Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae

A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 micromol/cm2. The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED50) and a hydrogen-bonding parameter calculated from the Rf value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.     

Pyrazole derivatives as photosynthetic electron transport inhibitors: new leads and structure-activity relationship

Four series of new pyrazoles, namely, 5 4-carboxypyrazolo-3-tert-butylcarboxamide and 6 4-carboxypyrazolo-3-cyclopropylcarboxamide derivatives and 10 pyrazolo[3,4-d][1,3]thiazine-4-one and 9 pyrazolo[3,4-d][1,3]thiazine-4-thione derivatives, were synthesized and screened as potential inhibitors of photosynthetic electron transport. The structures were confirmed by 1H NMR, elemental, and IR analyses. Their biological activity was evaluated in vitro as the ability to interfere with the light-driven reduction of ferricyanide by isolated spinach chloroplasts. Only a few compounds exhibited excellent inhibitory properties in the micromolar range, comparable to those of commercial herbicides sharing the same target, such as diuron, lenacil, and hexazinone. Nevertheless, most of the remaining molecules exerted a remarkable inhibition in the millimolar range. Combined with previous results on 6 pyrazolo[1,5-a][1,3,5]triazine-2,4-dione and 4 pyrazolo[1,5-c][1,3,5]thiadiazine-2-one derivatives, these data allowed a comprehensive analysis of structure-activity relationship. Molecular modeling studies were undertaken to rationalize the structural determinants of activity in terms of shape, size, and molecular fields. Results suggested that the inhibitory potential of these compounds is associated mainly with their electrostatic properties.     

Isolation of nematicidal compounds from Tagetes patula L. yellow flowers: structure-activity relationship studies against cyst nematode Heterodera zeae infective stage larvae

Bioassay-guided isolation studies on the extracts of yellow flowers of Tagetes patula L. against the Heterodera zeae were carried out to identify phytochemicals lethal to this economically important cyst nematode. In vitro investigation of a polar extract and fractions showing activity led to the isolation of phenolic compounds (flavonoids and phenolic acids). In the nonpolar extract, a few fatty acids, their methyl esters, and thiophenes (including α-terthienyl) were detected. In studies of compounds obtained commercially, α-terthienyl and gallic and linoleic acids showed 100% mortality at concentrations of 0.125% after 24 h. Assessment of structure-activity relationships revealed that an increase in the number of hydroxyl groups in phenolic acids increased the activity; with fatty acids, activity depended on chain length and the number and position of double bonds. Crude extracts of the flowers of different colors also have promising activity.     

Changes in the levels of polymethoxyflavones and flavanones as part of the defense mechanism of Citrus sinensis (cv. Valencia Late) fruits against Phytophthora citrophthora

Phytophthora citrophthora causes serious losses in Citrus fruits through brown rot lesion. The effect of infection with P. citrophthora on Citrus sinensis (cv. Valencia Late) fruits was studied, with particular reference to the levels of the flavanones hesperidin and isonaringin and the polymethoxyflavones sinensetin, nobiletin, tangeretin, and heptamethoxyflavone, because flavonoids are most probably involved as natural defense or resistance mechanisms in this genus. Changes in the levels of these flavonoids were detected after infection. The hesperidin and isonaringin contents fell by 13 and 67%, respectively, whereas the contents of their corresponding aglycons, hesperetin and naringenin, increased, suggesting the hydrolyzing effect of this fungus on the glycosylated flavanones. The heptamethoxyflavone, nobiletin, sinensetin, and tangeretin levels increased by 48, 28, 26, and 24%, respectively. The in vitro study revealed that these compounds acted as antifungal agents, the most active being the aglycons (naringenin and hesperetin), followed by the polymethoxyflavones and flavanone glycosides. The participation of these flavonoids in the defense mechanism of this Citrus species is discussed.     

Tomato Fusarium wilt suppressiveness. The relationship between the organic plant growth media and their microbial communities as characterised by Biolog

Fusarium wilts are economically important diseases for which there are no effective chemical control measures. Biological control strategies are becoming efficient alternatives for controlling this disease. The suppressiveness to Fusarium oxysporum f. sp. lycopersici race 1 of grape marc compost and cork compost was evaluated in comparison to peat by using a susceptible cultivar of tomato (Lycopersicon esculentum cv. Marmande). Based on community level physiological profiles, different community structures were evident among the plant growth media evaluated. The peat microbial community, growth medium conducive to wilt, used mostly sugars, while those associated with both composts, the very suppressive grape marc and the moderately suppressive cork, used mostly carboxylic acids, amino acids, amines, phenolic compounds and polymers.     

Potential of Azotobacter spp. as biocontrol agents against Rhizoctonia solani and Fusarium oxysporum in cotton (Gossypium hirsutum), guar (Cyamopsis tetragonoloba) and tomato (Lycopersicum esculentum)

During the current investigation, 51 bacterial isolates/mutants of Azotobacter chroococcum, Azospirillum spp. and Gluconacetobacter diazotrophicus were tested for antifungal activity against three fungal pathogens, namely Rhizoctonia solani cotton, Rhizoctonia solani rice and Fusarium oxysporum tomato using a dual-culture technique under laboratory conditions. Ten isolates/mutants were found to be inhibitory against R. solani cotton, six against R. solani rice and twelve against F. oxysporum tomato. Nearly 50% of the isolates/mutants were siderophore positive. The antimicrobial substance was found to be extracellular and proteinaceous in nature, but in some strains it was found to be associated with other complex material also. Almost all the positive isolates/mutants showed production of antibiotic and antifungal compounds. On the basis of this study, in vitro results under laboratory conditions were reproduced in pot experiments in the greenhouse and chosen isolates/mutants of A. chroococcum were found to be effective biocontrol agents against R. solani cotton (disease index 16.7%) and R. solani rice (2.5%) in cotton crop, whereas in guar, the crop disease index was 2.5% against R. solani cotton, 13.3% against R. solani rice and 0% against F. oxysporum tomato in tomato crop compared with their respective checks.     

Changes in the Avifauna of a region, district and remnant as a result of fragmentation of native vegetation: the wheatbelt of western Australia. A case study

The wheatbelt of Western Australia is an area of about 140 000 km² which has undergone massive changes since European settlement in 1827. Clearing of native vegetation for agricultural development has removed up to 93% of the original vegetation in some areas and replaced it with exotic grasses, cereal crops and frequent watering points. The remaining vegetation is made up of thousands of remnants of various sizes, shapes and degreees of isolation scattered across the landscape.

The avifauna of the wheatbelt is examined at the regional level, the district level and at the level of the individual remnant and changes over the last 80 years or so are described. Two species of bird have gone extinct in the wheatbelt out of 148 species of land birds recorded in the region over the last 80–90 years. At the district level, more species have become extinct, the numbers depending on the extent of the removal of native vegetation and length of time since clearing took place. There is demonstrable loss of bird species at the level of the individual remnant; in the example cited (81 ha) three species have gone extinct over the last 10 years.

This rapid loss of species from district avifaunas means that remnant vegetation needs to be retained intact and conservation agencies should develop assessment techniques to identify reserve networks which include the species that have declined so that management can concentrate on them. Priorities for management should then be developed and local communities involved in the management of their local conservation systems or networks.