Gaf Corporation

David E Graham

Louis Schneider

Joseph P Copes, Deceased

Herbicidal N-(haloacetyl-N-(N'-methylenepyrrolidonyl)-2-alkoxyanilines are provided in this invention having the formula: ##STR1## where R is alkyl of 1-6 carbon atoms, R' is hydrogen or lower alkyl of 1-3 carbon atoms, and X is halogen. The compounds of the present invention show good herbicidal activity against grassy weeds.

Herbicidal N-(haloacetyl)-N-(N'-methylenepyrrolidonyl)-2-alkoxyanilines

This invention relates to the control and/or eradication of Eumycotina type fungi is phanerogamia plants with one or more of the substituted carboxylic amides having the formula: ##STR1## wherein A is an organic radical of from 2 to 14 carbon atoms and is selected from the group consisting of hydroxyalkyl, hydroxyalkoxy, haloalkyl radicals and substituted alkylether radicals having the structure --R.sub.1 --O--R.sub.2 --, where R.sub.1 is alkylene of from 1 to 6 carbon atoms and R.sub.2 is alkyl of from 1 to 6 carbon atoms substituted with a hydroxy, carboxylate or halocarboxylate group; and wherein R is an acyclic alkyl radical, an alkenyl radical having one or more doubly bonded carbon atoms, a mono- or di- fluorinated benzyl radical or a mono- or di- chlorinated benzyl radical, said R radical containing from 4 to 20 carbon atoms. The invention also relates to a method of using a fungicidal amount of said carboxylic acid amide or carboxylic amide mixtures on phanerogamia plants for control or eradication of Eumycotina infection.

Hydroxyalkyl amides as fungicides to eumycotina in phanerogamia plant

Herbicidal compounds having the formula: ##STR1## where R is alkyl having 1-6 carbon atoms, alkenyl having 2-6 carbon atoms, cycloalkyl having 4-6 carbon atoms, unsubstituted or substituted with alkyl of 1-4 carbon atoms, or alkyleneoxyalkyl of 2-8 carbon atoms,

Herbicidal

This invention relates to an improved process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines which are useful intermediates in the synthesis of agricultural herbicides. This process of the invention comprises reacting a 2-substituted aniline with N-chloromethylpyrrolidone at about room temperature in the presence of an acid acceptor. Such room temperature alkylation of the aniline prevents excessive side reactions, particularly with a substituent in the 2-position of the aniline, such as an alkenyl group, which is sensitive to alkylating agents which require excessive heating to effective the condensation reaction.

Process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines

This invention relates to a process for making N-(N'-methylenepyrrolidonyl)-2-substituted anilines in high yield. The products are useful intermediates in the synthesis of herbicides. The process comprises reacting substantially equivalent molar concentrations of a 2-substituted aniline, as defined herein, with N-methylolpyrrolidone in an aromatic hydrocarbon solvent in the absence of an acid or base catalyst at a reflux temperature of 80.degree.-140.degree. C. while simultaneously and continuously distilling out from the reaction mixture an azeotrope consisting essentially of water and solvent until substantially all the water produced during the reaction has been removed thereby, and, thereafter, crystallizing the product from the remaining solution.

This invention relates to novel N-(N'-methylenepyrrolidonyl)-2-substituted anilines which are useful intermediates in the synthesis of herbicides. The intermediate compounds of the invention have the formula: ##STR1## Where R is alkyl, C.sub.1 -C.sub.6, alkenyl, C.sub.3 -C.sub.5, alkyleneoxyalkyl, --(CH.sub.2).sub.n OR', where n=1-3, and R' is alkyl, C.sub.1 -C.sub.3, and cycloalkyl, ##STR2## where n'=0-3, R' is hydrogen or alkyl, C.sub.1 -C.sub.3, and,

N-(N'-Methylenepyrrolidonyl)-2-substituted anilines

This invention relates to the control and/or eradication of Eumycotina type fungi in phanerogamia plants with one or more of the substituted carboxylic amides having the formula: ##STR1## wherein A is an organic radical of from 2 to 14 carbon atoms and is selected from the group consisting of hydroxyalkyl, hydroxyalkoxy, haloalkyl radicals and substituted alkylether radicals having the structure --R.sub.1 --O--R.sub.2 --, where R.sub.1 is alkylene of from 1 to 6 carbon atoms and R.sub.2 is alkyl of from 1 to 6 carbon atoms substituted with a hydroxy, carboxylate or halocarboxylate group; and wherein R is an acyclic alkyl radical, an alkenyl radical having one or more doubly bonded carbon atoms, a mono- or di- fluorinated benzyl radical or a mono- or di- chlorinated benzyl radical, said R radical containing from 4 to 20 carbon atoms. The invention also relates to a method of using a fungicidal amount of said carboxylic acid amide or carboxylic amide mixtures on phanerogamia plants for control or eradication of Eumycotina infection.

Carboxylic amides as fungicides to eumycotina in phanerogamia plant life

Herbicidal N-(haloacetyl)-N-(N'-methylenepyrrolidonyl)-2-alkoxyanilines are provided in this invention having the formula: ##STR1## where R is alkyl of 1-6 carbon atoms, R' is hydrogen or lower alkyl of 1-3 carbon atoms, and X is halogen. Another feature of the invention is the provision of N-(N'-methylenepyrrolidone)-2-alkoxyaniline or intermediates useful in making such herbicides. These intermediates are prepared by reaction of a 2-alkoxyaniline with an N-methylolpyrrolidone or an N-halomethylenepyrrolidone. The herbicide product than is obtained by acylation of the intermediate with a haloacetyl halide. The compounds of the present invention show good herbicidal activity against grassy weeds.

Herbicidal compounds having the formula: ##STR1## where n is 1-3,

Herbicidal n-(haloacetyl)-n-(n-methylene

The invention provides broad spectrum herbicidal diacylimide compositions which include compounds having the formula: ##STR1## where R and R' are selected from alkyl, alkenyl, haloalkyl and haloalkenyl having from 1-5 carbon atoms, being the same or different groups. The compositions of this invention show excellent agricultural herbicidal activity, particularly against foxtail millet, Japanese millet, crabgrass and pigweed, and aquatic herbicidal activity against lower and higher submerged aquatic plants.

Broad spectrum herbicidal diacylimide compositions

The invention provides broad spectrum herbicidal diacylimide compositions which include compounds having the formula: ##STR1## where R and R' are selected from alkyl, alkenyl, haloalkyl and haloalkenyl having from 1-5 carbon atoms, being the same or different groups. The compositions of this invention show excellent agricultural herbicidal activity, particularly against foxtail millet, Japanese millet, crabgrass and pigweed, and aquatic herbicidal activity against lower and higher submerged aquatic plants. The diacylimide compounds generally are prepared by reacting a suitable amide with an acyl halide. The acyl halide precursor may be prepared, if necessary, from the corresponding acid by reaction with a suitable halogenating agent, such as thionyl chloride. Similarly, a given amide may be readily prepared, for example, from the corresponding acyl halide by reaction with ammonia.

Aquatic herbicidal diacylimide compositions

Herbicidal compounds having the formula: ##STR1## where N=0-3,

Herbicidal N-(haloacetyl)-N'-methylenepyrrolidonyl)-2-cycloalkoxyanilines

Insecticidal N-acyl-N-(N'-methylenepyrrolidonyl)dialkylanilines having the formula: ##STR1## where R.sub.1 and R.sub.2 are both lower alkyl, and R is alkyl, alkenyl or haloalkenyl. Are prepared by two-step process involving reaction of 2,5-dialkylaniline with N-methylolpyrrolidone followed by acylation. The compounds of the present invention show good insecticidal activity against the Mexican bean beetle.

Insecticidal N-methylpyrrolidinonylacetanilides

The invention provides broad spectrum fungicidal diacylimide compositions which include compounds having the formula: ##STR1## where R and R' are selected from alkyl, alkenyl, haloalkyl and haloalkenyl having from 1-5 carbon atoms, being the same or different groups. The compositions of this invention show excellent agricultural fungicidal activity, particularly against bean rust, rice spot, tomato blight and other agricultural pathogens. The diacylimide compounds generally are prepared by reacting a suitable amide with an acyl halide. The acyl halide precursor may be prepared, if necessary, from the corresponding acid by reaction with a suitable halogenating agent, such as thionyl chloride. Similarly, a given amide may be readily prepared, for example, from the corresponding acyl halide by reaction with ammonia.

Broad spectrum fungicidal diacylimide compositions

In accordance with the sought-after features of an improved process for the preparation of Dimilin, there is provided herein a process which comprises first extracting 2,6-difluorobenzamide from an aqueous acid solution with a selective solvent which is acid-stable and water-insoluble. The extract then is condensed in situ with p-chlorophenyl isocyanate at an elevated temperature to form the desired product. The selective solvent preferably has a boiling point at the reaction temperature, preferably about 120.degree.-170.degree. C. Finally, the product is crystallized from the selective solvent.

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Westfield, NJ, United States of America

David E Graham