Metofluthrin: A Potent New Synthetic Pyrethroid with High Vapor Activity against Mosquitoes

Ujihara, Kazuya; Mori, T.; Iwasaki, Takashi; Sugano, Masayo; Shono, Yoshinori; Matsuo, Nobutake

doi:10.1271/bbb.68.170

Cited by 68 publications

(40 citation statements)

References 5 publications

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“…[8][9][10] Furthermore, burning mosquito coils release significant amounts of fine particulate matter and volatile organic compounds that may pose an acute and chronic risk to human health. 11 However, studies into the insecticidal activity of norchrysanthemic acid esters with high vapor activity at ambient temperature by Ujiahra and others 12 identified a synthetic pyrethroid insecticide ("metofluthrin") that doesn't require a heating source and was extremely effective at knocking down Culex pipiens pallens in the laboratory. Metofluthrin has also been shown, with aspirator collections, to provide spatial repellency to mosquitoes in outdoor shelters without walls 13,14 and in houses.…”

Section: Introductionmentioning

confidence: 99%

The Effects of Sustained Release Metofluthrin on the Biting, Movement, and Mortality of Aedes aegypti in a Domestic Setting

Rapley¹,

Russell²,

Montgomery³

et al. 2009

The American Journal of Tropical Medicine and Hygiene

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Abstract. The impact of a sustained release metofluthrin emanator and an allethrin-based mosquito coil on biting, movement and mortality of female Aedes aegypti was assessed in an apartment. In the room in which the metofluthrin emanator was activated, mosquito biting counts were reduced to zero. Metofluthrin also had a spillover effect, significantly ( P < 0.001) reducing biting counts in a neighboring room 1, 4, and 24 hours after the emanator was activated when compared with either the coil or control (untreated) treatment. Mosquitoes were neither repelled nor expelled from a room exposed to metofluthrin. Indeed, a significantly ( P = 0.023) greater proportion of mosquitoes were found in the treated room after exposure to metofluthrin when compared with either the coil or control treatment. Furthermore, in the room treated with metofluthrin the majority of mosquitoes died and a spillover effect into the neighboring room caused greater than one-third mortality of the mosquitoes. Metofluthrin could be used to prevent dengue transmission within a household.

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Section: Introductionmentioning

confidence: 99%

The Effects of Sustained Release Metofluthrin on the Biting, Movement, and Mortality of Aedes aegypti in a Domestic Setting

Rapley¹,

Russell²,

Montgomery³

et al. 2009

The American Journal of Tropical Medicine and Hygiene

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“…11,[15][16][17] The chemical purity of each metabolite was determined by HPLC to be greater than 98%. VII (99.4%) and IX (>97%) were purchased from Showa Denko K.K.…”

Section: Chemicalsmentioning

confidence: 99%

“…10) Metofluthrin (I) (SumiOne ® , Eminence ® ) [2,3,5,6-tetrafluoro-4-(methoxymethyl) benzyl(1R,3R)-2,2-dimethyl-3-((1EZ)-prop-1-enyl) cyclopropanecarboxylate] is a new pyrethroid insecticide with an extremely high knockdown activity, especially against mosquitoes. 11,12) Similarly to other pyrethroids, I exhibits high acute toxicity to common carp (Cyprinus carpio) and rainbow trout (Oncorhynchus mykiss) with 96-hr LC 50 of 0.0012 and 0.00306 mg/L, respectively, and to Daphnia magna with 48-hr EC 50 of 0.0047 mg/L, while it is much less toxic to green algae (Pseudokirchneriella subcapitata) with 72-hr E b C 50 of 0.16 mg/L. [12][13][14] Considering the typical use pattern of I, which is distributed into the air by vaporization as a mosquito adulticide, its direct emission into the aquatic environment is most unlikely.…”

Section: Introductionmentioning

confidence: 99%

Acute aquatic toxicity of metofluthrin metabolites in the environment

et al. 2013

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Acute aquatic toxicity of eight major metabolites of the pyrethroid insecticide metofluthrin, potentially formed via oxidation and ester cleavage in the environment, was examined using three representative species, fathead minnow (Pimephales promelas), Daphnia magna and green alga (Pseudokirchneriella subcapitata). All metabolites showed a wide range of toxicity but were more than a hundredfold and tenfold less toxic than metofluthrin to pyrethroid-sensitive (fish and daphnid) and -insensitive (algal) taxa, respectively; 0.44 to >120 mg/L (fish 96-hr LC 50 ), 6.3 to >120 mg/L(daphnid 48-hr EC 50 ), and 2.6 to >110 mg/L (algal 96-hr E y C 50 ). The structural modification via ester cleavage and/or oxidation was found to significantly control the acute aquatic toxicity of the metabolites. The decreased lipophilicity in the metabolites generally resulted in much less acute toxicity, the extent of which was dependent on an introduced functional group such as formyl as a toxicophore and carboxyl causing a higher acidity.

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“…The non-radiolabeled isomers of I, the corresponding acids (RTZ-II and RTE-II) and alcohol (III) together with the oxidized esters (IV and V) were synthesized in our laboratory according to the reported methods. 1 (CϭO). The chemical purity of each standard was determined to be Ͼ95% by high-performance liquid chromatography (HPLC).…”

Section: Chemicalsmentioning

confidence: 99%

“…Metofluthrin (I) [SumiOne ® , Eminence ® , 2,3,5,6-tetrafluoro-4-(methoxymethyl)-benzyl (EZ)-(1R,3R)-2,2-dimethyl-3-(prop-1-enyl)cyclopropanecarboxylate] is a new pyrethroid insecticide for public hygiene developed by Sumitomo Chemical Co., Ltd. 1,2) The eight isomers are possible for I due to the presence of two optically active centers and geometrical isomerization in its acid moiety. The active insecticide ingredient consists of 1R-trans isomers having the E/Z geometrical composition of 1/8, 2) abbreviated as RTE-I and RTZ-I.…”

Section: Introductionmentioning

confidence: 99%

Hydrolysis and photolysis of insecticide metofluthrin in water

2010

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Metofluthrin [I, 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (EZ)-(1R,3R)-2,2-dimethyl-3-(prop-1-enyl)cyclopropanecarboxylate] was resistant to hydrolysis at pH 4 and 7 but moderately hydrolyzed with a half-life of 36.8 days at pH 9 and 25 o C to form the corresponding acid and alcohol via ester cleavage. The activation energy was estimated to be 105 kJ mol Ϫ1 based on the hydrolysis rates at 25-50 o C. By continuous exposure to light at Ͼ290 nm from a Xenon arc lamp at hydrolytically stable pH 4 and 25 o C, I was rapidly photodegraded with half-lives of 1.1-3.4 days, mainly via ester cleavage and successive oxidation followed by mineralization to carbon dioxide. Spectroscopic analyses together with co-chromatography with authentic standards showed that the major degradates having an ester linkage were the aldehyde and carboxylic acid derivatives formed via oxidative cleavage of the prop-1-enyl group together with the diol formed possibly through an oxidative intermediate, such as an epoxide.

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Metofluthrin: A Potent New Synthetic Pyrethroid with High Vapor Activity against Mosquitoes

Cited by 68 publications

References 5 publications

The Effects of Sustained Release Metofluthrin on the Biting, Movement, and Mortality of Aedes aegypti in a Domestic Setting

The Effects of Sustained Release Metofluthrin on the Biting, Movement, and Mortality of Aedes aegypti in a Domestic Setting

Acute aquatic toxicity of metofluthrin metabolites in the environment

Hydrolysis and photolysis of insecticide metofluthrin in water

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