Eli Lilly and Company

Riaz F Abdulla

Jack G Samaritoni

Donald C DeLong

Quentin F Soper

Norman H Terando

Kenneth H Fuhr

Lawrence A Morgan

This invention provides antiviral pyridazinyl hydrazones of the formula ##STR1## wherein when taken singly, R is H, CH.sub.3 or C.sub.2 H.sub.5 ; and R.sup.1 is thienyl, halothienyl, pyridyl, methylthienyl, furyl, indolyl, tolyl, xylyl, biphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, 1-adamantyl and, when R is other than H, methyl; R and R.sup.1 taken together form a 2-adamantindinyl group; and R.sup.3 is a C.sub.4 -C.sub.6 tertiary alkyl group attached through a tertiary carbon to the pyridazine ring, such as t-butyl, 1,1-dimethylethyl, 1,1-dimethylpropyl, or 1-methyl-1-ethylpropyl, and mineral acid addition salts thereof.

Antiviral pyridazine hydrazones

This invention describes noval pyridazinylurea compounds, which are useful as herbicides.

Pyridazinylurea compounds and methods of use as herbicides

This invention describes novel pyridazinylimidazolidinone compounds, which are useful as herbicides.

Herbicidal pyridazinylimidazolidinone compounds

This invention discloses novel pyridinylimidazolidinone compounds, which are useful as herbicides.

Pyridinylimidazolidinone compounds

A class of 6-t-alkyl-3-pyridazinones are prepared from 3-t-alkanoyl-2-propenoic acids by irradiation with strong light and reaction with hydrazine.

Synthesis of 6-t-alkyl-3-pyridazinones

Acetyl-tertiary-alkanes are prepared by hydrolytic decarboxylation of tertiary-alkanoylacetonitriles with hydrochloric acid.

Synthesis of acetyl-T-alkanes

A series of novel 1-alkyl-3-acyl-5-substituted-phenyl-4(1H)-pyridinones are herbicides, particularly useful in the culture of cotton.

3-Acyl-5-phenyl-4(1H)-pyridinones and their use as herbicides

A process or acylating or sulfenylating 1-amino-2-phenyl-1-butene-3-ones to prepare the corresponding 4-acyl or 4-substituted-thio compounds provides intermediates useful for preparing herbicides.

Acylation or sulfenylation process

3,4-Dihydro-3-oxoquinoxalines carrying a carboxylic acid or ester function in the 2 position, used as antiviral agents, particularly against influenza virus, both A and B strains.

Treatment of influenza with

Salts of 6,7-dihalo-3,4-dihydro-3-oxo-2-quinoxaline carboxylic acids and hindered amines, useful in combating influenza A and B.

Salts of dihalo-3,4-dihydro-3-oxo-2-quinoxaline carboxylic acids and

.alpha.,.beta.-Unsaturated ketones and aldehydes, together with a method of preparation thereof which comprises reacting aldehydes and cyclic and acyclic ketones possessing a methyl or methylene group .alpha.- to the carbonyl function with N,N-dialkylformamide dialkyl acetal to yield the corresponding enaminoketones and enaminoaldehydes, which enaminoketones and enaminoaldehydes are allowed to react with alkyllithium reagents to yield the corresponding nitrogen-free 2-alkylidene ketones and 2-alkylidene aldehydes.

.alpha.,.beta.-Unsaturated ketones and aldehydes and method of

Benzoylureas are prepared from a benzamide, an alkyllithium, a phenyl chloroformate, and an amine. Two reaction sequences are described. The benzoylureas obtained by the process are useful as insecticides.

Preparation of benzoylureas

A class of herbicidal 3-phenyl-5-substituted-4(1H)-pyridones are prepared from .beta.-aminostyrenes by reaction with bromoacetyl bromide to form an .alpha.-bromoacetyl-.beta.-aminostyrene which is reacted with an anion to form a .alpha.-substituted acetyl-.beta.-aminostyrene which is then cyclized to the pyridone by formylation and reaction with a primary amine.

Method for the preparation of 3-phenyl-5-substituted-4(1H)-pyridones

A class of 4-amino-3,3-dimethyl-1-phenyl-2-azetidinones reduce the vigor of unwanted herbaceous plants to which the compounds are applied. The compounds are effective when applied either preemergence or postemergence at rates from about 2 to about 20 kg./ha.

Herbicidal use of 4-amino-3,3-dimethyl-1-phenyl-2-azetidinones

A series of 3,5-diphenyl-4(1H)-pyridazinones are synthesized by a two-step process, both steps of which are new. In the first step, a phenylglyoxyloyl halide is reacted with a styrylamine in the presence of a base to form a 1-amino-2,4-diphenyl-1-buten-3,4-dione. In the second step, the enaminoketone formed in the first step is reacted with hydrazine or an alkylhydrazine to form the pyridazinone. Both steps of the reaction proceed in good yields at temperatures in the range of from about 0.degree. C. to about 40.degree. C. in the common reaction solvents.

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Greenfield, IN, United States of America

Riaz F Abdulla