Monsanto Company

John P Chupp

Gerhard H Alt

Terry M Balthazor

Thomas E Neumann

Richard D Goodin

Michael J Miller

Audrey Y Ku

Thomas E Nickson

Lane A Clizbe

Len F Lee

James P Coleman

Bruce C Hamper

Harrison R Hakes

William F Goure

Jimmy W Worley

David James Mayonado

Richard H Wettach

John M Molyneaux

Barbara Heard Wells

Robert E Middlebrook

George R Harvey

The disclosure herein relates to the use of a variety of antidotal compounds to safen crop plants from the phytotoxicity of azolopyrimidine sulfonamide herbicides.

Safened herbicidal sulfonamide compositions

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

Heterocyclic- and carbocyclic- substituted benzoic acids and synthesis

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

Substituted 2,6-substituted 1,2- or 1,6-dihydro pyridine compounds

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.

Preparation of ortho-methyl anilines from ortho-amino benzyl sulfoxides

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.

Chemical intermediates and a process for their preparation

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.

Herbicidal 2-haloacetanilides

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.

N-((2-oxo-3(2H)benzothiazolyl)methyl)-2-chloroacetanilides

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.

Alkenyl acetamides

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.

Novel alkenyl acetamides and their use in the regulation of the natural

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.

Preparation of 2'-methyl-2-haloacetanilides

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.

Process for preparing substituted benzotrichloride compounds

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.

Preparation of substituted benzylic halides

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.

Substituted benzotrifluoride compounds as chemical intermediates and a

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. The aqueous phase separated after neutralization of the sulfilimine hydrochloride salt contains succinimide and/or sodium succinimide which may be converted by the action of chlorine to N-chlorosuccinimide which in turn may be recycled to the first step in the process.

Preparation of 2-(methylthiomethyl)-6-(trifluoromethyl)aniline from

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.

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Kirkwood, MO, United States of America

John P Chupp