Aryloxy- and Pyridyloxyphenylcyclohexanedione Grass Herbicides

Monoclonal-Based ELISA for the Identification of Herbicidal Cyclohexanedione Analogues That Inhibit Graminaceous Acetyl Coenzyme-A Carboxylase

“…Monoclonal antibodies mAb A and mAb B were able to segregate most of the inactive cyclohexanedione analogues on the basis of their IC 50 values because these analogues lack critical functional groups associated with the cyclohexanedione pharmacophore (Markley et al, 1995;Webb et al, 1997). For instance, the cyclohexane ring is absent in analogues 20 and 24 (Figure 2).…”

“…Furthermore, analogue 20 has a phenyl substituent at position 6 of the six-member ring, which is not present on analogue A (Figure 1), the hapten used to construct the immunogen. Inactive analogues 7, 18, and 21 (Figure 2) are missing the critical oxime functional group at position 2 of cyclohexane ring (Markley et al, 1995;Webb et al, 1997). However, analogue 22 (Figure 2) possesses all of the critical functional groups associated with active cyclohexanedione inhibitors, namely, a cyclohexane ring with a carbonyl group at position 1, an oxyimino group at position 2, and a hydroxyl group at position 3 (Markley et al, 1995;Webb et al, 1997).…”

“…Inactive analogues 7, 18, and 21 (Figure 2) are missing the critical oxime functional group at position 2 of cyclohexane ring (Markley et al, 1995;Webb et al, 1997). However, analogue 22 (Figure 2) possesses all of the critical functional groups associated with active cyclohexanedione inhibitors, namely, a cyclohexane ring with a carbonyl group at position 1, an oxyimino group at position 2, and a hydroxyl group at position 3 (Markley et al, 1995;Webb et al, 1997). The lack of ACCase inhibition by analogue 22 is attributed to the presence of the large ortho substituent on the phenyl group at position 5 of the cyclohexane ring (Figure 2).…”

“…The lack of ACCase inhibition by analogue 22 is attributed to the presence of the large ortho substituent on the phenyl group at position 5 of the cyclohexane ring (Figure 2). The large ortho substituent may prevent physical interaction between analogue 22 and the putative cyclohexanedione-inhibitor binding site on ACCase (Cseke, personal communication, 1993;Markley et al, 1995). Analogue 22 cross-reacts with both mAb A and mAb B because the critical pharmacophore functional groups on the cyclohexane ring and oxyimino substituents are identical to analogue A (Figure 1).…”

Interaction of Cyclohexanediones with Acetyl Coenzyme-A Carboxylase and an Artificial Target-Site Antibody Mimic: A Comparative Molecular Field Analysis

“…The generic cyclohexanedione-inhibitor structure is illustrated in Figure 3. The core structural features common to all active cyclohexanedione inhibitors are carbonyl, oxyimino, and hydroxyl functional groups at positions 1, 2, and 3 of the cyclohexane ring, respectively (Figure 3; Markley et al, 1995;Webb et al, 1997). The nature and type of substituents at R 1 , R 2 , R 3 , and R 4 are variable when compared to the core structure, and the precise role these substituents play in binding to ACCase is not known (Markley et al, 1995;Webb et al, 1997).…”