Behavioural observations of Pieris brassicae larvae indicate multiple mechanisms of action of analogous drimane antifeedants

We tested 11 analogous synthetic drimane antifeedant compounds for their feeding inhibiting effects on larvae of the large white butterfly Pieris brassicae L. (Lepidoptera: Pieridae) in no-choice tests on the host plant Brassica oleracea L. Furthermore, we observed larval feeding behaviour in no-choice tests to analyze temporal effects of five drimanes. The results show that the five analogous antifeedants differentially influence feeding behaviour and locomotion activity. Warburganal and polygodial are most likely sensory mediated antifeedants. Habituation to these compounds occurs soon after the onset of the tests (i.e., within 0.5–1.5 h). Compound 5 and confertifolin are probably not direct, sensory mediated antifeedants. After 0.5–1.5 h of exposure, these compounds inhibit not only feeding, but also locomotion behaviour, indicating postingestive, toxic effects. Isodrimenin inhibits feeding from the onset of the test and is probably a sensory mediated antifeedant. No habituation occurs to this compound, indicating that isodrimenin is either a very strong antifeedant or that it additionally has postingestive, toxic effects. Topical application of the drimanes on the larval cuticle revealed feeding inhibiting effects, but these could not be related to the occurrence of postingestive feeding inhibiting effects, indicating that this method is inappropriate to show possible postingestive effects of drimanes in P. brassicae. In conclusion, the behavioural observations performed in this research indicate that analogous drimanes inhibit feeding by P. brassicae larvae through multiple mechanisms of action. The results show that, when developing a structure activity relationship (SAR) for a series of antifeedants, it is important to distinguish the mode of action which underlies inhibition of feeding.     

Antifeedant C20 diterpene alkaloids

We have tested the insect antifeedant and toxic activity of 21 C20 diterpenoid alkaloids on Spodoptera littoralis and Leptinotarsa decemlineata. The antifeedant effects of the test compounds were structure- and species-dependent. The most active antifeedants to L. decemlineata and S. littoralis were the rearranged form of hetisine (20; EC50 = 1.7 microg/cm2) and 19-oxodihydroatisine (9; EC50 = 0.1 microg/cm2), resp. Glandulosine (8) moderately affected orally injected S. littoralis larvae. A few compounds (13-oxocardiopetamine (4), 9, and atisinium chloride (13)) had cytotoxic effects to insect-derived Sf9 cells with varying degrees of selectivity with respect to mammalian CHO cells. Compounds 4 and 15,22-O-diacetyl-19-oxodihydroatisine (10) increased Trypanosoma cruzi mortality. Our results support the plant protective role of C20 diterpenoid alkaloids and open a new field for parasite control strategies.     

Selection of Beauveria bassiana (Bals.) Vuill. and Metarhizium anisopliae (Metsch.) Sorok. isolates against Alphitobius diaperinus (Panzer) (Coleoptera: Tenebrionidae)

This study was carried out to evaluate entomopathogenic fungi isolates as microbial control agents ofthe lesser mealworm, Alphitobius diaperinus (Panzer). Larvae and adults were inoculated with conidial suspension of 99 isolates of Beauveria bassiana (Bals.) Vuill. and Metarhizium anisopliae (Metsch.) Sorok. (10(5) to 10(9) conidia/ml). Vegetative growth on culture media and sporulation on culture media, cooked rice and lesser mealworm cadavers were also evaluated. Isolates of B. bassiana were more effective than the M. anisopliae isolates and larvae were more susceptible than adults. The isolates UNIOESTE 04 and UNIOESTE 02 were originally obtained from adults of the lesser mealworm and were the most efficient isolates. In addition, UNIOESTE 04 showed high level of sporulation on different culture media and is considered a potential useful tool to lesser mealworm control.     

Toxicity of mycotoxins of Fusarium sambucinum for feeding in Galleria mellonella

Fusarium sambucinum Fuckel showed antifeedant activity towards larvae of Galleria mellonella L. when incorporated into insect diet. The activity appeared mostly due to the concentration of trichothecenes present in the fungal extracts. Diacetoxyscirpenol and neosolaniol showed similar levels of activity and were significant potent antifeedants against larvae at 50 and 100 ppm. On the contrary, enniatin B showed no activity up to 100 ppm.     

Antifeedant activity and toxicity of two alkaloids from Adhatoda vasica Nees leaves against diamondback moth Plutella xylostella (Linn.) (Lepidoptera: Plutellidae) larvae

Two natural alkaloids viz., Vasicine acetate and 2-Acetyl benzylamine, isolated from Adhatoda vasica leaves, showed antifeedant, larvicidal and moult inhibiting properties against diamondback moth Plutella xylostella in laboratory experiments. Maximum antifeedant activity of 98.5% was recorded at 1000 ppm concentration of Vasicine acetate treatment, whereas as 2-Acetyl benzyl amine recorded only 71.4% antifeedant activity at 1000 ppm concentration. Azadirachtin treatment presented 82% antifeedant activity at the highest concentration (1000 ppm). Both the active compounds of A. vasica showed lethal toxicity on larvae and pupae. The highest larvicidal and pupicidal activities were recorded in 2-Acetyl benzylamine treatment at 125 ppm concentration. The two A. vasica compounds also affected the normal growth and development and moulting process of P. xylostella. Final moulting of larvae into pupae was disrupted by the treatments, which resulted in larval–pupal intermediates and abnormal pupae. Treatments also produced small-size pupae and malformed adults with poorly developed wings.     

Susceptibility of Alphitobius diaperinus (Coleoptera: Tenebrionidae) from broiler facilities in Texas to four insecticides

Lesser mealworm, Alphitobius diaperinus (Panzer) (Coleoptera: Tenebrionidae), adults were collected from six eastern Texas broiler facilities and examined for susceptibility to four formulated insecticides. Data indicate that A. diaperinus adults exposed to filter papers treated with the label rates of the insecticides exhibit some level of recovery. Approximately 20% or less A. diaperinus adults treated with Tempo SC Ultra (8 ml/92.9 m2, 11.8% beta-cyfluthrin) or Talstar WP Insecticide/Miticide (23.3 ml/92.9 m2, 10% bifenthrin) and recorded as moribund at the 4-h observation period recovered by the 24-h observation period. A. diaperinus adults treated with Tempo SC Ultra and Talstar WP also had the greatest percentage of mortality for both observation periods. A. diaperinus adults treated with Dragnet SFR (49.7 ml/92.9 m2, 36.8% permethrin) had the greatest level of recovery at approximately 50-60% overall, which was similar to that recorded for the water-only control. Additionally, five of the six A. diaperinus populations treated with Dragnet SFR resulted in < 10% mortality for both observation periods. Unlike the other insecticides examined, Talstar Professional Insecticide (10 ml/92.9 m2, "Talstar Pro," 7.9% bifenthrin) resulted in approximately 50% more A. diaperinus mortality at the 24-h than the 4-h observation period due primarily to increased mortality recorded for Farm F. A. diaperinus adults from farm D had > or = 87% knockdown 4 h after treatment to all compounds examined, indicating a high degree of sensitivity to these compounds. However, approximately 90% of the A. diaperinus adults from this population treated with Dragnet SFR and recorded as moribund recovered by the 24-h observation. A. diaperinus adults from this population treated with the other insecticides exhibited limited recovery. Susceptible adult A. diaperinus populations are still present in Texas, based on the populations examined. But, identifying these populations is difficult and time-consuming. Consequently, screening populations before treatment might not be feasible. However, newer generation pyrethroids examined in this study seem to be suitable for suppressing A. diaperinus populations in broiler facilities.     

Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety

The antifeedant activity of a series of lignan lactones, hemiacetals, ethers, and alcohols derived from yatein and cubebin, together with structurally related phenylpropanoids and phenolics possessing a methylenedioxyphenyl (piperonyl) moiety, was tested against selected stored products pests: Sitophilus granarius L. (Coleoptera: Curculionidae), Tribolium confusum Duv. (Coleoptera: Tenebrionideae), and Trogoderma granarium Ev. (Coleoptera: Dermestridae). The relation between molecular structure and antifeedant activity was examined and implication of the piperonyl moiety is assessed. The compounds represent either natural substances isolated from plants (Libocedrus yateensis Guillaumin and Piper cubeba L.) or their structural analogues prepared by simple chemical transformations as well as compounds selected from commercially available sources. Natural lignan lactones with methoxy and/or methylenedioxy substituents showed significant activity that is strong enough to affect plant - insect interactions. Presence of polar substituents, especially hydroxy or glycosyl groups, often reduce the activity. Non-polar substituents, such as methoxy or methylenedioxy groups, enhance the activity not only in lignans but also in simple phenylpropanoids. The most active compound was synthetic piperonylbutoxide.     

Constituents of glandular trichomes of Tithonia diversifolia: relationships to herbivory and antifeedant activity

The herbivory activity of the bordered patch larvae (Chlosyne lacinia, Lepidoptera) on leaves of a Brazilian population of Tithonia diversifolia and the antifeedant potential of its leaf rinse extract were investigated. The caterpillars fed only on the adaxial face, where the density of glandular trichomes is very low, and avoided the abaxial face, which contains high levels of trichomes. Deterrent activity against the larvae was observed in leaf discs treated with leaf rinse extract at concentrations of 1-5% of fresh leaf weight. High-performance liquid chromatography (HPLC) analysis indicated that sesquiterpene lactones are the main constituents of the glandular trichomes. Dichloromethane rinse extracts of the leaves and inflorescences were chemically investigated, and 16 compounds were isolated and identified: 14 sesquiterpene lactones, a flavonoid and a diterpenoid. In this study, five sesquiterpene lactones are described for the first time in the genus, including two lactones, one of which has an unusual seco-guaianolide skeleton. Our findings indicate that the caterpillars avoid the sesquiterpene-lactone-rich glandular trichomes, and provide evidence for the antifeedant activity of the dichloromethane leaf rinse extract. In addition, a study of the seasonal variation of the main constituents from the leaf surface throughout a year demonstrated that a very low qualitative but a very high quantitative variation occurs. The highest level of the main metabolite tagitinin C was observed between September and October and the lowest was from March to June, the later corresponding to the period of highest infestation by the larvae.     

BIOACTIVITIES AND MECHANISM OF SPIRO ENOL ETHER ANALOGUES AGAINST PIERIS RAPAE

Abstract  Nineteen kinds of spiro enol ether analogues were screened with larvae of Pieris rapae for antifeedant activity. The results showed that the antifeedant activity of compounds No.20 and No. 12 was higher than others. In non-choice test, AFC50 values within 24 h of compounds No.20 and No. 12 against 3rd instar larvae of P. rapae were 226.93 μg/mL and 370.00 μg/mL, and that in choice test against 4th larvae were 280.54 μg/mL and 398.88 μg/mL, respectively. Compd. No.20 could prolong the eggs hatch time and reduce the haemolymph content and the protein content in haemolymph of 4th instar larvae obviously. Compd. No.20 could protect tested leaves and control larvae of P. rapae effectively.     

Antifeedant and phytotoxic activity of hydroxyperezone and related molecules

The insect antifeedant and toxic activity of hydroxyperezone (1), its derivatives 2-9, along with 3-hydroxy- (10) and 6-hydroxythymoquinone (11) were studied against Spodoptera littoralis, Leptinotarsa decemlineata, and Myzus persicae. The antifeedant tests showed that L. decemlineata was the most sensitive insect, followed by M. persicae, while S. littoralis was not deterred by compounds 1-11. Leucohydroxyperezone tetraacetate (3), oxoperezinone (6), dihydroleucoperezinone diacetate (7), 3-hydroxy- (10) and 6-hydroxythymoquinone (11) showed strong activity against L. decemlineata. 1 and 7 exhibited moderate deterrent activity against M. persicae, while 1 and dihydroleucohydroxyperezone tetraacetate (4) acted as post-ingestive antifeedants to S. littoralis. The phytotoxic activity of compounds 1-11 was also evaluated. Hydroxyperezone (1) strongly inhibited seed germination at 24 h, while the activity of 3-8 and 10 was moderate. The level of radicle growth inhibition obtained with compounds 1-5 and 8-11 was significant (< 50%).     

Antifeedant properties and chemotaxonomic implications of sesquiterpene lactones and syringin from Rhaponticum pulchrum

From aerial parts of Rhaponticum pulchrum the guaiane-type sesquiterpene lactones aguerin B, janerin, 19-deoxyjanerin, chlorojanerin, 15-dechloro-15-hydroxychlorojanerin, cynaropicrin, cebellin G, repdiolide and repensolide were isolated, together with the phenylpropanoid glucoside syringin. In no-choice and two-choice feeding experiments aguerin B, chlorojanerin and syringin were shown to be good antifeedants against the three species of the stored product insect pests Sitophilus granarius, Trogoderma granarium and Tribolium confusum, while janerin and cynaropicrin inhibited feeding of the latter species. However, the highest antifeedant activity was recorded for the extract of the plant enriched in sesquiterpene lactones. The unexpected finding was that syringin inhibited feeding of the insects.     

New butenolides from the photoconductivity screening of Streptomyces antibioticus (Waksman and Woodruff) Waksman and Henrici 1948

Abstract Streptomyces antibioticus strain TÜ 99, from which a wide variety of active compounds had been isolated previously, was reinvestigated using an HPLC photoconductivity screening system. Four new compounds were isolated, characterized and their constitutions determined. All four were α,β-unsaturated γ-lactones; the most abundant compound 3 (C₁₀H₁₆O₄), as well as compound 1 (C₉H₁₄O₄) had a hydroxy group at C(5) of the lactone ring. The four lactones showed antibiotic activity against Pseudomonas aeruginosa and also a weak inhibition of the chitinase from Serratia marcescens .     

Antifeeding activity of limonoids from Khaya senegalensis (Meliaceae)

Abstract: Fifteen B,D-secolimonoids of mexicanolide, rearranged phragmalin, methyl angolensate and glycoside types have been isolated from ether and acetone extracts of the stem bark of Khaya senegalensis (Desr.). The antifeedant activity of the isolated compounds was assessed by conventional choice leaf disc method on the third-instar larvae of Spodoptera littoralis (Boisd.). Khayalactol, 1- O -acetylkhayanolide A, 2-hydroxyseneganolide, khayanolide A, khayanolide D and methyl angolensate displayed strong antifeedant activity at 1000  μ g/ml with antifeedant percentages of 83.8, 61.9, 60.1, 59.5, 57.1 and 55.7, respectively. 2-Hydroxyseneganolide and khayanolide D showed high activity at 500, 300 and 200  μ g/ml while 1- O -acetylkhayanolide A was the only compound that revealed antifeedant activity at a concentration as low as 100  μ g/ml. Antifeedant activity was dose-dependent in some of the isolated compounds. Correlation between antifeedant activity of the isolated compounds and chemical structure was discussed.     

Phytochemicals and Insect Control: An Antifeedant Approach

Plants based pest control agents have long been touted as alternatives to synthetic chemicals for integrated pest management. Such phytochemicals reputedly pose little threat to the environment or to human health. Bioactivity of plant-based compounds is well documented in literature and is a subject of increasing importance. An antifeedant approach for insect control has been extensively studied, at least at laboratory level, though only a handful of plant-based compounds are currently used in agriculture. The known active plant-based antifeedants belong to groups like chromenes, polyacetylenes, saponins, quassinoids, cucurbitacins, cyclopropanoid acids, phenolics, alkaloids, various types of terpenes and their derivatives etc., and each insect species may process these allomones in a thoroughly idiosyncratic way, so that the same compound may have very different fates and consequences in different species of insects, thus pointing to different mechanisms involved in antifeedant action. It can also be visualized that insect feeding deterrents may be perceived either by stimulation of specialized deterrent receptors or by distortion of the normal function of neurons, which perceive phagostimulating compounds. Some plant antifeedants influence the feeding activity through a combination of these two principal modes of action. Only a few highly active antifeedants have been looked into from a commercial point of view, which makes it impossible to systemize or to predict any molecular motifs in feeding inhibition. Structure activity relationship studies also do not point to any generalization. “Mix and Match” systems may help in developing a cocktail of feeding inhibitors that can be used in developing a customized formulation against a specific category of pests. Application of such products will be broad and will not be limited to targeted pests and to plant parts. Decreased deterrence resulting from habituation has been suggested that could pose different implications for pest management than does decreased deterrence resulting from increased tolerance to toxic substances. Genetically modified plants, which could produce the active antifeedant substances in amounts high enough to protect the plants from further herbivorous damage, could be a possibility in the future.     

植物源昆虫拒食活性物质的研究和应用

植物在与昆虫协调进化过程中形成了许多具有防御功能的次生代谢物质。作者对近年来植物源昆虫拒食活性物质的研究和应用进行了综述,其结构类型主要涉及萜类、生物碱类、酚类等,讨论了制约植物源昆虫拒食剂发展的因素并展望了植物源昆虫拒食剂在未来害虫综合治理中的作用。     

Evaluation of a barrier to inhibit lesser mealworm (Coleoptera: Tenebrionidae) and dermestidae movement in high-rise, caged-layer poultry facilities

An evaluation of a mechanical barrier to prevent movement of adult and larval lesser mealworm, Alphitobius diaperinus (Panzer); larder beetle, Dermestes lardarius L.; and hide beetle, Dermestes maculatus De Geer was conducted in caged-layer poultry facilities in New York and Maine. The barrier, a plastic collar wrapped around building support posts, proved highly effective at preventing movement of adult lesser mealworms. Significantly more lesser mealworm larvae were recovered from cardboard collar beetle traps placed below both washed and unwashed barriers than from traps placed above washed and unwashed barriers. Similarly, significantly more adult Dermestes were recovered from traps placed below washed barriers than from above both washed and unwashed barriers. The level of fly specking on the barrier was found to have no significant impact on the numbers of adult lesser mealworms and adult and larval Dermestes recovered either above or below barriers. Fly specking level did significantly impact the numbers of lesser mealworm larvae recovered above the barrier. Although washed barriers provided the greatest deterrent to adult lesser mealworms, the presence of the barrier, regardless of the level of fly specking, provided a significant deterrent to beetle climbing success. Washed barriers further reduced climbing success by lesser mealworm larvae by 17%, Dermestes adults by 7-28%, and Dermestes larvae by 33-38%. The high level of climbing observed by adult lesser mealworms suggests that the impact of adult beetle movement toward birds should be considered in its importance in building damage, disease transmission, feed infestation, and bird productivity and health. Observations on cost and maintenance of the barrier are discussed.     

Behavioural and neurophysiological responses ofSpodoptera littoralis to azadirachtin and a range of synthetic analogues

The antifeedant activity of azadirachtin and 56 azadirachtin analogues, including 22,23-dihydroazalirachtin, against larvae ofSpodoptera littoralis was investigated using behavioural and electrophysiological bioassays. None of the analogues was as active as azadirachtin, although many showed significant antifeedant activity at high concentrations. The majority of the analogues stimulated a dose-dependent response from a neurone in the medial styloconic maxillary sensilla which correlated with the behavioural activity. Methylation of the hydroxy substitutions on the azadirachtin molecule usually resulted in a decrease in antifeedant activity, as did the addition of bulky groups to the dihydrofuran ring.     

Insect antifeedant activity of clerodane diterpenes and related model compounds

A comprehensive compilation of all test results on the insect antifeedant activity of clerodane diterpenes and related model compounds is reported. To increase the compatibility of data from different sources, some of the results reported in the literature have been converted into a standardized form. The compounds were sorted into groups according to the different types of sidechain attached to C-9. Despite the wealth of information, collected in 15 tables, it remains difficult to assign importance to separate structural elements in relation to the observed antifeedant activity. A detailed analysis of the structure-activity relationships could not be presented, but some interesting trends can be distinguished based on the structures of the strongest antifeedants. The compilation covers the literature up to December 2001.     

Populational fluctuation and spatial distribution of Alphitobius diaperinus (Panzer) (Coleoptera; Tenebrionidae) in a poultry house, Cascavel, Parana state, Brazil.

Knowledge of the population fluctuation and spatial distribution of pests is fundamental for establishing an appropriate control method. The population fluctuation and spatial distribution of the Alphitobius diaperinus in a poultry house in Cascavel, in the state of Parana, Brazil, was studied between October, 2001 and October 2002. Larvae and adults of the lesser mealworm were sampled weekly using Arends tube traps (n = 22) for six consecutive flock grow-outs. The temperature of the litter and of the poultry house was measured at the same locations of the tube traps. Beetle numbers increased continuously throughout all the sampling dates (average 5,137 in the first week and 18,494 insects on the sixth week). Significantly greater numbers of larvae were collected than adults (1 to 20 times in 95% of the sampling points). There was no correlation between temperature and the number of larvae and adults collected, therefore no fluctuation was observed during the sampling period. The population growth was correlated to litter re-use. The highest temperatures were observed in deep litter. The spatial distribution of larvae and adults in the poultry house was heterogeneous during the whole period of evaluation. Results suggest that monitoring in poultry houses is necessary prior to adopting and evaluating control measures due to the great variability of the insect distribution in the poultry house.     

Distribution of enantiomers of volatile organic compounds in selected fruit distillates

The enantiomer ratios of chiral volatile organic compounds in fruit distillates were determined by multidimensional gas chromatography using solid‐phase microextraction (SPME) as a sample treatment procedure. Linalool and its oxides, limonene, α‐terpineol, and nerolidol, were present at the highest concentration levels, while significantly lower amounts of β‐citronellol and lactones were found in the studied samples. However, almost all terpenoids mainly occur as a racemic or near‐racemic mixture; enantiomer distribution of some chiral organic compounds in fruit distillates correlated to a botanical origin. In particular, a significant enantiomeric excess of (R)‐linalool and (S)‐α‐terpineol was found only for pear brandy, and likewise the dominance (R)‐limonene and the second eluted enantiomer of nerolidol for Sorbus domestica and strawberry, respectively. The distribution of γ‐lactones stereoisomers was more nonspecific, with a general excess of the R‐enantiomer.