Insect growth inhibition,antifeedant and antifungal activity of compounds isolated/derived from Zingiber officinale Roscoe (ginger) rhizomes

Fresh rhizomes of Zingiber officinale (ginger), when subjected to steam distillation, yielded ginger oil in which curcumene was found to be the major constituent. The thermally labile zingiberene‐rich fraction was obtained from its diethyl ether extract. Column chromatography of ginger oleoresin furnished a fraction from which [6]‐gingerol was obtained by preparative TLC. Naturally occurring [6]‐dehydroshogaol was synthesised following condensation of dehydrozingerone with hexanal, whereas zingerone and 3‐hydroxy‐1‐(4‐hydroxy‐3‐methoxyphenyl)butane were obtained by hydrogenation of dehydrozingerone with 10% Pd/C. The structures of the compounds were established by ¹H NMR, ¹³C NMR and mass (EI‐MS and ES‐MS) spectral analysis. The test compounds exhibited moderate insect growth regulatory (IGR) and antifeedant activity against Spilosoma obliqua, and significant antifungal activity against Rhizoctonia solani. Among the various compounds, [6]‐dehydroshogaol exhibited maximum IGR activity (EC₅₀ 3.55 mg ml ^?1) while dehydrozingerone imparted maximum antifungal activity (EC₅₀ 86.49 mg litre^?1). © 2001 Society of Chemical Industry     

The pyrethrins and related compounds. Part XXXV. Esters of aryl-substituted cyclopentane alcohols and analogues

Synthesis of a range of 1-, 2-and 3-phenyl, benzyl and phenethyl substituted cyclopentanols and cyclopentylmethyl alcohols and related unsaturated compounds is reported. Results of bioassays of their esters with known pyrethroidal acids against two species of insect lead to recognition of some structure-activity relationships in this series. The distance and relative orientation between the alcoholic and aryl functions appears crucial, but in other respects the nature of the spacer group between them is less important. The most effective alcoholic components are based on cyclopentenes.     

The pyrethrins and related compounds. Part XXXIV. Optimisation of insecticidal activity in non-esters

Optimisation of activity within the structural constraints defined by the preceding work, by varying the substituents on phenyl in the acid fragment (10 variations), the nature of the group fulfilling the dimethyl function (three variations), the central linking group (four variations) and the presence or absence of a 4-fluoro substituent in the alcohol fragment, has led to achiral compounds as active as bioresmethrin against houseflies and mustard beetles. Statistical analysis of the effects has shown that particular combinations, for instance the cyclopropyl form of dimethyl with a central E-alkene group (but not a central ether group), lead to higher activity than expected. 4-Fluoro substitution enhances activity more strongly against mustard beetles. Difluorocyclopropyl compounds are on average slightly more active than cyclopropyl analogues.     

The pyrethrins and related compounds. Part XXVIII: Alkenyl- and alkynyl-substituted benzyl esters

Over 100 benzyl esters of pyrethroidal acids were synthesised and tested for insecticidal activity to establish detailed structure–activity relationships in compounds with side-chains similar to those in the natural pyrethrins. Alkenyl, and corresponding alkynyl, side-chains were effective, both at the 3- and 4-positions, as were side-chains with extended substitution in either E or Z forms. A cyano group at the α-position increases activity if the side-chain is at C-3, but lowers it drastically if the substituent is at C-4. Similarly, methyl groups at C-2 and/or C-6 may increase activity whether the unsaturated side-chain is at C-3 or C-4, but only in the absence of an α-cyano group.     

Use of pyrethroid analogues to identify key structural features for enhanced esterase resistance in Helicoverpa armigera (Hübner) (Lepidoptera: Noctuidae)

It has been reported previously that the major resistance mechanism to pyrethroid insecticides by the cotton bollworm Helicoverpa armigera (Hübner) in Australia is a consequence of overproduction of esterase isoenzymes. This paper reports structure-activity relationships that support such a view, based on in vivo bioassays conducted with a range of pyrethroid structures containing a variety of acid and alcohol moieties and the correlation with in vitro esterase inhibition assays against the same structures, and identifies the critical regions of the molecule with regard to esterase inhibition, and hence resistance. The implications of this work in terms of possible resistance management are evaluated and discussed.     

Chronic cryptosporidiosis in Australian elapid snakes: control of an outbreak in a captive colony

An outbreak of chronic cryptosporidiosis resulting in hypertrophic gastritis occurred in a captive colony of Australian elapid snakes. Two species of the genus Notechiswere involved: Notechis ***ater(Black Tiger Snake) and Notechis scutatus (Eastern or Mainland Tiger Snake). The infection was eventually fatal in all 9 affected snakes. Typical histopathological findings of the stomach included mucosal thickening with cystic dilatation of gastric glands, moderate oedema and fibrosis of the lamina propria, and a mild to moderate patchy infiltration of inflammatory cells. Procedures implemented to contain the outbreak included the use of a formaldehyde-based disinfectant, prompt removal of faecal matter, uneaten and regurgitated food from enclosures, and examination of faecal specimens for Cryptosporidium oocysts and other pathogens.     

The pyrethrins and related compounds. Part XXV: Synthesis and insecticidal activity of conformationally restrained compounds related to 3-phenoxybenzyl esters

Derivatives of 3-phenoxybenzyl pyrethroidal esters were synthesised in which rotation about the benzylic C-1–C-α bond was restricted by an additional bridging ring. The insecticidal activities of these compounds to houseflies (Musca dornestica) and mustard beetles (Phaedon cochleariae) depended on the size of the bridging unit and on whether it joined C-α to C-2 or C-6 of the benzyl nucleus. The results obtained are considered in relation to current correlations of the structures with the activities of pyrethroids.