The Dow Chemical Company

Honeywell International Inc.

Kalakota S Reddy

Charles D Gartner

Andreas Kanschik-Conradsen

George A Paul

Christian N Werner

David E Wallick

Warren L Treptow

Frank Nerenz

John K Swayze

Connie L Deford

Connie I Deford

Billy R Hardas

Thomas L Siddall

The present invention provides an improved phosphoramidite activator comprising a solution of 5-benzylmercaptotetrazole in acetonitrile and N-alkyimidazole. Further provided are improved methods of oligonucleotide synthesis wherein a phosphoramidite activator comprising a solution of 5-benzylmercaptotetrazole in acetonitrile and N-alkyimidazole is used to prepare internucleoside linkages.

Phosphoramidite activator for oligonucleotide synthesis

Provided are methods of producing phosphitylated compounds, including 3'-O-phosphoramidites, comprising the step of reacting a hydroxyl-containing compound with a phosphitylating agent in the presence of a phosphitylation activator selected from the group consisting of: (1) acid-base complexes derived from an amine base of Formula II wherein R, R, R, R, and Rare independently hydrogen, C&#x2013;Calkyl, C&#x2013;Ccycloalkyl, C&#x2013;Caryl, C&#x2013;Caralkyl, C&#x2013;Cheteroalkyl, or C&#x2013;Cheteroaryl, and at least one of R, R, R, R, and Ris not hydrogen; (2) zwitterionic amine complexes; and (3) combinations of two or more thereof, to produce a phosphitylated compound. Further provided are methods for purifying phosphitylated compounds comprising the steps of providing a phosphitylated compound in a solution solvent, contacting said phosphitylated compound with a precipitation solvent, and precipitating said phosphitylated compound.

Methods of producing phosphitylated compounds

Provided are methods of producing phosphitylated compounds, including 3'-O-phosphoramidites, comprising the step of reacting a hydroxyl-containing compound with a phosphitylating agent in the presence of a phosphitylation activator selected from the group consisting of: (1) acid-base complexes derived from an amine base of Formula Iwherein R, R, and Rare independently C-Calkyl, C-Ccycloalkyl, C-Caryl, C-Caralkyl, C-Cheteroalkyl, or C-Cheteroaryl, wherein any two adjacent R, R, and Rmay be connected to form a heterocyclic ring; (2) acid-base complexes derived from a diazabicyclo amine base; and (3) combinations of two or more thereof.

Phosphonic acid, (2-halo-2-cyanoethylenyl)-dialkylesters are prepared which correspond to the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently represent an alkyl group and X represents a halogen. These compounds have been found to exhibit antimicrobial activity in industrial and commercial applications and compositions containing these compounds are so employed.

Composition and use of phosphonic acid, (2-halo-2-cyanoethenyl)-dialkyl

Substituted 3-thio-2-propynenitriles are prepared which correspond to the formula:

Composition and use of substituted 3-thio-2-propynenitriles as

3-Thiocyano-2-halo-2-propenenitriles are prepared which correspond to the formula: ##STR1## wherein X is a halogen. These compounds have been found to exhibit a high degree of antimicrobial activity in industrial and commercial applications and compositions containing these compounds are so employed.

Composition and use of 3-thiocyano-2-halo-2-propenenitriles as

3-(2-Pyridinylthio-N-oxide, 2-halo-2-propenenitriles are prepared which correspond to the formula: ##STR1## wherein X represents a halogen. These compounds have been found to exhibit antimicrobial activity in industrial and commercial applications and compositions containing these compounds are so employed.

3-(2-pyridinylthio)-N-oxide, 2-halo-2-propenenitrile compounds useful as

Composition and use of substituted 3-thio-2-propynenitriles as an

The present invention is directed to a method of using a compound corresponding to the formula: ##STR1## as an antimicrobial agent comprising contacting a microorganism or a habitat thereof with an antimicrobially effective amount of the compound. This 3-iodo-2-chloro-2-propenenitrile compound has been found to exhibit a high degree of antimicrobial activity in industrial and commercial applications and compositions containing this compound are so employed. An antimicrobial composition comprising and a process for the preparation of the 3-iodo-2-chloro-2-propenenitrile compound are also disclosed.

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Midland, MI, United States of America

Kalakota S Reddy