The Dow Chemical Company

Dowelanco

Patricia G Ray

James M Renga

Michael G Smith

Brian K Riley

Charles Marlowe

William A Kleschick

Robert J Ehr

John C Van Heertum

Mark J Costales

N-(3-, 4-, and 5-)-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide compounds, substituted on the pyrimidine ring with an alkoxy group and on the pyrazine ring, such as N-(4-bromo-1-methylpyrazol-3-yl)-7-chloro-5-methoxy-1,2,4-triazolo[1,5-c]p yrimidine-2-sulfonamide, were prepared from alkoxy substituted 1,2,4-triazolo[1,5-c]-pyrimidine-2-sulfonyl halides by condensation with substituted (3-, 4-, and 5-aminopyrazoles in the presence of a pyridine base and a catalytic amount of dimethyl sulfoxide. The compounds were found to possess general and, in some cases, selective pre- and postemergence herbicidal activity.

N-pyrazolyl-1,2,4-triazolo[1,5-c]pyrimidine-2-sulfonamide herbicides

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

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

Growing community of inventors

Walnut Creek, CA, United States of America

Patricia G Ray