Metofluthrin

For transfluthrin (30) and metofluthrin (31), volatilization at room temperature is hardly expected, requiring wind, centrifugal force, and other effects. Nevertheless, with a slight move of air, these compounds possibly have the effect of preventing insects from coming into a house to some extent because they are effective in minimal amounts against mosquitoes, with dozens of times higher potency than allethrin. 

Ujihara K, Mori T, Iwasaki T, Sugano M, Shono Y, Matsuo N (2004) Metofluthrin a potent new synthetic pyrethroid with high vapor activity against mosquitoes. Biosci Biotechnol Biochem 68(1) 170-174... 

Table 2 Efficiency of metofluthrin in a non-heating vapor formulation with a fan and mosquito coil formulations aganinst various mosquito species ...

Formulation Species Cone. (%) KT50 (min) Metofluthrin d-Allethrin... 

Metofluthrin has high knockdown activity against mosquitoes and has an excellent mammalian safety profile. Metofluthrin is suitable for use not only in various... 

The acid moiety of metofluthrin is (T/ )-norchrysanthemic acid. In this section we describe the development of synthetic studies of Z-rich norchrysanthemic acid. Aforementioned norchrysanthemic acid was first synthesized by Staudinger in 1924 as the pyrolytic decomposition product of chrysanthemun dicarboxylic... 

There are two asymmetric carbon atoms and E, Z-isomers in norchrysanthemic acid. So, there exist eight stereoisomers. In order to elucidate the structure activity relationship of metofluthrin stereoisomers, we investigated the synthetic pathways of all stereoisomers of norchrysanthemic acid. 

In conclusion, all of the eight stereoisomers of norchrysanthemic acid methyl esters were synthesized in stereoselective manner starting from (1/ )-inmv-chrysanthemic acid or (+)-3-carene. All stereoisomers of metofluthrin were synthesized in our laboratory. Their structure-activity relationship will be published elsewhere. 

Metofluthrin (I) The committee determined that the new data were sufficient to support a mitogenic mode of action for the development of liver tumors in rats exposed to metofluthrin in the carcinogenicity study. The report summarized mode of action study data that characterized effects such as increased P450 enzyme levels, increased smooth endoplasmic reticulum, hepatocellular hypertrophy, hepatocellular proliferation, and inhibition of intracellular communication, which were described as steps leading to tumor development via a nongenotoxic mechanism (i.e., mitogenicity). Some of these studies used sodium phenobarbital as a positive control,... 

Case Study 1 An evaluation of the human relevance of the synthetic pyrethroid metofluthrin-induced liver tumors in rats based on mode of action [115-117]... 

Based on the in vitro results and the rat in vivo studies at different exposure levels, induction of CYP isoforms in human hepatocytes is considerably lower for metofluthrin than phenobarbital at identical concentrations [115, 116]. 

Matsuo N, Ujihara K, Shono Y et al (2005) Dicovery and development of a novel pyrethroid insecticide Metofluthrin (SumiOne, Eminence) . Sumitomo Chemical 2005-11 4-16... 

New York State Department of Environmental Conservation (2008) http //pmep.cce.comell. edu/profiles/insect-mite/fenitrothion-methylpara/metofluthrin/metoflu reg 0608.pdf. Accessed 15 Feb 2011... 

Deguchi Y, Yamada T, Hirose Y et al (2009) Mode of action analysis for the synthetic pyrethroid metofluthrin-induced rat liver tumors evidence for hepatic CYP2B induction and hepatocyte proliferation. Toxicol Sci 108 69-80... 

Hirose Y, Nagahori H, Yamada T et al (2009) Comparison of the effects of the synthetic pyrethroid metofluthrin and phenobarbital on CYP2B form induction and replicative DNA synthesis in cultured rat and human hepatocytes. Toxicology 258 64—69... 

In addition to ozonization, aqueous photolysis of metofluthrin (14) gave the diol derivative possibly formed through epoxidation of the prop-l-enyl side chain in the acid moiety followed by its hydrolysis [56]. 

Nishiyama M, Suzuki Y, Katagi T (2010) Hydrolysis and photolysis of insecticide metofluthrin in water. J Pestic Sci 35 447 155... 

Kodaka R, Suzuki Y, Sugano T, Katagi T (2007) Aerobic metabolism and adsorption of pyrethroid insecticide metofluthrin in soil. J Pestic Sci 32 393-401... 

Abstract Metofluthrin (commercial name SumiOne, Eminence ) is a novel pyrethroid insecticide developed by Sumitomo Chemical Co., Ltd. Metofluthrin has extremely high insecticidal activity to various pest insects, especially to mosquitoes. In addition, Metofluthrin has relatively high volatility and low mammalian toxicity. Metofluthrin is therefore suitable for use not only in conventional mosquito control formulations such as coils and liquid vaporizers, but also in a variety of novel devices that do not require heating, such as fan vaporizers and paper and resin emanators. Here we describe the insecticidal activity of Metofluthrin mainly against mosquitoes in various formulations in both laboratory and field trials. 

Keywords Biting inhibition Field Insecticidal activity Metofluthrin Mosquito... 

Basic Insecticidal Activity of Metofluthrin in Laboratory Studies. 205... 

Metofluthrin (SumiOne 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (EZ(E/ Z = 1/8))-(lR, 3/ )-2,2-dimethyl-3-(prop-l-enyl)cyclopropanecarboxylate, Fig. 1) is a novel pyrethroid insecticide discovered by Sumitomo Chemical Co., Ltd. [1], Metofluthrin was registered in more than 20 countries including Japan and USA and is currently under worldwide development for a variety of environmental health applications. 

Metofluthrin is a suitable active ingredient for various formulations and devices due to its high lethal/knockdown activity against pest insects (especially mosquitoes), as well as having low mammalian toxicity and favorable physicochemical properties. This report summarizes its outstanding efficacy in various mosquito control formulations in both laboratory tests and field trials [2],... 

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