Heretofore some kinds of 4-aryl-4-halopyrazolidine-3,5-dione derivatives have been known. For example, An. Quim. vol. 71, 396 to 399 (1975) discloses that compounds A, B and C to be described later, i.e. 4-aryl-4-halopyrazolidine-3,5-dione derivatives, can be prepared by Diels-Alder reaction between 4-chloro-4-phenylpyrazoline-3,5-dione and diene. Further An. Quim. vol. 75, 931 to 935 (1979) describes the under-mentioned compounds D and E as an intermediate for preparing 13,14-azasteroid, the compounds being prepared by Diels-Alder reaction between 4-chloro-4-phenylpyrazoline-3,5-dione and diene. In addition, Comment., Pontif. Acad. Sci. vol.2, 8 (1975) sets forth that compounds A, B and C to be described later can be prepared by chlorination of the corresponding 4-phenylpyrazolidine-3,5-dione derivative.
However, the compounds of the invention represented by the formula (1) are novel compounds which are not included in conventional compounds.
On the other hand, 4-aryl-4-nitropyrazolidine-3,5-dione derivatives are entirely novel compounds. ##STR2##
With insecticides and miticides in use for many years, pest insects have acquired resistance in recent years and become difficult to control with conventional insecticides. Accordingly it is expected to develop novel insecticides. Also in the herbicide field, the development of novel herbicides are expected.
An object of the present invention is to provide 4-aryl-4-substituted pyrazolidine-3,5-dione derivatives which have not only extremely high insecticidal and miticidal activities but a high herbicidal activity.