Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-Fluoropyridinium salts having trichloromethyl substituents are disclosed.

Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)-pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-fluoropyridinium salts having trichloromethyl substituents are disclosed.

Abstract: 2-Hydrocarbyl-3,6-dichloropyridines are prepared from dichloromethyl hydrocarbyl ketones and acrylonitrile in a two-step process involving an addition reaction under basic conditions to form intermediate 1,1-dichloro-3-cyanopropyl hydrocarbyl ketones and a subsequent cyclization reaction in the presence of hydrogen chloride. Thus, 3,6-dichloro-2-methylpyridine is prepared from 1,1-dichloro-2-propanone and acrylonitrile by the formation and further reaction of 4,4-dichloro-5-oxo-hexanenitrile. The intermediates and products are novel compounds useful in the preparation of herbicides and nitrification inhibitors.

Abstract: 2-Hydrocarbyl-3,6-dichloropyridines are prepared from dichloromethyl hydrocarbyl ketones and acrylonitrile in a two-step process involving an addition reaction under basic conditions to form intermediate 1,1-dichloro-3-cyanopropyl hydrocarbyl ketones and a subsequent cyclization reaction in the presence of hydrogen chloride. Thus, 3,6-dichloro-2-methylpyridine is prepared from 1,1-dichloro-2-propanone and acrylonitrile by the formation and further reaction of 4,4-dichloro-5-oxo-hexanenitrile. The intermediates and products are novel compounds useful in the preparation of herbicides and nitrification inhibitors.

Abstract: Symmetrical tetrachloropyridine is prepared by contacting chlorinated .beta.-(trichloromethyl)pyridines with chlorine in a liquid phase reaction in the presence of from 0.1 to 1.0 mole % of a catalyst.

Abstract: Symmetrical tetrachloropyridine is prepared by contacting chlorinated .beta.-(trichloromethyl)pyridines with chlorine in a liquid phase reaction in the presence of from 0.1 to 1.0 mole % of a catalyst.

Abstract: The relative amounts of 5,6-dichloro-2-(trichloromethyl)pyridine and 3,6-dichloro-2-(trichloromethyl)pyridine obtained in the chlorination of 2-chloro-6-(trichloromethyl)pyridine in the liquid phase at temperatures of about 160.degree. C. to about 220.degree. C. and in the presence of a metal halide catalyst, such as ferric chloride, are controlled by regulating the amount of hydrogen chloride present in the system, adding hydrogen chloride to obtain a mixture enriched in 5,6-dichloro-2-(trichloromethyl)pyridine or removing hydrogen chloride, usually by passing excess chlorine or an inert gas through the system, to obtain a mixture enriched in 3,6-dichloro-2-(trichloromethyl)pyridine.

Abstract: Novel methods for preparing 2-cyano-6-chloropyridines are disclosed. The compounds are useful as intermediates in preparing other intermediates or as intermediates directly used in making pesticides, especially herbicides.

Abstract: Trichloro- and tetrachloro(trichloromethyl)pyridines contaminated with hexachlorobenzene are converted to useful products containing acceptably low levels of hexachlorobenzene by chlorination under conditions of chlorinolysis to tetrachloro- and pentachloropyridine and then removing the hexachlorobenzene by distillation. For example, 2,3,6-trichloro-5-(trichloromethyl)pyridine contaminated with hexachlorobenzene is converted to 2,3,5,6-tetrachloropyridine containing less than 50 ppm hexachlorobenzene.

Abstract: Novel 2,3-bis((poly)chloromethyl)pyridines and 3,6-dichloro--2-(polychloromethyl)pyridines were obtained by vapor phase chlorination of 2,3-lutidine. Chlorination at about 350.degree. C. using a 14.4 sec. residence time and a chlorine to 2,3-lutidine mole ratio of about 6.8, for example, produced 2-(chloromethyl)-3-(dichloromethyl) pyridine, 3-(chloromethyl)-2-(dichloromethyl)pyridine, 2,3-bis(dichloromethyl)pyridine, 6-chloro-2,3-bis(dichloromethyl)pyridine, 3-(dichloromethyl)-2-(trichloromethyl)pyridine, 6-chloro-3-(dichloromethyl-2-(trichloromethyl)pyridine, 6-chloro-2-(dichloromethyl)-3-(trichloromethyl)pyridine, and 3,6-dichloro-2-(trichloromethyl)pyridine. The compounds are useful as starting materials for herbicides and pharmaceutical agents.

Abstract: Polychloropyridines containing chlorine substituents in the 2, 3, and 6 positions and, optionally, in the 4 and 5 positions, are prepared from polychloro-2,3-lutidines containing at least one chlorine substituent in each methyl group and, optionally, a chlorine substituent in the 6 position by liquid phase chlorination. Lewis acid metal halide catalysts are, optionally, employed. 2,3,5,6-Tetrachloropyridine is, accordingly, prepared by chlorination at about 200.degree. to about 260.degree. C. in the presence of ferric chloride catalyst of a mixture of polychloro-2,3-lutidines obtained by the vapor phase chlorination of 2,3-lutidine.

Abstract: The selective chlorination of 2-chloro-5-(trichloromethyl)pyridine in the 3-position is achieved by reacting 2-chloro-5-(trichloromethyl)pyridine in the liquid phase with an effective amount of Cl.sub.2 at an elevated pressure and elevated temperature in the absence of an added catalyst.

Abstract: Symmetrical tetrachloropyridine is prepared by contacting chlorinated .beta.-(trichloromethyl)pyridines with chlorine in a liquid phase reaction in the presence of from 0.1 to 1.0 mole % of a catalyst.

Abstract: A method is disclosed for preparing a chlorinated .beta.-methylpyridine by chlorinating a .beta.-methylpyridine compound with PCl.sub.5 in the presence of phenylphosphonic dichloride.

Abstract: Symmetrical tetrachloropyridine, pentachloropyridine and poly-chloro derivatives of 2-chloro-6-(trichloromethyl)pyridine are prepared by reacting a chloro-substituted (trichloromethyl)pyridine in the liquid state with chlorine at temperatures of from at least about 160.degree. C. and in the presence of an amount of a catalyst effective to catalyze the reaction.

Abstract: Pentachloropyridine and polychloro derivatives of 2-(trichloromethyl)pyridine are prepared by reacting 2,4-dichloro-6-(trichloromethyl)pyridine in the liquid state with chlorine at temperatures of from about 160.degree. C. in the presence of an amount of catalyst effective to catalyze the reaction.

Abstract: Substituted 7,8-dihydro-6H-(1,2,5)thiadiazolo(3',4'-5,6)pyrazino(2,3-b)(1,4)oxazine compounds useful as herbicides or fungicides are disclosed.

Abstract: Dichloropyrazino-oxazines of the formula ##STR1## wherein R is H or a C.sub.1 to C.sub.8 alkyl, alkenyl, cycloalkyl or cycloalkenyl radical, are disclosed. The compound in which R is H has utility as an intermediate for the compounds in which R is other than H. The latter compounds exhibit microbicidal, herbicidal or insecticidal activity. The compounds of the invention are readily prepared from tetrachloropyrazine and 2-aminoethanols of the formula R--NH--CH.sub.2 CH.sub.2 --OH.

Abstract: The title compound is readily prepared in good yield by the reaction of acetylacetone with ammonia in methanol. It has fungicidal and insecticidal properties and, by reason of the number and variety of functional groups it contains, should be useful as an intermediate.