Substituted cyclopropanecarboxylic acid esters and pesticidal compositions containing the same as active ingredient

DETAILED DESCRIPTION OF THE INVENTION The present invention is directed to new pyrethroid compounds which are substituted cyclopropanecarboxylic acid esters of the general formula: ##STR10## wherein A is a hydrogen atom or an ethynyl group.
The subject compounds possess potent, broad spectrum pesticidal activity and are low in toxicity to man, and domestic animals and particularly low in toxicity in fish.
The pesticidal activity of the compounds according to this invention against green rice leafhoppers (Nephotettix cincticeps Uhler), rice stem borers (Chilo suppressalis Walker), tobacco cutworms (Prodenia litura Koch) and houseflies (Musca domestica), as examples of the pests against which the same compounds are considered effective, the acute toxicity data on the same compounds as determined in rat by the oral route and the median tolerance limit (TLm) data on the same compounds as determined in killifish (Orizias latipes) and guppies (Lebistes reticulatus) are shown in Table 1 alongside the corresponding values for various control compounds.
The pesticidal effects were determined by the procedures set forth in Test Examples 1 through 4, while the acute toxicity to rat was determined by the procedure set forth in Test Example 9 and the toxicity to fish was determined by the procedures set forth in Test Examples 6 and 7, all those Examples appearing hereinafter.
As will be apparent from Table 1, Test Examples 5 and 8, and Utility Examples 1 and 5 which appear hereinafter, Compounds (1) and (2) according to this invention are at least equivalent or superior in pesticidal effectiveness to control compounds (A), (B), (C), (D), (E), (F), (G) and (H) and, yet, are lower in toxicity to fish than the same control compounds, the toxicity values for our compounds being only one-fifth (1/5) to one-three thousandth (1/3000).
In view of higher pesticidal activity and excellent low toxicity, the Compounds (1) and (2) each consisting principally or essentially of the trans-isomer in relation to the three-membered ring structure are particularly preferable