Agrochemical research over the last two decades has resulted in the discovery of chemically novel insecticides that mimic the action of the two insect growth and developmental hormones, the steroidal 20-hydroxyecdysone (20E) and the sesquiterpenoid juvenile hormone (JH). Bisacylhydrazines are non-steroidal agonists of 20E and exhibit their insecticidal activity via interaction with the ecdysteroid receptor proteins. Interestingly, two of the bisacylhydrazine (tebufenozide and RH-2485) insecticides are very selectively toxic to lepidopteran pests. These insecticides are safe to beneficial insects and have a benign ecotoxicological profile. Aromatic non-terpenoidal insecticides (fenoxycarb and pyriproxyfen) mimic the action of JHs. However, like the JHs, their exact mode of action is not well understood. These insecticides are toxic to a broad spectrum of insects during their embryonic, last larval, or reproductive stages. The insecticidal, ecotoxicological properties and the mode of action of the two groups of insecticides are reviewed in this article.
aliphatic sulfinic acids in gram amounts. We have observed that the direct oxidation of aliphatic mercaptans with m-chloroperoxybenzoic acid (MCPBA) (2 equiv) in methylene dichloride yields sulfinic acids in a high state of purity and in good yield. The experimental procedure is extremely simple and was applicable, in our hands, to all paraffinic isomers in the homologous series from ethyl to butyl. Preliminary experiments have also demonstrated that the reaction proceeds cleanly in the case of the analogous system thiophenol benzenesulfinic acid.From the stoichiometry the reaction appears to proceed via the intermediate sulfinic acid RSOH, which must then undergo a preferential rapid oxidation to sulfinic acid.[O][O]This reasoning is supported by our failure to observe disulfides in the reaction products by combined mass spectral-glc analysis. The latter are reported to be disproportionation products of sulfinic acids.5
The ecdysone agonist RH 5849 (1,2-dibenzoyl-1-tert-butylhydrazine) causes the premature initiation of molting at all stages of larval development of the tobacco hornworm, Manduca sexta. This phenomenon occurs without an increase in the endogenous ecdysone (20-hydroxyecdysone) titers. RH 5849 likewise provokes the initiation of molting in larval abdomens in the absence of a source of endogenous hormone. Although substantially less active than 20-hydroxyecdysone in vitro, RH 5849 was 30 to >670 times as active as the authentic molting hormone in bioassays with isolated larval abdomens or intact hornworms. This reversal in potency can be attributed to the superior transport properties and metabolic stability of RH 5849 relative to 20-hydroxyecdysone. Thus RH 5849 and its analogs are relatively persistent ecdysone agonists that halt feeding in larval lepidoptera by forcing an ultimately lethal, developmentally premature molt.
Methoxyfenozide [N-tert-butyl-N'-(3-methoxy-o-toluoyl)-3,5-xylohydrazide; RH-2485] is the newest diacylhydrazine insecticide to reach the marketplace. It binds with very high affinity to the ecdysone receptor complex (EcR:USP) in lepidopteran insects [Kd = 0.5 nM (Plodia)], where it functions as a potent agonist, or mimic, of the insect molting hormone, 20-hydroxyecdysone (20E). Methoxyfenozide exhibits high insecticidal efficacy against a wide range of important caterpillar pests, including many members of the family Pyralidae, Pieridae, Tortricidae and Noctuidae. It is most effective when ingested by the target caterpillar, but it also has some topical and ovicidal properties. It is modestly root systemic, but not significantly leaf-systemic. Evidence collected to date indicates that methoxyfenozide has an excellent margin of safety to non-target organisms, including a wide range of non-target and beneficial insects.
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