The Dow Chemical Company

Dowelanco

Michael G Smith

James M Renga

Patricia G Ray

Brian K Riley

Charles Marlowe

Robert J Ehr

Charles K Bon

Wendy S Jacks

William C Lo

Aylin H Gulbenkian

Aylin H Gulkenkian

2-(Phenoxy or phenylthio)-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoic acid compounds, such as ethyl 2-(2-fluorophenoxy)-2-(4,6-dimethylpyrimidin-2-yloxy)-acetate, were prepared by the reaction of a phenol or thiophenol compound with a 2-chloro-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoate ester compound or by the reaction of a pyrimidinol or 1,3,5-triazinol with a 2-bromo-2-(phenoxy or phenylthio)alkanoate ester. These compounds, and, especially, agriculturally acceptable salts, esters, and amides of these compounds, were found to have herbicidal utility.

Herbicidal 2-(phenoxy or phenylthio)-2-(,3,5-triazinyloxy) alkanoic acids

Dibenzo[d,g][1,3]dioxocin-6-carboxylic acids substituted by methyl or ethyl or a moiety --CH.sub.2 CH.sub.2 -- at the 12-position and optionally substituted at other positions, such as methyl 4'-chlorospiro(cyclopropane-1,12'(12'H)-dibenzo[d,g][1,3]dioxocin)-6'-carb oxylic acid, and their agriculturally acceptable esters, amides, and salts are useful for the control of undesirable vegetation. The 1,1-diarylcyclopropane intermediates required for the spirocyclopropane compounds can be prepared from appropriately substituted 1,1-diarylethene procursors by reaction with phenylthiomethyl lithium reagent.

Herbicidal 12-substituted 12H-dibenzo[d,g]dioxocin-6-carboxylic acids

2-(Phenoxy or phenylthio)-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoic acid compounds, such as ethyl 2-(2-fluorophenoxy)-2-(4,6-dimethylpyrimidin-2-yl-oxy)acetate, were prepared by the reaction of a phenol or thiophenol compound with a 2-chloro-2-(pyrimidinyloxy or 1,3,5-triazinyloxy)alkanoate ester compound or by the reaction of a pyrimidinol or 1,3,5-triazinol with a 2-bromo-2-(phenoxy or phenylthio)alkanoate ester. These compounds, and, especially, agriculturally acceptable salts, esters, and amides of these compounds, were found to have herbicidal utility.

Herbicidal 2-(phenoxy or phenylthio)-2-(pyrimidinyloxy or

Herbicidal 12-substituted 12H-dibenzo[d,g][1,3]dioxocin-6-carboxylic

A method of preparing a compound of Formula XII ##STR1## wherein R.sub.1 and R.sub.2 together represent the fragment --Ch.sub.2 CH.sub.2 --;

Method of preparing bis-phenol ethers

12H-Dibenzo[d,g][1,3]dioxocin-6-carboxylic acids having at least one selected substituent in the 1-, 3-, 4-, 8-, 9-, or 11-position, such as 4-chloro-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylic acid, and their agriculturally acceptable salts, esters, and amides, are useful for the control of undesirable vegetation.

Herbicidal 12H-dibenzo[d,g][1,3]dioxocin-6-carboxylic acids

Herbicidal 12-substituted 12H-dibenzo(D,G)(1,3)dioxocin-6-carboxylic

Alkyl esters of 2-fluoro-1-methoxyethylcarbamic acid, which are useful intermediates in the preparation of compounds, such as 4-amino-5-fluoropentanoic acid, are prepared by the electrochemical anodic oxidation of esters of 2-fluoroethylcarbamic acid in the presence of methanol and an electrolyte.

Alkyl 2-fluoro-1-methoxyethylcarbamates

Alkyl esters of 2-fluoro-1-methoxyethylcarbamic acid, which are useful intermediates in the preparation of compounds, such as 4-amino-5- fluoropentanoic acid, are prepared by the electrochemical anodic oxidation of esters of 2-fluoroethylcarbamic acid in the presence of methanol and an electrolyte.

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Walnut Creek, CA, United States of America

Michael G Smith