Herbicidal activity of heterocyclic dichlobenil analogues

Abstract

Heterocyclic changes in the chemical structure of existing herbicides may provide new options for weed management. Pyridine and pyrimidine analogues of dichlobenil were evaluated for weed control in ornamental production. All compounds were preemergently applied at 1, 5, and 10 kg/ha to large crabgrass (Digitaria sanguinalis), common purslane (Portulaca oleracea), and Japanese holly (Ilex crenata). The pyrimidine analogue, 4,6-dichloropyrimidine-5-carbonitrile, controlled large crabgrass and common purslane similar to the active ingredient in dichlobenil at 10 kg/ha.

An Alternative Scalable Process for the Synthesis of 4,6-Dichloropyrimidine-5-carbonitrile

“…All commercially available reagents and solvents were used directly as received. 1 H NMR spectra were recorded on Varian 400 and 500 MHz spectrometers. Chemical shifts (δ) are reported in parts per million and coupling constants (J) in hertz.…”

“…4,6-Dichloropyrimidine-5-carbonitrile ( 1 ) is a key intermediate and constitutes one of the most important heterocyclic compositions or subunits in pesticides, − color couplers, and pharmaceutically active compounds. − Despite its usefulness in many drug candidates and molecules for various applications, a truly convenient process for its large-scale production has not been published to date. ,− As part of an ongoing clinical program, a practical synthesis of 1 was required. The extensive use of 4,6-dichloropyrimidine-5-carbonitrile intermediates in pharmaceutically active compounds stimulated the development of a method for their synthesis.…”

“…1 H NMR (400 MHz, DMSO-d 6 ): δ 8.96 (s, 1H). GC−MS: [M] + , 173.■ ASSOCIATED CONTENT* S Supporting InformationThe Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.oprd.8b00154.…”