Novel insecticidal-miticidal cyclic dithiacarbamoyloximes

Novel insecticidal oxathiolane and oxathiane oxime carbamates

“…In general, the 95% confidence interval for individual LCso's in these tests is LC50/2 to LC50 X 2 (e.g., the Cl for an LC50 of 50 is 25-100). Seemingly subtie changes in the structure of compounds in this oxathia series cause substantial changes in biological activity in a pattern analogous to that observed for the previously reported dithia series (D'Silva et al, 1985). Comparative data for analogous oxathia/dithia pairs given in Table IV indicate that the expectations suggested by the aldicarb and methoxy analogue comparison in Table I were generally realized.…”

“…The previous paper in this series (D'Silva et al, 1985) presents the synthesis and biological properties of a new series of insecticidal oxime carbamate derivatives of 1,3dithiolanes and 1,4-dithianes (la) and gives an overview of earlier important work in insecticidal oxime carbamates. Contemporary with this work on the dithia series, a study was conducted of analogous oxathia compounds generalized by formula lb.…”

Quantitative structure-activity relationships in insecticidal oxathiolane and dithiolane oxime carbamates and related compounds

“…Increasing lipophilicity (log P) uniformly diminishes activity against the arthropods and the rat while the presence of a /3-sulfur as compared to a /3-oxygen is associated with increased activity against all test organisms. These correlation studies suggest that further synthesis in this series is unlikely to yield effective insecticides in which the arthropod/mammal selectivity is improved over that of compounds already in hand.The syntheses and the insecticidal properties of carbamate esters of 4-oximino-l,3-oxathiolanes (la), 3-oximino-l,4-oxathianes (lb;Kurtz et al, 1987), 4-oximino-l,3dithiolanes (Ic), and 3-oximino-l,4-dithianes (Id;D'Silva et al, 1985) have been reported separately (Chart I).These materials are broad-spectrum insecticides having excellent activity against the buckthorn aphid, Mexican bean beetle, southern armyworm, and the housefly. The dithia compounds and selected members of the oxathia series in addition exhibit good acaricidal potency.…”

“…The syntheses and the insecticidal properties of carbamate esters of 4-oximino-l,3-oxathiolanes (la), 3-oximino-l,4-oxathianes (lb;Kurtz et al, 1987), 4-oximino-l,3dithiolanes (Ic), and 3-oximino-l,4-dithianes (Id;D'Silva et al, 1985) have been reported separately (Chart I).…”

“…An examination of the data given for I in companion reports (D'Silva et al, 1985;Kurtz et al, 1987) reveals that the N-monomethylcarbamate compounds (I: Rx = CH3, R2 = H) are the most potent toxicants in the series. In order to focus on the role of various structural features in the oxime moiety, the compound data bank was limited to IV-monomethylcarbamates in the present study.…”