The Dow Chemical Company

George A Burk

Christian T Goralski

Craig E Mixan

Charles A Wilson

R Garth Pews

Charles E Reineke

Brian G Witt

Kurt W Swogger

An alkyl .alpha.-cyanoacetate is reacted with ammonia in a glycol solvent medium to form cyanoacetamide. Advantageously and without requirement of separation of the formed cyanoacetamide in glycol solvent (even though the next step and entire procedure can optionally commence with pre-formed cyanoacetamide), 2,2-dibromo-3-nitrilopropionamide is formed in situ by treating the cyanoacetamide in glycol with an appropriate mixture of bromine and an alkali metal bromate at about 10.degree. C-40.degree. C. Excellent and stable antimicrobial compositions may then be prepared, as part of an overall integrated process by incorporating in the resultant 2,2-dibromo-3-nitrilopropionamide-containing reaction mass an appropriate quantity of paraformaldehyde or equivalent satisfactory stabilizer at a suitably adjusted pH level.

Preparation of cyanoacetamide and 2,2-dibromo-3-nitrilopropionamide

Aqueous antimicrobial compositions which comprise a halogenated amide antimicrobial, such as 2,2-dibromonitrilopropionamide, a water miscible organic solvent such as a straight chain polyalkylene glycol (e.g., polyethylene glycol 200) or an ether thereof (e.g., a mono- or di-lower alkyl and/or phenyl ether) and water are stabilized against decomposition of the halogenated amide antimicrobial by the addition of an acid or anhydride stabilizer such as acetic acid, glycolic acid, boric acid, ethylenediaminetetraacetic acid, succinic anhydride, etc. The compositions, so stabilized, exhibit reduced rates of decomposition of the halogenated amide antimicrobial relative to the corresponding non-stabilized aqueous compositions.

Stabilized aqueous antimicrobial composition

Aqueous antimicrobial compositions which comprise a halogenated amide antimicrobial, such as 2,2-dibromonitrilopropionamide, a water miscible organic solvent such as a straight chain polyalkylene glycol (e.g., polyethylene glycol 200) or an ether thereof (e.g., a mono- or di-lower alkyl and/or phenyl ether) and water and which have improved stability are obtained by ensuring that such compositions are substantially free of glycols having a molecular weight of less than about 70 and of salts of organic acids. The resulting improved compositions exhibit reduced rates of decomposition of the halogenated amide antimicrobial relative to the corresponding aqueous compositions containing salts of organic acids and/or glycols having a molecular weight of less than about 70.

Aqueous antimicrobial composition having improved stability

The novel compounds corresponding to the formula ##STR1## or of the formula ##STR2## wherein R is a thiadiazole radical. These compounds exhibit utility in the control and kill of bacteria and fungi.

Antimicrobial bis(5-nitro-2-thiazolyl)thioisothiazoles and thiadiazoles

Aqueous antimicrobial compositions which comprise a halogenated amide antimicrobial, such as 2,2-dibromonitrilopropionamide, a water miscible organic solvent such as a straight chain polyalkylene glycol (e.g., polyethylene glycol 200) or an ether thereof (e.g., a mono- or di- lower alkyl and/or phenyl ether) and water are stabilized against decomposition of the halogenated amide antimicrobial by the addition of a cyclic ether stabilizer such as tetrahydrofuran, tetrahydropyran, 1,4-dioxane, sym-trioxane, N-methyl morpholine, etc. The compositions, so stabilized, exhibit reduced rates of decomposition of the halogenated amide antimicrobial relative to the corresponding non-stabilized aqueous compositions.

Stabilized aqueous amide antimicrobial composition

Aqueous antimicrobial compositions which comprise a halogenated amide antimicrobial, such as 2,2-dibromonitrilopropionamide, a water miscible organic solvent such as a straight chain polyalkylene glycol (e.g., polyethylene glycol 200) or an ether thereof (e.g., a mono- or di-lower alkyl and/or phenyl ether) and water are stabilized against decomposition of the halogenated amide antimicrobial by the addition of a carbamoyl or sulfamoyl stabilizer, such as dimethyl formamide, sulfamide, urea, oxamide, biuret, caprolactam, succinimide, etc. The compositions, so stabilized, exhibit reduced rates of decomposition of the halogenated amide antimicrobial relative to the corresponding non-stabilized aqueous compositions.

Aqueous antimicrobial compositions which comprise a halogenated amide antimicrobial, such as 2,2-dibromonitrilopropionamide, a water miscible organic solvent such as a straight chain polyalkylene glycol (e.g., polyethylene glycol 200) or an ether thereof (e.g., a mono- or di- lower alkyl and/or phenyl ether) and water are stabilized against decomposition of the halogenated amide antimicrobial by the addition of an aldehyde stabilizer, such as formaldehyde, paraformaldehyde, N-formyl piperidine, vanillin, etc. The compositions so stabilized exhibit reduced rates of decomposition of the halogenated amide antimicrobial relative to the corresponding non-stabilized aqueous compositions.

Aqueous antimicrobial compositions which comprise a halogenated amide antimicrobial, such as 2,2-dibromonitrilopropionamide, a water miscible organic solvent such as a straight chain polyalkylene glycol (e.g., polyethylene glycol 200) or an ether thereof (e.g., a mono- or di-lower alkyl and/or phenyl ether) and water are stabilized against decomposition of the halogenated amide antimicrobial by the addition of an azine or nitrile stabilizer, such as s-triazine-2,4,6-triol (i.e., cyanuric acid), 2-chloro-4,6-(ethylamino)-s-triazine, succinonitrile, cyanoguanadine, etc. The compositions, so stabilized, exhibit reduced rates of decomposition of the halogenated amide antimicrobial relative to the corresponding non-stabilized aqueous compositions.

Aqueous antimicrobial compositions which comprise a halogenated amide antimicrobial, such as 2,2-dibromonitrilopropionamide, a water miscible organic solvent such as a straight chain polyalkylene glycol (e.g., polyethylene glycol 200) or an ether thereof (e.g., a mono- or di- lower alkyl and/or phenyl ether) and water are stabilized against decomposition of the halogenated amide antimicrobial by the addition of a quaternary salt stabilizer, such as methyl triphenyl phosphonium bromide, benzyl triethyl ammonium bromide, etc. The compositions, so stabilized, exhibit reduced rates of decomposition of the halogenated amide antimicrobial relative to the corresponding non-stabilized aqueous compositions.

The novel compounds corresponding to the formula ##STR1## wherein x is 3 or 4. These compounds exhibit utility in the control and kill of bacteria and fungi.

((5-Nitro-2-thiazolyl)thio)polyhalogenated pyridines

Novel compounds, i.e. 3,5-bis(chloromethylthio)-4-cyanoisothiazole; 2,5-bis(chloromethylthio)-1,3,4-thiadiazole; and 3,5-bis(chloromethylthio)-1,2,4-thiadiazole are prepared by reacting an alkali metal aryl mercaptide with bromochloromethane in the presence of a quaternary ammonium salt. These novel compounds have microbiological activity and are also useful as intermediates in the preparation of the corresponding thiocyanomethylthio compounds which have antimicrobial activity.

3,5-Bis(chloromethylthio)-4-cyanoisothiazole

Compounds are prepared corresponding to the formula ##STR1## WHEREIN EACH R represents alkyl of 1 to 4 carbon atoms. These compounds can be employed as starting materials for preparing 3,4,5-trichloro-N,N-di(loweralkyl)-2-(thiomethylthiocyanato)benzenesulfona mides which are useful as antimicrobial agents.

3,4,5-Trichloro-N,N-Di(loweralkyl)-2-((chlor

The compound of this invention is prepared by reacting phenol as such or as its alkali metal phenate with dichlorodifluoroethylene to form 2,2-dichloro-1,1-difluoroethoxybenzene and reacting the latter with chlorosulfonic acid and recovering the reaction product. The compound of this invention, when reacted with acrylonitrile gives the antimicrobial compound, 2-chloro-3-(4-(2,2-dichloro-1,1-difluoroethoxy)phenyl)sulfonyl)propanenitr ile.

4-(2,2-Dichloro-1,1-difluoroethoxybenzene) sulfonyl chloride and its

Bis(chloromethylthio)thiadiazoles

The compound 3-((4-(2,2-dichloro-1,1-difluoroethoxy)-2-methyl-5-nitrophenyl)sulfonyl)-2 -propenenitrile. The compound has antimicrobial activity.

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Bay City, MI, United States of America

George A Burk