Dow Agrosciences LLC

The Dow Chemical Company

Dow Global Technolgoies LLC

Dowelanco

Corteva Agriscience LLC

Timothy J Adaway

David E Podhorez

Larry D Kershner

Douglas L Pearson

Donald A Tomalia

Gary A Roth

Weishi W Wu

David Craig Molzahn

John Wesley Hull, Jr

Andrew S Kende

Jon A Orvik

Douglas Bland

Norman R Pearson

Anthony P Haag

Douglas C Greminger

Jimmy J Tai

Michael Allen Gonzalez

James P Easterly, Jr

Michael Lee Trippeer

Matthew J Jansma

Harold G Fravel, Jr

A process for the alkylation of picolinamides with substituted chloroacylals to produce a structure of Formula (III), wherein the reaction is performed in the presence of a phase-transfer catalyst and an inorganic halide co-catalyst. 

Alkylation of picolinamides with substituted chloroacylals utilizing a crown ether catalyst

Methods of producing a sulfilimine compound, such as N-cyano-S-methyl-S-[1-(6-trifluoromethyl-3-pyridinyl)ethyl]sulfilimine or other substituted sulfilimine compound. The method includes combining a sulfide compound, cyanamide, a hypochlorite compound, and a base, and oxidizing the sulfide compound to form the sulfilimine compound. The sulfide compound may include a 2-trifluoromethyl-5-(1-substituted)alkyl-thiopyridine compound. The base may include sodium hydroxide. A buffer, such as a phosphate buffer, may, optionally, be used in the reaction.

Methods of producing sulfilimine compounds

Butadiene copolymers are brominated using certain quaternary ammonium tribromides as the brominating agent in a first step, and then with elemental bromine in a second bromination step. The bromination process proceeds easily under mild conditions, and produces a brominated product that has excellent thermal stability. The bromination proceeds to high conversions in shorter reaction times, when the bromination is performed using only the first bromination step.

Two-step process for brominating butadiene copolymers

Cyano-substituted sulfilimines and sulfoximines are produced efficiently and in high yield from the corresponding sulfides by reaction with cyanamide and hypochlorite.

Process for the preparation of certain substituted sulfilimines

Spinetoram is selectively produced in excellent yields by hydrogenating a mixture of 3'-O-ethyl spinosyn J and 3&#x2032;-O-ethyl spinosyn L in a water miscible organic solvent using hydrogen gas and a heterogeneous catalyst.

Selective reduction of spinosyn factors Et-J and Et-L to spinetoram

A method for preparing a composition of the formulain a yield greater than 50% where Ris C 1-20 comprising the steps of combining fluorene or dibromo flourene, an excess of alkali metal hydroxide and a halogenated alkyl in the presence of a phase transfer catalyst but in the absence of a polar aprotic solvent; heating the combination; and separating the dialkylated fluorene or dialylated dibromo fluorene. If the flourene is not brominated prior to alkylation, the dialkylated fluorene is then brominated.

Method for producing substituted fluorene monomers

Chlorosulfonyl substituted aromatic heterocyclic compounds, such as 2-chlorosulfonyl[1,2,4]triazolo[1,5-c]pyrimidine compounds, were prepared in good yield by chloroxidation of di(aromatic heterocyclyl) disulfide compounds in a medium containing water, a water-immiscible organic solvent, and a phase transfer catalyst, such at tetrabutylammonium chloride.

Process for heterocyclic sulfonyl chloride compounds

N-(substituted aryl)�1,2,4!triazoloazinesulfonamide compounds, such as N-(2,6-difluorophenyl)-8-fluoro-5-methoxy�1,2,4!triazolo�1,5-c!pyrimidine- 2-sulfonamide, were prepared at a good reaction rate and in good yield by the reaction of a chlorosulfonyl�1,2,4!triazoloazine compound, such as 2-chlorosulfonyl-8-fluoro-5-methoxy�1,2,4!triazolo�1,5-c!pyrimidine, and an arylamine compound, such as 2,6-difluoroaniline, in an organic medium containing a relatively acidic alcohol, such as propylene glycol or 2,2,2-trifluoroethanol.

Preparation of n-arylarylsulfonamide compounds

3,3,5-Trichloroglutarimide is prepared by combining 4-cyano-2,2,4-trichlorobutanoyl chloride with water in an inert organic solvent at a temperature between about 20.degree. C. and about 50.degree. C. to obtain a mixture of 3,3,5-trichloroglutarimide and 3,3,5,6-tetrachloro-5,6-dihydropyridin-2-one. The 3,3,5,6-tetrachloro-5,6-dihydropyridin-2-one is then heated in the presence of water and inert organic solvent to between about 90.degree. C. and about 100.degree. C. to convert the 3,3,5,6-tetrachloro-5,6-dihydropyridin-2-one to 3,3,5-trichloroglutarimide.

Process for the preparation of 3,3,5-trichloroglutarimide

A method for preparing substituted phenoxyphenols which are useful in the preparation of herbicidal (phenoxyphenoxy)propionates is disclosed. The process involves the oxidation of substituted phenoxyphenones to the corresponding phenoxyphenyl esters and their conversion to the desired phenoxyphenol. Novel intermediates for the process are similarly disclosed.

Phenoxyphenoxypropionates, intermediates thereof and methods of

A process for preparing O-alkylated halopyridinate compounds is described. The process does not require the use of added organic solvents.

Catalyzed alkylation of halopyridinates in the absence of added organic

An improved method of preparing aryloxyphenoxy propanoic acid esters is disclosed. Low-water levels and low temperatures increase the yield and decrease by-product formation. A hindered non-nucleophilic phenol, which is converted in situ to the phenate form, is added to the reaction mixture to drive the reaction to 99+% conversion.

Method of preparing esters of aryloxyphenoxy propanoic acid

A water-in-oil emulsion of a water-soluble polymer such as acrylamide/acrylic acid copolymer having improved invertibility is prepared by (1) adding a portion of an inverting surfactant such as sorbitan trioleate having 20 polyoxyethylene units to a water-in-oil emulsion of water-soluble monomer, (2) polymerizing the monomer and (3) adding a remaining amount of inverting surfactant to the emulsion.

Self-inverting water-in-oil emulsions of water-soluble polymers

The level of residual 2-isopropenyl-2-oxazoline monomer in polymers prepared therefrom can be reduced by reaction of the protonated salt of the monomer with a variety of nucleophiles. The products of the reaction with the monomer are much less toxic than the 2-isopropenyl-2-oxazoline and the utility of the polymer is thereby enhanced. The reaction product of 2-isopropenyl-2-oxazoline and H.sub.2 SO.sub.3 is itself novel and useful.

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Midland, MI, United States of America

Timothy J Adaway