9223. Tetramethrin

Nomenclature

CAS number: 7696-12-0
2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid (1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)methyl ester; 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid ester with N-(hydroxymethyl)-1-cyclohexene-1,2-dicarboximide; N-(3,4,5,6-tetrahydrophthalimide)methyl-cis,trans-chrysanthemate; N-(chrysanthemoxymethyl)-1-cyclohexene-1,2-dicarboximide; phthalthrin; FMC-9260; SP-1103; Neo-Pynamin (Sumitomo).
C19H25NO4; mol wt 331.41.
C 68.86%, H 7.60%, N 4.23%, O 19.31%.

Description and references

Synthetic pyrethroid insecticide. Prepn of racemic mixture: T. Kato et al., JP 65 8535; eidem, US 3268398 (1965, 1966 both to Sumitomo). Activity: eidem, Agric. Biol. Chem. 28, 914 (1965). Comparative activity of isomers: Y. Okuno et al., DE 2348930; eidem, US 3934023 (1973, 1976 both to Sumitomo). Metabolism: J. Miyamoto et al., Agric. Biol. Chem. 32, 628 (1968). Photodecompn: Y.-L. Chen, J. E. Casida, J. Agric. Food Chem. 17, 208 (1969). Toxicity study: T. Kato et al., Agric. Biol. Chem. 28, 914 (1965). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.

Chemical structure

Properties

The commercial product is a mixture of isomers. White crystalline solid, mp 65-80°. d2020 1.108; nD21.5 1.5175. LD50 orally in mice: 1000 mg/kg (Kato).

Use

Insecticide.