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Synthesis, Characterization, of 2H-3-Aryl-3, 4-Dihydro-1,3-Chlorobenzoxazine Derivatives of Benzoxazoline, antimicrobial activity and PC model Computational Studies

Author Affiliations

  • 1Department of Chemistry, Dr. H.S. Gour Central University Sagar, MP, 470 003, INDIA

Res.J.chem.sci., Volume 4, Issue (12), Pages 13-20, December,18 (2014)

Abstract

The invention comprises benzoxazole-2-carboxylic acid derivatives of the general formula wherein R represents a chlorine atom or an alkyl radical containing 1 to 4 carbon atoms, n is O or an integer of 1 to 4, and Y represents -OR1 or -NR112, wherein R1 represents an alkyl, aralkyl, cycloalkyl, aryl or chloroaryl radical and R11 represents a hydrogen atom or an alkyl, aralkyl or cycloalkyl radical, or -NR112 represents a heterocyclic ring. They may be prepared by causing a 3-chlorobenzoxazine-(1,4)-one-(2) of the general formula to react with ammonia, a strong basic primary or secondary amine, an alcohol, a phenol or a chlorophenol in the presence of an acid binding agent.; The reaction is expediently performed in an inert organic solvent or diluent at -30 DEG to + 200 DEG C. and when one of the reactants is an alcohol it can advantageously be used in excess as the diluent. Specified acid binding agents are the alkali metal and alkaline earth metal hydroxides, carbonates and bicarbonates, but in the case of the reaction with ammonia or an amine an excess thereof can be used instead of the binding agent.; The compounds of the invention may be isolated from the reaction mixture, which may contain the corresponding 3-substituted-benzoxazine-(1,4)-ones-(2) as by-products (see Specification 1,008,266), by, for example, fractional crystallization or preparative chromatography. ALSO:Herbicidal compositions comprise benzoxazole-2-carboxylic acid derivatives of the general formula wherein R represents a chloric atom or an alkyl radical containing 1 to 4 carbon atoms, n is 0 or an integer of 1 to 4, and 7 represents -OR1 or -NR112, where in R1 represents an alkyl, aralkyl, cycloalkyl, aryl or chloroaryl radical and R11 represents a hydrogen atom or an alkyl, aralkyl or cycloalkyl radical, or -NR112 represents a heterocyclic ring.; The compositions may be in the form of p emulsifiable concentrates, spray powders, pastes, soluble powders, dusts or granulates and contain 0.1 to 95% by weight of the active compounds.

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