Synergism by Propynyl Aryl Ethers in Permethrin-Resistant Tobacco Budworm Larvae,<i>Heliothis virescens</i>

Brown, Thomas M.; Bryson, Patricia K.; Payne, Gregory T.

doi:10.1002/(sici)1096-9063(199604)46:4<323::aid-ps376>3.0.co;2-y

Cited by 37 publications

(25 citation statements)

References 25 publications

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“…The involvement of oxidases and esterases in permethrin resistance were investigated by using their inhibitors as synergists. Another P450 monooxygenase inhibitor, PTPE (Casida, 1970;Brown et al, 1996), also decreased the resistance level from 2,500-fold to fifteen fold when larvae were treated at the maximum sublethal concentration (i.e., 4 µg/ml for the JPal-per and 1 µg/ml for the susceptible strain). The PBO showed a significant effect on permethrin toxicity in both strains (Table 1).…”

Section: Results Bioassaymentioning

confidence: 98%

P450 monooxygenases are an important mechanism of permethrin resistance in Culex quinquefasciatus Say larvae

Kasai

Weerashinghe

Shono

1998

Arch. Insect Biochem. Physiol.

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Culex quinquefasciatus Say from Saudi Arabia (JPal-per) showed high levels of resistance (2,500-fold) to permethrin. A major contribution of cytochrome P450 monooxygenases as a mechanism of resistance was suggested by the large synergistic effects of oxidase inhibitors such as 2-propynyl 2,3,6-trichlorophenyl ether (PTPE) and piperonyl butoxide (PBO) on the toxicity of permethrin in the resistant strain. Contents of cytochrome P450 and b 5 were about 2.5 times higher in the JPal-per strain than those in the susceptible strain. P450 monooxygenase in the microsomes of gut and other parts of the body metabolized permethrin to 4´-HO-permethrin and other metabolites. Degradation of permethrin by microsomal P450 enzymes was much greater in the resistant JPal-per strain and was inhibited by PBO and PTPE. In addition to a kdr type mechanism which seems to work in the larvae, cytochrome P450 monooxygenase is clearly shown to play an important role as a mechanism of permethrin resistance in JPal-per strain larvae. Arch. Insect Biochem. Physiol. 37:47-56, 1998. © 1998 Wiley-Liss, Inc.Key words: resistance; pyrethroid; permethrin; mosquito; Culex quinquefasciatus; metabolismAbbreviations used: DEF = S-S-S-tributylphosphorotrithioate; DMC = 1,1-bis (p-chlorophenyl) ethanol; DTT = threo-1,4-dimercapto-2,3-butanediol; p-APMSF = p-amidinophenyl-methanesulfonyl fluoride hydrochloride; PB acid = 3-phenoxy-benzyl acid; PB alc. = 3-phenoxy-benzyl alcohol; PBO = piperonyl butoxide; PTPE = 2-propynyl 2,3,6-trichlorophenyl ether; PTU = 1-phenyl-2-thiourea.

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Section: Results Bioassaymentioning

confidence: 98%

P450 monooxygenases are an important mechanism of permethrin resistance in Culex quinquefasciatus Say larvae

Kasai

Weerashinghe

Shono

1998

Arch. Insect Biochem. Physiol.

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“…They attributed antagonism to possible interference by one component with enzymes responsible for activation of the other; they based this explanation primarily upon the work of DuBois (1961) with various organophosphates. Metabolism of pyrethroids is catalyzed by pyrethroid-hydrolyzing esterases (i.e., carboxylesterases/B-esterases) (Gunning et al 1999) and cytochrome P450 monooxygenases (Brown and Bryson 1996). Metabolism of chlorantraniliprole in mammals is catalyzed by cytochrome P450s and hydroxylases (PMRA 2008, U.S. EPA 2008.…”

Section: Resultsmentioning

confidence: 99%

Toxicity of Thiamethoxam and Mixtures of Chlorantraniliprole Plus Acetamiprid, Esfenvalerate, or Thiamethoxam to Neonates of Oriental Fruit Moth (Lepidoptera: Tortricidae)

Jones¹,

Robertson²,

Weinzierl³

2012

jnl. econ. entom.

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To assess the toxicity ofthiamethoxam and three mixtures of insecticides to oriental fruit moth, Grapholita molesta (Busck) (Lepidoptera: Tortricidae), we added the insecticides to diet and fed it to neonates of two laboratory colonies; mortality was assessed after 96 h. Thiamethoxam was much less toxic than insecticides previously tested. Five of six analyses of the joint action of chlorantraniliprole plus acetamiprid, esfenvalerate, or thiamethoxam indicated that toxicity was not independent and not correlated. For chlorantraniliprole plus acetamiprid, mortality was slightly lower than expected at low concentrations and greater than expected at high concentrations. For chlorantraniliprole plus esfenvalerate, mortality was less than expected at nearly all concentrations, suggesting antagonism despite the two compounds' different modes of action. For chlorantraniliprole plus thiamethoxam, observed mortality exceeded expected mortality at low concentrations, but this trend did not continue at higher concentrations. Although the null hypothesis of independent and uncorrelated toxicity was rejected for chlorantraniliprole plus acetamiprid and chlorantraniliprole plus thiamethoxam in three of four analyses, differences between observed and expected mortality were minor and inconsistent over the range of concentrations tested. We do not expect these mixtures to exhibit significant synergism or antagonism in the field. Apparent antagonism between chlorantraniliprole and esfenvalerate is particularly relevant because these insecticides (or chlorantraniliprole plus a different pyrethroid) may be used together in apples or peaches for control of oriental fruit moth and hemipteran pests. The effectiveness of each insecticide against oriental fruit moth might be reduced in such applications.

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“…These alkynyl ethers block metabolic detoxification mediated by cytochrome P450 monooxygenases and thus are used as research tools to evaluate the possible mechanism of the biological breakdown of pesticides 5. 6 Despite their potential in the field of resistance management,7, 8 it is intriguing that no successful product of this type is currently used in crop protection 9. The main problem, in addition to manufacturing costs and questions of biological safety of metabolism inhibitors, is the extent and cost of development work to produce the data needed for registration of two‐component mixtures.…”

Section: Introductionmentioning

confidence: 99%

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

Bertók¹,

Pap²,

Árvai³

et al. 2003

Pest Management Science

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Structure-activity relationships of aryl alkynyl synergists of the general formula of Ar-Q-R, where Q represents a bridging structure, were studied using a standardised testing system and Relative Potency values. Ethers, esters, oxime ethers, amides and amines were prepared and evaluated. The length of the R-alkynyl chain, the role of the bridge and the substitution of the aromatic ring were examined systematically. The most potent compounds possessed an aromatic ring connected via a bridge of three atoms to an alkynyl chain, forming together a linear side-chain of six atoms. Several highly potent compounds were synthesised of which one (MB-599; proposed common name verbutin) was selected for development as a selective insecticide synergist in crop protection. Its high potential at practical insecticide:synergist ratios makes possible the reduction of the total amount of insect-control chemicals applied, and its use as an additive to produce new formulations of existing insecticides makes it highly advantageous in resistance management, giving a new tool to sustain the effectiveness of a wide range of insecticides. A product containing a (1+1) mixture of verbutin and beta-cypermethrin was launched in Hungary in 2002.

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Synergism by Propynyl Aryl Ethers in Permethrin-Resistant Tobacco Budworm Larvae,Heliothis virescens

Cited by 37 publications

References 25 publications

P450 monooxygenases are an important mechanism of permethrin resistance in Culex quinquefasciatus Say larvae

P450 monooxygenases are an important mechanism of permethrin resistance in Culex quinquefasciatus Say larvae

Toxicity of Thiamethoxam and Mixtures of Chlorantraniliprole Plus Acetamiprid, Esfenvalerate, or Thiamethoxam to Neonates of Oriental Fruit Moth (Lepidoptera: Tortricidae)

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

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