Synthesis and Evaluation of Heterocyclic Analogues of Bromoxynil was written by Cutulle, Matthew A.;Armel, Gregory R.;Brosnan, James T.;Best, Michael D.;Kopsell, Dean A.;Bruce, Barry D.;Bostic, Heidi E.;Layton, Donovan S.. And the article was included in Journal of Agricultural and Food Chemistry in 2014.Recommanded Product: 2,6-Dibromoisonicotinonitrile This article mentions the following:
One attractive strategy to discover more active and/or crop-selective herbicides is to make structural changes to currently registered compounds This strategy is especially appealing for those compounds with limited herbicide resistance and whose chem. is accompanied with transgenic tools to enable herbicide tolerance in crop plants. Bromoxynil (I) is a photosystem II (PSII) inhibitor registered for control of broadleaf weeds in several agronomic and specialty crops. Recently at the University of Tennessee-Knoxville several analogs of bromoxynil were synthesized including a previously synthesized pyridine (2,6-dibromo-5-hydroxypyridine-2-carbonitrile sodium salt), a novel pyrimidine (4,6-dibromo-5-hydroxypyrimidine-2-carbonitrile sodium salt), and a novel pyridine N-oxide (2,6-dibromo-1-oxidopyridin-1-ium-4-carbonitrile). These new analogs of bromoxynil were also evaluated for their herbicidal activity on soybean (Glycine max), cotton (Gossypium hirsutum), redroot pigweed (Amaranthus retroflexus), velvetleaf (Abutilon theophrasti), large crabgrass (Digitaria sanguinalis), and pitted morning glory (Ipomoea lacunose) when applied at 0.28 kg ha-1. A second study was conducted on a glyphosate-resistant weed (Amaranthus palmeri) with the compounds being applied at 0.56 kg ha-1. Although all compounds were believed to inhibit PSII by binding in the quinone binding pocket of D1, the pyridine and pyridine-N-oxide analogs were clearly more potent than bromoxynil on Amaranthus retroflexus. However, application of the pyrimidine herbicide resulted in the least injury to all species tested. These variations in efficacy were investigated using mol. docking simulations, which indicate that the pyridine analog may form a stronger hydrogen bond in the pocket of the D1 protein than the original bromoxynil. A pyridine analog was able to control the glyphosate-resistant Amaranthus palmeri with >80% efficacy. The pyridine analogs of bromoxynil showed potential to have a different weed control spectrum compared to bromoxynil. A pyridine analog of bromoxynil synthesized in this research controlled several weed species greater than bromoxynil itself, potentially due to enhanced binding within the PSII binding pocket. Future research should compare this analog to bromoxynil using optimized formulations at higher application rates. In the experiment, the researchers used many compounds, for example, 2,6-Dibromoisonicotinonitrile (cas: 408352-58-9Recommanded Product: 2,6-Dibromoisonicotinonitrile).
2,6-Dibromoisonicotinonitrile (cas: 408352-58-9) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Recommanded Product: 2,6-Dibromoisonicotinonitrile