1-[2-(cyclopropylcarbonyl)-4-fluorophenyl]sulfa moyl)-3-(4,6-dimethoxy-2-pyrimidinyl) urea and its herbicidal method of use

#Weeds cause tremendous global economic losses by reducing crop yields and lowering crop quality. In the United States alone, agronomic crops must compete with hundreds of weed species. In particular, barnyard-grass, broadleaf weeds and sedges cause extensive economic losses.

#U.S. Pat. No. 5,280,007 discloses certain sulfamoyl urea herbicides. However, that patent does not specifically disclose the compound of the present invention.

#It is therefore an object of the present invention to provide a compound which is highly effective for controlling undesirable plant species.

#In order to facilitate a further understanding of the invention, the following examples are presented primarily for the purpose of illustrating more specific details thereof. The invention should not be deemed limited by the examples as the full scope of the invention is defined in the claims. The term NMR designates nuclear magnetic resonance.

#4-Fluoroaniline (5.0 g, 45 mmol), cyclopropyl cyanide (5.0 mL, 68 mmol) and aluminum chloride (6.6 g, 49.5 mmol) are added sequentially to a mixture of boron trichloride (45 mL of a 1.0M solution in methylene chloride) and 1,2-dichloroethane (50 mL) at 0.degree. C. The reaction mixture is warmed to room temperature, distilled until the pot temperature reaches 70.degree. C., refluxed for 18 hours, cooled and diluted with water. The aqueous mixture is extracted with methylene chloride. The organic extracts are combined, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as an orange oil (4.1 g, 51%) which is identified by NMR spectral analysis.

#Using essentially the same procedure, but employing the appropriately substituted aniline, the following compounds are obtained: