E.i. Dupont De Nemours and Company

Degussa Aktiengesellschaft

Eric Deguyon Taylor

Karlheinz Drauz

Viacheslav Alexandrovich Petrov

Christoph Weckbecker

Steven Henry Swearingen

Balreddy Kamireddy

Anne Vogt

Matthias Schaeffer

A method for preparing a fused oxazinone is disclosed in which (1) a carboxylic acid is contacted with a sulfonyl chloride in the presence of an optionally substituted pyridine compound, the nominal mole ratio of sulfonyl chloride to carboxylic acid being from about 0.75 to 1.5; (2) the mixture prepared in (1) is contacted with an ortho-amino aromatic carboxylic acid in the presence of an optionally substituted pyridine compound, the nominal mole ratio of the ortho-amino aromatic carboxylic acid to carboxylic acid charged in (1) being from about 0.8 to 1.2; and (3) additional sulfonyl chloride is added to the mixture prepared in (2), the nominal mole ratio of additional sulfonyl chloride added in (3) to carboxylic acid charged in (1) being at least about 0.5. Also disclosed is a method for preparing a compound of Formula III, using a compound of Formula 1a that is characterized by preparing the fused oxazinone of Formula 1a by the method above, using a compound of the formula LS(O)Cl as the sulfonyl chloride, a compound of Formula 2' as the carboxylic acid, and a compound of Formula 5&#x2032; as the ortho-amino aromatic carboxylic acid (FORMULA 1a) (FORMULA III) (FORMULA 2&#x2032;) (FORMULA 5&#x2032;) wherein L, X, Y and Rthrough Rare as defined in the disclosure 

Method for preparing fused oxazinones from ortho-amino aromatic carboxylic acid and carboxylic acid in the presence of a sulfonyl chloride and pyridine

N-arylsulfonamide and pyrrolidinecarboxylic acid intermediates, and their use for the preparation of herbicidal 1,3-dioxo-1h-pyrrolo&lsqb;1,2-c&rsqb;imidazole derivatives

N-arylsulfonamide- and pyrrolidinecarboxylic acid intermediates, and their use for the preparation of herbicidal 1,3-dioxo-1h-pyrrolo&lsqb;1,2-c&rsqb;imidazole derivatives

The invention relates to certain 6-amino-substituted 2-pyridinesulfonylureas, intermediates thereof, and compositions and methods of their use.

Herbicidal pyridine sulfonylureas

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Wilmington, DE, United States of America

Eric Deguyon Taylor