Monsanto Company

Hakes, Harrison R.

Alt, Gerhard H.

Brinker, Ronald J.

Gerhard H Alt

John P Chupp

John E Franz

Harrison R Hakes

Lane A Clizbe

John K Pratt

Ronald Joseph Brinker

Terry M Balthazor

Robert W Street

James A Kloek

Gabriel H Srouji

James S Bannon

W Gary Phillips

The present invention relates to certain substituted 5-carboxanilidothiazoles and their use as fungicides.

Substituted thiazoles and their use as fungicides

2-(Dichloroacetyl)-3-substituted-1,2,3,4-tetrahydroisoquinoline compounds are antidotes for thiocarbamate, triazine-type and acetamide herbicides. These antidote compounds are especially effective in safening acetamide herbicides used to control grassy and broadleaf weeds in corn.

2-(Dichloroacetyl)-3-substituted-1,2,3,4-tetrahydroisoquinolines as

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 sugarbeets. The herbicides herein are particularly effective against annual grasses, including hard-to-kill narrowleaf weeds such as blackgrass, wild oats, and downy brome and other prevalent grasses such as yellow foxtail, barnyardgrass, crabgrass, annual rye, etc.

Herbicidal 2-haloacetanilides

Haloacyl 1-substituted-1,2,3,4-tetrahydroisoquinoline compounds are antidotes for thiocarbamate, triazine-type and acetamide herbicides. These antidote compounds are especially effective in safening acetamide herbicides used to control grassy and broadleaf weeds in corn.

Haloacyl 1-substituted-1,2,3,4-tetrahydro-isoquinolines as herbicide

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 disclosure herein relates to 2-haloacetamides substituted on the amide nitrogen atom with certain specific alkenyl or heterocyclic aromatic radicals. These acetamides are useful as herbicides.

Herbicidal 2-haloacetamides

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

The disclosure herein relates to a group of N-alkoxymethyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly sorghum. Herbicides herein are particularly effective against hard-to-control weeds particularly seedling johnsongrass and/or shattercane, white proso millet, yellow nutsedge and redroot pigweed in addition to yellow foxtail, barnyardgrass and crabgrass.

The disclosure herein relates to 2-haloacetamides substituted on the amide nitrogen atom with certain specific alkenyl and alkoxyalkyl radicals. These acetamides are useful as herbicides.

The disclosure herein relates to a group of N-methyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly soybeans. The herbicides herein are particularly effective against the hard-to-kill annual weeds Texas panicum, itchgrass, wild proso millet, alexandergrass, shattercane and seedling johnsongrass.

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.

Nitro-methyl or ethyl substituted benzotrifluoride

The present disclosure relates to a new class of 2-haloacetanilide derivatives which are useful as herbicides. This disclosure further relates to herbicidal compositions containing such 2-haloacetanilides and to herbicidal methods of use employing such compounds and compositions.

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.

Substituted 2-alkylsulfonylalkyl nitrobenzenes and process for their

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.

Process for the in-solvent, in-situ generation of haloalkyl alkyl ethers

The disclosure herein relates to a group of N-alkyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly transplant rice. The herbicides herein are particularly effective against annual and perennial weeds commonly associated with rice.

Growing community of inventors

University City, MO, United States of America

Gerhard H Alt