Abstract: The disclosure herein relates to the title compounds and synthesis thereof by catalytic oxidation of the corresponding alkyl-substituted phenylheterocyclic or carboxylic compound.

Abstract: Disclosed herein are dihydropyridine dicarboxylic acid amide derivatives which are useful as herbicides, and herbicidal compositions and methods using same.

Abstract: This invention relates, in one of its aspects, to a process for the preparation of ortho-methyl anilines from ortho-amino benzyl sulfoxides. An ortho-amino benzyl sulfoxide is converted to an ortho-amino benzyl halide by reaction with a nonoxidizing acid halide and is converted to a stable quaternary salt by reaction with a tertiary amine in the presence of an alcohol. The quaternary salt may be cleaved by hydrogenation to form ortho-methyl anilines. Other aspects of the invention relate to novel intermediate quaternary salts and to a process for forming those quartenary salts.

Abstract: This invention pertains to chemical intermediates for a new class of 2-haloacetanilide herbicides and a process for preparation of these intermediates. The process generally involves nitration of substituted benzotrifluoride compounds.

Abstract: The disclosure herein pertains to 2-haloacetamides characterized by substitution on the nitrogen atom of certain heterocyclymethyl radicals and by substituted or unsubstituted cycloalkenyl or phenyl radicals and to a process for the preparation thereof. These compounds are useful as herbicides.

Abstract: The disclosure herein relates to a group of N-hydrocarbyloxymethyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly, corn and soybeans and other crops including cotton, peanuts, rape and bush beans. The herbicides herein are particularly effective against hard-to-kill perennial weeds such as quackgrass and nutsedges and are also effective against annual weeds.

Abstract: Compounds of the formula: ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen, halogen, C.sub.1-6 alkyl, or haloalkyl; R.sub.4 is hydrogen; C.sub.1-4 alkyl, alkenyl, alkoxy, haloalkyl; C.sub.1-2 alkylamino, C.sub.1-2 alkylthio, C.sub.2-4 cycloalkyl, C.sub.2-6 alkoxyalkyl, C.sub.2-6 alkylthiomethyl, amino, phenoxy, phenamino, or furan; and R.sub.5 is hydrogen or C.sub.1-4 alkyl, are useful to retard the growth of turf grass.

Abstract: The growth of turf grass can be retarded by applying to said turf grass an effective growth retarding amount of a compound of the formula: ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen, halogen, C.sub.1-6 alkyl, or haloalkyl; R.sub.4 is hydrogen; C.sub.1-4 alkyl, alkenyl, alkoxy, haloalkyl; C.sub.1-2 alkylamino, C.sub.1-2 alkylthio, C.sub.2-4 cycloalkyl, C.sub.2-6 alkoxyalkyl, C.sub.2-6 alkylthiomethyl, amino, phenoxy, phenamino, or furan; and R.sub.5 is hydrogen or C.sub.1-4 alkyl.

Abstract: This invention relates to a process for preparing 2'-methyl-2-haloacetanilides by selective catalytic hydrogenation of 2'-(halomethyl)-2-haloacetanilides. The 2'-(halomethyl)-2-haloacetanilides are initially prepared by reacting an ortho-(halomethyl) aniline or its anilinium salt with a haloacetyl halide.

Abstract: This invention pertains to a process for preparing substituted and unsubstituted benzotrichlorides. The process generally involves reacting the starting compound with a perchloroalkane with presence of base and a phase transfer catalyst.

Abstract: This invention pertains to processes for the preparation of nuclear substituted benzylic halides such as ortho-amino benzyl chlorides by reaction of substituted benzyl sulfoxides with nonoxidizing acid halides.

Abstract: This invention pertains to two substituted benzotrifluoride compounds useful as chemical intermediates for a new class of 2-haloacetanilide herbicides and a process for making these intermediates. The process generally involves nitration and reduction of the corresponding benzotrifluoride compound.

Abstract: This invention relates to a process for the preparation of 2-(methylthiomethyl)-6-(trifluoromethyl) aniline, [MTA], from ortho-aminobenzotrifluoride, (OABT), employing a single solvent transformation via a sulfilimine intermediate. A sulfilimine hydrochloride salt is prepared by the oxidative addition of dimethyl sulfide to OABT in the presence of N-chlorosuccinimide. Neutralization of the sulfilimine hydrochloride salt with aqueous sodium hydroxide followed by phase separation results in an organic phase containing free sulfilimine and an aqueous phase generally containing succinimide and/or sodium succinimide. In a preferred embodiment the phase separation is performed in such a manner to leave a catalytic amount of succinimide in the organic phase. The free sulfilimine catalytically rearranges at moderate temperatures in the presence of this succinimide catalyst to form MTA.

Abstract: orthoAlkyl-orthotrifluoromethyl-2-chloroacetanilides and related compounds are prepared by electrolytic reduction with sulfide cleavage of benzylsulfonium salts with requisite chloroacetylamino and trifluoromethyl substituents on the benzyl group. The compounds are useful as intermediates for conversion to herbicidal compounds.

Abstract: This invention relates to a process for the preparation of ortho-aminobenzotrifluoride (OABT) from benzotrifluoride (BTF). The process provides an overall route employing non-isolation of intermediates which can be run smoothly and which results in the preparation of OABT in high yields with less contamination. This process includes a catalytic halogenation step in which BTF is converted to meta-halo BTF and other mono and di-halo isomers of BTF followed by nitration in the same reaction vessel under conditions which do not favor nitration of the di-halo isomers of BTF to produce a mixture which predominates in 5-halo-2-nitro BTF. In the final step the 5-halo-2-nitro BTF present is reduced and hydrodehalogenated with H.sub.2 in the presence of a catalyst to form OABT. Recyclable BTF is also obtained from the final reaction.

Abstract: The invention herein pertains to nitro-methyl or ethyl substituted benzotrifluoride compounds useful as chemical intermediates and a process for their preparation. The chemical intermediates are useful for the preparation of substituted anilines which are precursors for a new class of 2-haloacetanilide herbicides.

Abstract: The disclosure herein relates to substituted 2-alkylsulfonylalkyl nitrobenzenes and a process for the preparation thereof. The compounds herein are useful as intermediates in the preparation of certain substituted anilines used as reactants in the preparation of 2-haloacetanilide herbicides.

Abstract: Various substituted ortho-alkyl anilines are prepared by electrolytic desulfurization of various benzyl sulfides, sulfoxides and sulfones, e.g. 2-methyl-6-trifluoromethylaniline is prepared from 2-amino-3-trifluoromethylbenzyl sulfides, sulfoxides and sulfones. The processes are conducted in concentrated aqueous quaternary ammonium hydroxide, as well as in aprotic media. The substituted anilines obtained are useful as intermediates for herbicide compounds.

Abstract: The present invention is directed to a process for the preparation of certain N-substituted-2-haloacetanilides via the reaction of a secondary 2-haloacetanilide with a haloalkyl ether, particularly, halomethyl ethers, which comprises forming the ether in situ by the in-solvent reaction of an alcohol, formaldehyde or other aldehyde and an acid halide to produce high purity haloalkyl ethers, while decreasing the concentration of undesirable bis by products, as for example bis(chloromethyl) ether. The ether formed in situ thereafter reacts with the secondary 2-haloacetanilide in the presence of a phase transfer catalyst and base to form the N-substituted-2-haloacetanilide.

Abstract: The disclosure herein relates to tertiary 2-haloacetamides substituted on the amide nitrogen atom with certain 1-cycloalken-1-yl, alkoxymethyl, alkylthiomethyl or acetamidomethyl radicals. These acetamides are useful as herbicides.