate antimicrobial compounds

An antimicrobial composition comprising a carrier and an antimicrobially effective amount of a compound of the formula:

• ##STR13## wherein Hal is bromine or chlorine;
• R is C.sub.1-4 alkyl, straight or branched chain;
• and
• one of R.sup.1 and R.sup.2 is hydrogen and the other is selected from the group consisting of C.sub.3-8 cycloalkyl;
• C.sub.3-8 cycloalkyl C.sub.1-3 alkyl;
• phenyl;
• phenyl C.sub.1-3 alkyl;
• mono- or disubstituted phenyl or phenyl C.sub.1-3 alkyl wherein the substituents are halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, nitro, cyano, or trifluoromethyl;
• a heterocyclic radical selected from the group consisting of thienyl, furanyl, pyrrolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, and pyridinyl, and N-oxides thereof;
• and a saturated heterocyclic radical selected from the group consisting of pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, isoxazolidinyl, oxazolidinyl, isothiazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperazinyl, and piperidinyl.

A method of inhibiting the growth of at least one of:

• bacteria, fungi, and algae, comprising contacting said bacteria, fungi, or algae, with a bactericidally, fungicidally, or algicidally effective amount of a compound of the formula:
• ##STR14## wherein Hal is bromine or chlorine;
• R is C.sub.1-4 alkyl, straight or branched chain;
• and
• one of R.sup.1 and R.sup.2 is hydrogen and the other is selected from the group consisting of C.sub.3-8 cycloalkyl;
• C.sub.3-8 cycloalkyl C.sub.1-3 alkyl;
• phenyl;
• phenyl C.sub.1-3 alkyl;
• mono- or disubstituted phenyl or phenyl C.sub.1-3 alkyl wherein the substituents are halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, nitro, cyano, or trifluoromethyl;
• a heterocyclic radical selected from the group consisting of thienyl, furanyl, pyrrolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, and pyridinyl, and N-oxides thereof;
• and a saturated heterocyclic radical selected from the group consisting of pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, isoxazolidinyl, oxazolidinyl, isothiazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperazinyl, and piperidinyl.

A method of inhibiting the growth of slime-forming bacteria, fungi, and algae usually encountered in pulp and paper mill systems, comprising incorporating into the mass of fiber and water in such a pulp and paper mill system so as to contact said bacteria, fungi, and algae, at least a bactericidally, fungicidally, and algicidally effective amount of a compound of the formula:

• ##STR15## wherein Hal is bromine or chlorine;
• R is C.sub.1-4 alkyl, straight or branched chain;
• and
• one of R.sup.1 and R.sup.2 is hydrogen and the other is selected from the group consisting of C.sub.3-8 cycloalkyl;
• C.sub.3-8 cycloalkyl C.sub.1-3 alkyl;
• phenyl;
• phenyl C.sub.1-3 alkyl;
• mono- or disubstituted phenyl or phenyl C.sub.1-3 alkyl wherein the substituents are halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxy, nitro, cyano, or trifluoromethyl;
• a heterocyclic radical selected from the group consisting of thienyl, furanyl, pyrrolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, pyrazolyl, imidazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, and pyridinyl, and N-oxides thereof;
• and a saturated heterocyclic radical selected from the group consisting of pyrrolidinyl, tetrahydrofuranyl, tetrahydrothienyl, isoxazolidinyl, oxazolidinyl, isothiazolidinyl, thiazolidinyl, pyrazolidinyl, imidazolidinyl, piperazinyl, and piperidinyl.