Comparative evaluation of new synergists containing a butynyl-type synergophore group and piperonyl butoxide derivatives

Abstract

Cross-substituted derivatives of piperonyl butoxide (PBO) and MB-599 (proposed common name: verbutin) were synthesized and investigated as carbofuran and permethrin synergists against housefly, Musca domestica L. The majority of PBO and MB-599 derivatives were significantly more potent synergists for carbofuran than for permethrin. PBO, the most important representative of this series was not the most potent synergist for carbofuran or for permethrin. Cleavage of the methylenedioxy ring of methylenedioxyphenyl (MDP) polyether compounds resulted in complete loss of synergistic activity with both insecticides, but it could be restored or even improved by incorporating an alkynyl ether moiety into the molecule. The improved synergistic activity was found to be closely associated with the 2-butynyloxymethyl side-chain, suggesting that this can be regarded as a characteristic synergophore group. MB-599, one of the most promising compounds bearing this group showed considerably higher activity with carbofuran (synergist ratio, SR = 37.8) than with PBO (SR = 6.4). There was no significant difference between synergistic activities of MB-599 (SR = 4.6) and PBO (SR = 4) for permethrin.

Effects of Piperonyl Butoxide and Tetramethrin Combinations on Biological Activities of Selected Synthetic Pyrethroid Insecticides against Different Housefly (Musca domestica L., Diptera: Muscidae) Populations

“…Deltamethrin-PBO synergism was investigated and found to be significant for particular knockdown effect percentage values. These findings showed the importance of PBO for increasing the biological activity of synthetic pyrethroids (Hodgson and Levi 1998;Wickham 1998;Pap et. al.…”

“…This increase in values was determined in almost all populations, and it was found to be significant in some insecticides. These findings are similar to several other studies (Farnham 1998;Stewart 1998;Wickham 1998;Kasai and Scott 2000;Pap et. al.…”

“…It is primarily used as a synergist in space spray, residual, and admixture products for the control of insect pests in or around domestic and commercial premises, especially food preparation areas (Farnham 1998;Wickham 1998;Pap et al 2001). It has a synergistic action with the major classes of insecticides, such as pyrethrins, pyrethroids, carbamates, organophosphates, and many insect growth regulators (Keane 1998;Tomlin 1997).…”

Genetics and evidence for an esterase‐associated mechanism of resistance to indoxacarb in a field population of diamondback moth (Lepidoptera: Plutellidae)

“…The toxicity of indoxacarb was also evaluated in the presence of two potential synergists, piperonyl butoxide (PBO, 980 g L −1 ; Sigma Ltd, UK), an inhibitor of cytochrome P450 monooxygenases (microsomal oxidases) and of esterases, and a PBO analogue, 6‐[2‐(2‐butoxy‐ethoxy)ethoxymethyl]‐5‐propyl‐2,3‐dihydrobenzo[1, 4]dioxin (Endura SpA, Bologna, Italy; provided by G Moores), with a modified methylendioxyphenyl ring, and consequent loss of activity against microsomal oxidases, which is esterase specific 8. Each synergist was applied topically (0.25 µL) at a dose of 10 mg AI mL −1 in acetone solution to the dorsal thoracic segments 1 h prior to exposing the insects to insecticide.…”

Structure–activity relationship study of alkynyl ether insecticide synergists and the development of MB‐599 (verbutin)

“…Acting as metabolism inhibitors, they increase the potency of insecticides, especially of carbamates 2. 3 Although they act on the same target site, their mode of action differs significantly from that of the well‐known methylenedioxyphenyl (MDP) synergists such as piperonyl butoxide (PBO) 4. Their structure can be depicted by the general formula Ar–Q–R (Fig 1) in which the aromatic ring Ar is connected via a bridge Q to an alkynyl (typically propynyl) chain that is responsible for the activity.…”