The Dow Chemical Company

Craig E Mixan

Christian T Goralski

George A Burk

R Garth Pews

Charles A Wilson

John A Werner

Preparation of 2,3-dichloro-5-trichloromethylpyridine in high yields and purity by chlorinating 2-chloro-5-trichloromethylpyridine at 70.degree. to 250.degree. C. with chlorine in the presence of a catalyst containing one or more molybdenum, tungsten or ruthenium compounds.

Preparation of 2,3-dichloro-5-trichloromethylpyridine

Ether cleavage in transesterifications of pyridyloxyphenoxy alkanoic acid compounds is reduced by employing titanium compounds as catalysts.

Titanium catalyzed transesterification

The novel compound (1,4)Dithiino(2,3-b) (1,2,5)-thiadiazole(3,4-e)pyrazine-6,7-dicarbonitrile, its method of use in the control and kill of bacteria and fungi, and compositions containing the novel compound as the active ingredient therein are claimed.

(1,4)Dithiino(2,3-b)(1,2,5)-thiadiazole(3,4-e)pyrazine-6,7-dicarbonitrile

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

Novel 1,4-Dithiinopyrazinetetracarbonitriles are disclosed. Their method of use in the control and kill of bacteria and fungi, and compositions containing the novel compounds as the active ingredients therein are claimed.

1,4-Dithiino pyrazine tetracarbonitriles

Novel compounds corresponding to the formula ##STR1## wherein n, n' and x are, individually, 0 or 1. These compounds exhibit utility in the control and kill of bacteria and fungi.

((5-Nitro-2-thiazolyl)thio) and ((5-nitro-2-thiazolyl)sulfinyl)pyrazines

Novel (1,4)Dithiino(2,3-b)(1,3)thiazole-(4,5-e)pyrazine-6,7-dicarbonitriles, the ir method of use in the control and kill of bacteria and fungi, and compositions containing the novel compounds as the active ingredients therein are claimed.

(1,4)Dithiino(2,3-b)(1,3)thiazole-(4,5-e)pyrazine-6,7-dicarbonitriles

Processes for preventing marine fouling which employ either p-Dithiino(2,3-b)pyrazine-2,3-dicarbonitrile, 1,3-Dithiolo(4,5-b)pyrazin-2-ylidene-propanedinitrile or mixtures thereof.

Marine antifoulant processes

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

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

Compounds are prepared which correspond to the formula ##STR1## wherein n represents an integer of 0 to 3; p represents an integer of 0 to 2 and the sum of n + p is an integer of 0 to 3; and r is 0 or 1. These compounds have been found to be active as pesticides and find particular usage as fungicides, bactericides, nematocides and herbicides.

Cyanatothiomethylthio pyrazines

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

3-((4-(2,2-Dichlor

The novel compounds corresponding to the formula ##STR1## wherein R is either H or CX.sub.3, with each X substituent being individually selected from the group consisting of H and X' wherein X' is either F or Cl, are prepared by reacting di(sodiomercapto)methylenemalononitrile with the corresponding 5,6-dihalothiazolo(4,5-b)pyrazine in dimethylformamide as a reaction medium at a temperature between about 0.degree. C and about 60.degree. C until the reaction is substantially complete. The novel compounds of the present invention have antimicrobial activity.

(1,3)Dithiolo-(4,5-b)thiazolo(4',5'-e)pyrazin-2-ylidene-propanedinitriles

(1,3-Dithiolo(4,5-b) (1,2,5)thiadiazolo(3',4'-e)pyrazin-6-ylidene)-propanedinitrile is prepared by reacting di(sodiomercapto)methylenemalononitrile with 5,6-dichloro-1,2,5-thiadiazole(3,4-b)pyrazine in dimethylformamide as reaction medium at a temperature between about 20.degree. C and about 60.degree. C until the reaction is substantially complete. The reaction product has antimicrobial utility.

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Midland, MI, United States of America

Craig E Mixan