Insecticidal activity of chemical constituents from Aristolochia pubescens against Anticarsia gemmatalis larvae

Acetone and ethanol extracts of the tubercula and several compounds isolated from Aristolochia pubescens (Willd) were bioassayed on velvetbean caterpillars, Anticarsia gemmatalis (Hübner), for evaluation of the insecticidal activities. Of the extracts subjected to bioassay, the acetone extract showed the highest activity. (-)-Cubebin did not show activity against soybean caterpillars, whereas aristolochic acid and ent-kaur-15-en-17-ol increased the larval period. These compounds, and (+)-eudesmin and (+)-sesamin, reduced the viability of this period, giving rise to malformed adults. These extracts and compounds are therefore potential botanical insecticide agents for the control of velvetbean caterpillars in soybean crops.     

Isobutyl amides--potent compounds for controlling Diatraea saccharalis

BACKGROUND: A dichloromethane‐methanol extract of the seeds of Piper tuberculatum Jacq. (Piperaceae) and two isobutyl amides, 4,5‐dihydropiperlonguminine (1) and pellitorine (2), which were isolated by chromatographic methods, were assayed for their lethality against the sugarcane borer Diatraea saccharalis F. (Lepidoptera: Pyralidae). RESULTS: Bioassays were carried out with fourth‐instar caterpillars through topical application of test solutions to the dorsal surface of the prothorax, and dose–response correlations were determined. Significant insect mortalities were observed 24, 48 and 72 h after treatment at concentrations of ≥ 100 µg insect^?1. The LD₅₀ and LD₉₀ values for compound 1 were 92.83 and 176.50 µg insect^?1, and for compound 2 they were 91.19 and 184.56 µg insect^?1. CONCLUSION: According to the LD₅₀ and LD₉₀ for compounds 1 and 2, it can be inferred that the values reflect an acute lethal response to both compounds, based on interaction(s) of the toxicants with a primary target or series of targets. Thus, the amides were demonstrated to have potential value in the control of the sugarcane borer. Copyright © 2008 Society of Chemical Industry     

Insecticidal, antifeedant and oviposition deterrent effects of the essential oil and individual compounds from leaves of Chloroxylon swietenia DC

Essential oil from the leaves of Chloroxylon swietenia DC. was obtained by hydrodistillation and cold extraction, and the chemical composition was determined by gas chromatography and gas chromatography-mass spectrometry. The major identified components were limonene, geijerene, pregeijerene, germacrene D and trans-beta-ocimene. Laboratory bioassays of the essential oil and four constituents of essential oil isolates were evaluated for insecticidal, antifeedant and oviposition deterrent effects on tobacco cutworm, Spodoptera litura (F.). Toxicity was determined by topical application of the isolates at varying concentrations. Pure oil, geijerene and pregeijerene were found to be more toxic, with LD50 values of 28.6, 35.4 and 40.7 microg per larva respectively. Maximum feeding deterrence was noted for geijerene and pregeijerene, with DC(50) values of 82.5 and 95.1 microg cm(-2) respectively. Furthermore, pure oil, geijerene and pregeijerene displayed oviposition deterrence, even at low concentrations. These results indicate that these natural products may lead to useful, biodegradable, environmentally safe insect control agents.     

Effectiveness of allyl acetate as a fumigant against five stored grain beetle pests

Five esters, butyl acetate, allyl acetate, ethyl acetoacetate, isopropyl acetate and propyl acetate, were screened as fumigants in the laboratory for 24 h at 27 (+/-2) degrees C against the adults of Rhyzopertha dominica (F), Sitophilus oryzae (L) and Tribolium castaneum (Herbst). Of the compounds tested, allyl acetate was the most toxic, with LD(99) values of 7.56, 12.81 and 11.42 mg litre(-1) against R dominica, S oryzae and T castaneum, respectively. Tests with allyl acetate against mixed-age cultures of Cryptolestes ferrugineus (Stephens), Oryzaephilus surinamensis (L), R dominica, S oryzae and T castaneum revealed that doses of 50-150 mg litre(-1) with 24-120-h exposures were necessary to achieve 100% mortality of all life stages. Cryptolestes ferrugineus was the most tolerant insect tested, whilst R dominica was highly susceptible. The insect toxicity data indicates that allyl acetate has potential as a fumigant of stored food grains.     

Herbicides, glyphosate resistance and acute mammalian toxicity: simulating an environmental effect of glyphosate-resistant weeds in the USA

BACKGROUND: With the emergence of glyphosate-resistant (GR) weeds, the environmental consequences of alternatives to GR technology are of increasing importance. A well-known acute mammalian toxicity measure, the LD(50) dose for rats, is used to assess one potential environmental impact of the loss of GR technology. A new dataset with this index is used to estimate and simulate the effects for corn, soybeans and cotton.RESULTS: With conventional tillage it is found that the use of GR seeds reduces the number of LD(50) doses applied per hectare by 17-98% depending on crop. With no-till, the use of GR seeds reduces LD(50) doses only in corn. If farmers switch to conventional seeds because of GR weeds but maintain the same tillage practice, the present simulations suggest that LD(50) doses could increase by as much as 100 LD(50) doses per hectare in soybeans, and 500 LD(50) doses per hectare in cotton, or 11.4 and 19.8% respectively.CONCLUSIONS: This is the first study to use field-level data to assess GR technology with a mammalian toxicity environmental indicator. It has been found that GR crops have a positive environmental effect, and that alternatives to GR technology increase toxicity.     

Toxicity of dimethoate and fenoxycarb to honey bee brood (Apis mellifera), using a new in vitro standardized feeding method

A new in vitro method was devised to assess the effects of pesticides on honey bee brood. The method allowed the quantification of doses ingested by larvae and the assessment of larval and pupal mortality. Larval mortality in control samples was lower than 10%. Two active substances were tested: dimethoate and fenoxycarb. The LD(50) of dimethoate was 1.9 microg larva(-1) 48 h after oral exposure of larvae at day 4. Additional dose-related effects on pupal mortality were noted. After a chronic intoxication, the NOAEC (No Observed Adverse Effect Concentration) for larval mortality at day 7 was 2.5 mg kg(-1), whereas a NOAEC of 5 mg kg(-1) was found at day 22 for delayed effects on the reduction of adult emergence. Fenoxycarb applied at day 4 showed no effect on larvae, whereas emergence of adults was affected at doses higher than 6 ng larva(-1).     

Effect of azadirachtin on the control of <Emphasis Type="Italic">Anticarsia gemmatalis</Emphasis> and its impact on <Emphasis Type="Italic">Trichogramma pretiosum</Emphasis>

Anticarsia gemmatalis has great potential to reduce soybean productivity, and the egg parasitoid Trichogramma pretiosum is a major agent in the biological control of this pest in soybean fields. We show that azadirachtin is able to control velvetbean caterpillars in soybean plants and also that it has no effects on the parasitoid T. pretiosum. Soybean plants were sprayed with solutions containing control (water), 50 and 100 mg.l ⁻¹ of azadirachtin (AzaMax™ 12 g a.i.l ⁻¹). Third instar larvae of A. gemmatalis were confined to soybean plants after the spraying. Leaf consumption and larval mortality of A. gemmatalis were evaluated. Newly emerged females of T. pretiosum were placed for 24 h in tubes with a piece of cardboard containing the same doses of azadirachtin used against velvetbean caterpillars. After 24 h, cardboard with 20 eggs of A. gemmatalis was offered for parasitism during 24 h, and the emergence and sex ratio of progenies were determined. Azadirachtin at 50 or 100 mg.l ⁻¹ reduced leaf consumption and caused 100% mortality in A. gemmatalis larva. Azadirachtin did not negatively affect the parasitism, emergence or sex ratio of the progeny. This indicates that the product can be used with mass release of T. pretiosum to control A. gemmatalis.     

Effect of insect growth regulators on growth and differentiation of the tobacco caterpillarSpodoptera litura FB. (Noctuidae: Lepidoptera)

Topical application of insect growth regulators to freshly moulted sixth-instar larvae ofSpodoptera litura prevented their differentiation into pupae and resulted in the formation of a larval-pupal mosaic and of supernumerary larvae. The degree of the juvenilizing effect was dose-dependent; the doses above 20 μg produced the greatest effect, with 13.3 — 23.3% short-term mortality of treated caterpillars.     

Screening and isolation of a nematicidal sesquiterpene from Magnolia grandiflora L

The ethanolic extracts from 30 plant species were tested for their nematicidal activity against nematodes Bursaphelenchus xylophilus (Steiner & Buhrer) Nickle and Panagrellus redivivus (L.) Goodey. The leaf extract of Magnolia grandiflora L. exhibited the strongest nematicidal activity against both nematodes, causing 73 and 100% mortality respectively within 48 h at 5 mg mL(-1). A new nematicidal sesquiterpene was obtained from the leaves of M. grandiflora. The compound was determined to be 4,5-epoxy-1(10)E,11(13)-germacradien-12,6-olide, based on spectroscopic methods including 2D NMR techniques. The median lethal concentrations (LC50) of the compound against B. xylophilus and P. redivivus were 71 and 46 mg L(-1) respectively at 48 h. This is the first report of Magnoliaceae species with nematicidal activity.     

Synthesis and insecticidal activity of new amide derivatives of piperine

The natural lipophilic amides piperine and piperiline were isolated from Piper nigrum L (Piperaceae). Piperine was hydrolysed into piperic acid (85% yield) which was converted into 16 amides (28–89% yield). The contact toxicity of all synthetic amides, and also that of piperine and piperiline, at the dose 10 µg per insect, was evaluated for the Brazilian economically important insects Ascia monuste orseis Latr, Acanthoscelides obtectus Say, Brevicoryne brassicae L, Protopolybia exigua DeSaus and Cornitermes cumulans Kollar. The results demontrated that the insects have different sensivities to the various amides, with mortality ranging from 0 to 97.5% according to the compound and insect species. © 2000 Society of Chemical Industry     

Effectiveness of a naturally derived insecticide, spinosad, against the pine processionary moth Thaumetopoea wilkinsoni Tams (Lepidoptera: Thaumetopoeidae) under laboratory conditions

The pine processionary moth Thaumetopoea wilkinsoni Tams is a serious pest on pine trees in southwestern Turkey. The efficacy of a naturally derived insecticide, spinosad, on fourth-fifth instar larvae of T. wilkinsoni was studied under laboratory conditions. The product exhibited strong larvicidal activity and at doses above 5 mg litre(-1) caused > 90% mortality in the fourth-fifth larval stages of the species after 72 h. At 72 h the LD50 and LD90 values were 3.26 and 5.69 mg litre(-1) respectively. The results showed that spinosad is highly effective on T. wilkinsoni larvae.     

Effect of rotenoids from the seeds of Millettia dura on larvae of Aedes aegypti

A crude chloroform extract of seeds of Millettia dura Dunn (Leguminosae) showed high activity (LC50 = 3.5 microg ml(-1) at 24 h) against second-instar larvae of the mosquito, Aedes aegypti L (Diptera: Culicidae). The rotenoids, deguelin and tephrosin, isolated from the seeds of this plant also showed potent activities, with LC50 values of 1.6 and 1.4 microg ml(-1) at 24 h, respectively. The related rotenoids millettone and millettosin were inactive at 20 microg ml(-1). Saturation at the B/C ring junction and the presence of methoxy groups at C-2 and/or C-3 in deguelin and tephrosin appear to be important for the observed larvicidal activity.     

Learning performances of honeybees (Apis mellifera L) are differentially affected by imidacloprid according to the season

To establish the sublethal concentrations domain, acute and chronic oral tests were conducted on caged honeybee workers (Apis mellifera L) using imidacloprid and a metabolite, 5-OH-imidacloprid, under laboratory conditions. The latter showed a 48-h oral LD50 value (153 ng per bee) five times higher than that of imidacloprid (30 ng per bee). Chronic feeding tests indicated that the lowest observed effect concentrations (LOEC) of imidacloprid and of 5-OH-imidacloprid on mortality of winter bees were 24 and 120 microg kg(-1) respectively. Behavioural effects of imidacloprid and 5-OH-imidacloprid were studied using the olfactory conditioning of proboscis extension response at two periods of the year. Winter bees surviving chronic treatment with imidacloprid and 5-OH-imidacloprid had reduced learning performances. The LOEC of imidacloprid was lower in summer bees (12 microg kg(-1)) than in winter bees (48 microg kg(-1)), which points to a greater sensitivity of honeybees behaviour in summer bees, compared to winter bees.     

Laboratory and field evaluations of rhodojaponin-III against the imported cabbage worm Pieris rapae (L.) (Lepidoptera: Pieridae)

The activity of rhodojaponin-III (R-III), a grayanoid diterpene compound isolated from Rhododendron molle G. Don flowers, was determined under laboratory and field conditions as an antifeedant, stomach poison, contact toxicant and insect growth inhibitor against Pieris rapae (L.) larvae. The median antifeedant concentration (AFC(50)) values in no-choice leaf disc tests were 1.16 and 15.85 mg L(-1) at 24 h after treatment when tested against third and fifth instars respectively. The median lethal concentration (LC(50)) values in leaf disc tests were 2.84 and 9.53 mg L(-1) at 96 h after treatment against third and fifth instars respectively. R-III showed an almost 30 times higher contact toxicity against third instars than for fifth instars, and the median lethal dose (LD(50)) values for topical application were 1.18 and 34.09 mg kg(-1) at 72 h after treatment respectively. R-III disrupted the development of larvae to pupae or adults with median concentration for inhibiting growth (IC(50)) values of only 1.36 mg L(-1) for third instars and 11.28 mg L(-1) for fifth instars. In field trials, a greater than 80% reduction in the adjusted larval numbers was obtained against P. rapae 14 days after treatment when Rhodo 0.1% EC, a commercial botanical insecticide based on R-III, was applied at both 937.5 and 625 mL ha(-1). These results suggest that further research to develop R-III, and extracts from R. molle, as biorational pesticides or as lead compounds for integrated pest management deserve consideration.     

Control methods of the olive leaf gall midge (Dasineura oleae Angelini,Cecidomyiidae, Diptera) and potential implementation of integrated control programs in olive orchards

Journal of Plant Diseases and Protection - The olive leaf gall midge (Dasineura oleae) is a gall-inducing insect on leaves, branches and stems of flowers of olive trees. Heavy infestation with the...     

Synthesis and insecticidal activity of new 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives

BACKGROUND: A series of 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized as potential new agents to control insects. Their structures were confirmed on the basis of IR, NMR and MS analyses. RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl derivatives were prepared from the compound furan-2-yl N' (N,N,N',N'-tetraethyldiamidophosphate). The contact toxicity of all derivatives, at a dose of 10 microg mg(-1) insect, was evaluated against four insect species, Ascia monuste orseis Latr. (Lepidoptera: Pyralidae), Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Sitophilus zeamais Mots. (Coleoptera: Bruchidae) and Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). The mortality range observed for some derivatives, such as 3-(3-methylbenzyl)furan-2-yl N,N,N',N'-tetraethyldiamidophosphate (82.5% mortality against D. hyalinata; 100% mortality against S. saevissima), was comparable with that of the commercial insecticide chlorpyrifos-methyl. The biological activity of the derivatives depended on the substitution pattern of the benzylic ring. Furan-2-yl N,N,N',N'-tetraethyldiamidophosphate, furan-2-yl N,N-diethylamidochlorophosphate and difuran-2-yl N,N-diethylamidophosphate were also evaluated, displaying, in some cases, activity comparable with that of chlorpyrifos-methyl (90%, 100% and 97.5% respectively against A. monuste orseis). Considerable activity was observed for some furan-2(5H)-ones evaluated. CONCLUSION: Ten 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized and fully characterized from a chemical point of view. The results obtained from the biological assays indicate that this class of compounds can be utilized for the design of new substances endowed with insecticidal activity.     

Velvetbean (Mucuna pruriens) extracts: impact on Meloidogyne incognita survival and on Lycopersicon esculentum and Lactuca sativa germination and growth

Velvetbean (Mucuna spp.) is a summer annual that has been used as a cover crop to reduce erosion, fix nitrogen and suppress weeds and plant-parasitic nematodes. Crude aqueous extracts (1:15 dry weight plant/volume water) were made from velvetbean plant parts, and various concentrations of the extracts were evaluated in vitro for toxicities to different stages of Meloidogyne incognita (Kofoid and White) Chitwood and for suppression of hypocotyl and root growth and inhibition of germination of tomato (Lycopersicon esculentum L.) and lettuce (Lactuca sativa L.). Germination was only affected by the full-strength extract from leaf blades. Lettuce root growth was the most sensitive indicator of allelopathic activity of the plant part extracts. Lettuce and tomato root growth was more sensitive to the extract from main roots than to extracts of other plant parts, with lethal concentration (LC50) values of 1.2 and 1.1% respectively. Meloidogyne incognita egg hatch was less sensitive to extracts from velvetbean than the juvenile (J2) stage. There was no difference among LC50 values of the extracts from different plant parts against the egg stage. Based on LC50 values, the extract from fine roots was the least toxic to J2 (LC50 39.9%), and the extract from vines the most toxic (LC50 7.8%). The effects of the extracts were nematicidal because LC50 values did not change when the extracts were removed and replaced with water.     

Modeling insect resistance to insecticides using velvetbean caterpillar (Anticarsia gemmatalis) as an example

Evolution of insect resistance to insecticides, using the velvetbean caterpillar (Anticarsia gemmatalis) as an example, was evaluated with the help of a computer simulation model. The effects of the following factors were studied: mortality rate, dominance and initial frequency of the resistant gene, migration rate, reproductive disadvantage and action level. According to results of the model, mortality rate, genetic dominance and frequency, and insect migration were the most critical factors involved with the rate of evolution of insect resistance to insecticides. Mortality rate can be directly managed, and migration indirectly through preservation of refugia, as part of a program of resistance management, which should include insecticides with different modes of action on the insect, and at minimum efficient rates. © 1998 SCI     

Pyramiding of insecticidal compounds for control of the cowpea bruchid (Callosobruchus maculatus F.)

The cowpea bruchid (Callosobruchus maculatus F.) (Chrysomelidae: Bruchini) is a major pest of stored cowpea grain. With limited available technologies for controlling the bruchid, transgenic cowpeas with bruchid resistance genes engineered into them could become the next management tools. An investigation was made of two different sets of potential transgenic insecticidal compounds using an artificial seed system: (i) CIP-PH-BT-J and recombinant egg white avidin, and (ii) avidin and wheat alpha-amylase inhibitor. CIP-PH-BT-J (0.1%; 1000 mg kg(-1)) and recombinant egg white avidin (0.006%; 60 mg kg(-1)) incorporated separately into artificial seeds caused 98.2 and 99% larval mortality rates respectively. Combining CIP-PH-BT-J and avidin in the same artificial seed provided additional mortality compared with each factor incorporated singly; no insects survived in seeds with the combined toxins. Similarly, when avidin and wheat alpha-amylase inhibitor (alphaAI) (1%; 10 g kg(-1)) were incorporated separately into artificial seeds, this caused 99.8 and 98% mortality respectively. However, in combination, avidin and alphaAI did not increase mortality, but they did cause a significant increase in developmental time of the cowpea bruchids. These results emphasize that the joint action of potential insecticidal compounds cannot be predicted from results obtained separately for each compound, and they suggest potential transgenes for further consideration.     

Velvetbean (Mucuna spp.) suppresses speargrass (Imperata cylindrica (L.) Raeuschel) and increases maize yield

Speargrass, Imperata cylindrica (L.) Raeuschel, is a serious weed, threatening crop productivity in smallholder farms in West Africa. Since the use of more effective practices such as deep tillage and chemical control is beyond the means of resource-poor farmers who carry out most agricultural activities in this region, low-input alternative technology needs to be developed. Field studies were conducted during the 1993/1994 and 1995/1996 growing seasons to investigate the influence of three velvetbean accessions and two levels of fertilizer on the control of speargrass during the year of cover crop planting and one year later. The velvetbean accessions in 1993 were: Mucuna cochinchinensis and M. pruriens var. utilis. In 1995, M. pruriens var. IRZ was included in the study. M. cochinchinensis in 1993 and M. pruriens var. IRZ in 1995 had the highest ground cover rating early in the growing seasons whereas M. pruriens var. utilis had the lowest ground cover rating in both years. Inorganic fertilizer at30 kg ha- 1 each of N, P and K increased velvetbean ground cover by 2-22%, with M. cochinchinensis (14-22%) and M. pruriens var. IRZ (5-15%) showing the highest response in 1993 and 1995, respectively. M. pruriens var. utilis showed the least response in both years. After one growing season M. pruriens var. utilis, M. cochinchinensis, and M. pruriens var. IRZ reduced speargrass shoot density by 50, 76, and 68%, and shoot dry matter by 72, 92, and 79%, respectively. Fertilizer reduced speargrass growth in velvetbean plots, while the opposite occurred in plots without velvetbean. Velvetbean residue effectively suppressed speargrass until the beginning of the subsequent cropping season. Maize grown 1 year after velvetbean required 50% less weeding than plots without velvetbean. Maize shade reduced speargrass shoot growth by 30-80% but regrowth of the weed occurred 4 weeks before maize harvest. Maize grain yield was higher in plots previously seeded to velvetbean than in plots without velvetbean. Speargrass shoot density and dry matter were negatively correlated with maize grain yield (r =_-0.42 and r =_-0.32, respectively, P < 0.01). Although velvetbean may effectively reduce speargrass during the year of establishment and the subsequent cropping phase it has a limited effect on rhizomes and, as such, does not provide a long term control.