Takaaki Miyake

Synthesis and Insecticidal Activity of Novel N-Oxydihydropyrrole Derivatives with a Substituted Spirocyclohexyl Group

A series of 5-spirocyclohexyl-3-(2,6-dimethylphenyl)-1,5-dihydro-2H-pyrrol-2-one derivatives (3) with various substituents on the spirocyclohexyl ring was synthesized and evaluated for its insecticidal activity against the aphid, Myzus persicae. Substituents at the 1- and 4-positions of the dihydropyrrole ring were also varied to optimize the activity. An investigation of the structure-activity relationship revealed that methoxy, alkoxyalkoxy, ethylenedioxy and methoxyimino groups were favorable as substituents at the 4-position of the spirocyclohexyl ring. The activity was optimized by the respective substitution of a methoxy or methoxymethoxy moiety and cyclopropylcarbonyloxy group at the 1- and 4-positions of the dihydropyrrole ring.

Synthesis and insecticidal activity of novel N-oxydihydropyrroles: 4-hydroxy-3-mesityl-1-methoxymethoxy derivatives with various substituents at the 5-position.

This paper reports the synthesis and insecticidal activity of a series of novel 4-hydroxy-3-mesityl-1-methoxymethoxy-1,5-dihydro-2H-pyrrol-2-one derivatives, in which the substituents at the 5-position were varied with a number of alkyl and spirocycloalkyl groups. Investigation of the structure-activity relationships revealed that small alkyl and spirocyclohexyl groups had a favorable effect on the insecticidal activity of these agents against Myzus persicae.

Synthesis and insecticidal activity of novel dihydropyrrole derivatives with N-sulfanyl, sulfinyl, and sulfonyl moieties.

This paper reports the synthesis and insecticidal activity of a new type of dihydropyrrole derivatives with sulfur moieties such as sulfanyl, sulfinyl, and sulfonyl groups at the 1-position. These derivatives exhibited high insecticidal potency against Nilaparvata lugens and Nephotettix cincticeps. Investigation of the structure-activity relationships revealed that the alkoxycarbonyloxy groups at the 4-position tended to increase the systemic insecticidal activity.

Synthesis and Insecticidal Activity of N-Oxydihydropyrroles: 4-Hydroxy-3-mesityl-5,5-dimethyl Derivatives with Various Substituents at the 1-Position

A new series of N-oxydihydropyrrole derivatives was synthesized and evaluated for insecticidal activity against Nilaparvata lugens and Myzus persicae. Various substituents were introduced to the 1-position of the dihydropyrrole ring, and the derivatives obtained exhibited systemic and/or contact insecticidal activity. The structure-activity relationship revealed that small alkyoxy and alkoxyalkoxy groups were more favorable than alkylcarbonyloxy, alkoxycarbonyloxy, or sulfonyloxy groups as substituents at the 1-position.