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Cotton bollworm (Helicoverpa armigera) is a Lepidopteran noctuid pest with a global distribution. It has a wide range of host plants and can harm cotton, tomato, tobacco, and corn, as well as other crops. H. armigera larvae damage the flower buds, flowers, and fruits of tomato and cause serious losses to tomato production. Tomato uses the allelochemical 2-tridecanone to defend against this damage. So far, there have been no reports on whether the adaptation of H. armigera to 2-tridecanone is related to its symbiotic microorganisms. Our study found that Corynebacterium sp. 2-TD, symbiotic bacteria in H. armigera, mediates the toxicity of the 2-tridecanone to H. armigera. Corynebacterium sp. 2-TD, which was identified by 16S rDNA gene sequence analysis, was screened out using a basal salt medium containing a unique carbon source of 2-tridecanone. Then, Corynebacterium sp. 2-TD was confirmed to be distributed in the gut of H. armigera by quantitative PCR (qPCR) and fluorescence in situ hybridization (FISH). The survival rate of H. armigera increased by 38.3% under 2-tridecanone stress after inoculation with Corynebacterium sp. 2-TD. The degradation effect of Corynebacterium sp. 2-TD on 2-tridecanone was verified by ultra-high-performance liquid chromatography (UPLC). Our study is the first to report the isolation of gut bacteria that degrade 2-tridecanone from the important agricultural pest H. armigera and to confirm bacterial involvement in host adaptation to 2-tridecanone, which provides new insights into the adaptive mechanism of agricultural pests to host plants. [ABSTRACT FROM AUTHOR]

Cotton bollworm (Helicoverpa armigera) is a Lepidopteran noctuid pest with a global distribution. It has a wide range of host plants and can harm cotton, tomato, tobacco, and corn, as well as other crops. H. armigera larvae damage the flower buds, flowers, and fruits of tomato and cause serious losses to tomato production. Tomato uses the allelochemical 2-tridecanone to defend against this damage. So far, there have been no reports on whether the adaptation of H. armigera to 2-tridecanone is related to its symbiotic microorganisms. Our study found that Corynebacterium sp. 2-TD, symbiotic bacteria in H. armigera, mediates the toxicity of the 2-tridecanone to H. armigera. Corynebacterium sp. 2-TD, which was identified by 16S rDNA gene sequence analysis, was screened out using a basal salt medium containing a unique carbon source of 2-tridecanone. Then, Corynebacterium sp. 2-TD was confirmed to be distributed in the gut of H. armigera by quantitative PCR (qPCR) and fluorescence in situ hybridization (FISH). The survival rate of H. armigera increased by 38.3% under 2-tridecanone stress after inoculation with Corynebacterium sp. 2-TD. The degradation effect of Corynebacterium sp. 2-TD on 2-tridecanone was verified by ultra-high-performance liquid chromatography (UPLC). Our study is the first to report the isolation of gut bacteria that degrade 2-tridecanone from the important agricultural pest H. armigera and to confirm bacterial involvement in host adaptation to 2-tridecanone, which provides new insights into the adaptive mechanism of agricultural pests to host plants.

Alcohol dehydrogenase 5 (ADH5) is a member of medium‐chain dehydrogenase/reductase family and takes part in cellular formaldehyde and S‐nitrosoglutathione metabolic network. 2‐tridecanone (2‐TD) is a toxic compound in many Solanaceae crops to defend against a variety of herbivory insects. In the broader context of insect development and pest control strategies, this study investigates how a new ADH5 from Helicoverpa armigera (HaADH5) regulates the expression of CYP6B6, a gene involved in molting and metamorphosis, in response to 2‐TD treatment. Cloning of the HaADH5 complementary DNA sequence revealed that its 1002 bp open reading frame encodes 334 amino acids with a predicted molecular weight of 36.5 kD. HaADH5 protein was purified in the Escherichia coli Transetta (pET32a‐HaADH5) strain using a prokaryotic expression system. The ability of HaADH5 protein to interact with the 2‐TD responsive region within the promoter of CYP6B6 was confirmed by an in vitro electrophoretic mobility shift assay and transcription activity validation in yeast. Finally, the expression levels of both HaADH5 and CYP6B6 were found to be significantly decreased in the midgut of 6th instar larvae after 48 h of treatment with 10 mg/g 2‐TD artificial diet. These results indicate that upon 2‐TD treatment of cotton bollworm, HaADH5 regulates the expression of CYP6B6 by interacting with its promoter. As HaADH5 regulation of CYP6B6 expression may contribute to the larval xenobiotic detoxification, molting and metamorphosis, HaADH5 is a candidate target for controlling the growth and development of cotton bollworm. [ABSTRACT FROM AUTHOR]

Aphis gossypii , a globally distributed and economically significant pest of several crops, is known to infest a wide range of host plants. Heat shock proteins (Hsps), acting as molecular chaperones, are essential for the insect's environmental stress responses. The present study investigated the molecular characteristics and expression patterns of AgHsp70 , a heat shock protein gene, in Aphis gossypii. Our phylogenetic analysis revealed that AgHsp70 shared high similarity with homologs from other insects, suggesting a conserved function across species. The developmental expression profiles of AgHsp70 in A. gossypii showed that the highest transcript levels were observed in the fourth instar nymphs, while the lowest levels were detected in the third instar nymphs. Heat stress and exposure to four different xenobiotics (2-tridecanone, tannic acid, gossypol, and flupyradifurone (4-[(2,2-difluoroethyl)amino]-2(5 H)-furanone)) significantly up-regulated AgHsp70 expression. Knockdown of AgHsp70 using RNAi obviously increased the susceptibility of cotton aphids to 2-tridecanone, gossypol and flupyradifurone. Dual-luciferase reporter assays revealed that gossypol and flupyradifurone significantly enhanced the promoter activity of AgHsp70 at a concentration of 10 mg/L. Furthermore, we identified the transcription factor heat shock factor (HSF) as a regulator of AgHsp70 , as silencing AgHSF reduced AgHsp70 expression. Our results shed light on the role of AgHsp70 in xenobiotic adaptation and thermo-tolerance. [Display omitted] • One heat shock protein, named AgHsp70 , was identified in the cotton aphid. • Under thermal stress, only heat significantly upregulated the AgHsp70 expression. • AgHsp70 was responsible to 2-tridecanone, gossypol and flupyradifurone. • The promoter activity was significantly enhanced by gossypol and flupyradifurone. • AgHsp70 was possibly regulated by AgHSF via RNAi method. [ABSTRACT FROM AUTHOR]

The expression level of cytochrome P450 genes in insects can be induced by plant allelochemicals, which is important for insects to adapt to host plants. Cytochrome P450 CYP6B7 has been reported to be involved in pyrethroid insecticide resistance in Helicoverpa armigera, and its transcription level was induced by some inducers. Currently, the regulatory mechanism of the induced expression of CYP6B7 remains unknown, although it is very important for understanding the detoxification mechanism to allelochemicals in host plants. The objective of the present study was to investigate the cis‐acting element in the promoter of CYP6B7 mediating the inducible up‐regulation of CYP6B7 in H. armigera by 2‐tridecanone. The promoter region of CYP6B7 was cloned by genome walking technique and analyzed by transient transfection assay. Progressive 5′ deletion of the promoter region of CYP6B7 revealed that the relative luciferase activity of construct −320/+232 could be significantly induced by 2‐tridecanone. Further stepwise deletion between −320 and −238 bp found that construct −292/+232 could also be significantly induced by 2‐tridecanone, but the adjacent construct −256/+232 could not, suggesting the essential role of the sequence between −292 and −257 bp for 2‐tridecanone induction. Nucleotide mutations between −292 and −281 bp had no influence on the induction effect by 2‐tridecanone, but nucleotide mutations between −280 and −257 bp significantly decreased the induction effect. These results demonstrated that the cis‐acting element for 2‐tridecanone induction was between −280 and −257 bp in the promoter of CYP6B7. [ABSTRACT FROM AUTHOR]

The lone star tick, Amblyomma americanum, is a vector of several important human and animal diseases. This tick species has rapidly expanded in its geographic distribution, and its aggressive behavior has increased the risk of tick-borne diseases in these new areas. Repellents are recommended by the Centers for Disease Control and Prevention (CDC) for protection against tick bites. DEET is the most common repellent, but public concerns over its safety have increased the need for alternative safe and efficacious tick repellents. Several naturally derived animal compounds have been tested against other species of ticks or other arthropod pests, but not against A. americanum. Based on EC50 values obtained using a vertical paper bioassay, decylamine and MT-710 (a 2-tridecanone formulation) were found to be as repellent as DEET. Those two substances along with 2-tridecanone were also found to be as repellent as DEET when their EC95 values were compared. Lone star ticks were more susceptible to the toxic effects of DEET in glass vial assays than all of the ant-derived defensive compounds/formulations. These results suggest that the ant-derived defensive compounds are likely more effective lone star tick repellents than DEET, but they are not as toxic as DEET towards the ticks. The suitability of these compounds for use as personal repellents, as well as at the landscape scale, should be explored. [ABSTRACT FROM AUTHOR]

P-glycoprotein (P-gp) exists in animals, fungi and bacteria and likely evolved as a defense mechanism against harmful substances. Here a cDNA (4054 bp) encoding a putative P-glycoprotein gene from Helicoverpa armigera was cloned and named HaPgp1 . This putative HaPgp1 sequence encoded a protein of 1253 amino acids with a molecular mass of approximately 137 kDa. qPCR analyses demonstrated that the expression of HaPgp1 was significantly higher in 4th instar larvae when compared to other developmental stages. HaPgp1 transcripts were more abundant in the head and fat bodies than in other tissues. Compared with the control, the expression of HaPgp1 reach a peak at 12 h after the treatment by 2-tridecanone in all tissues. However, the expression of HaPgp1 increased from 12 h to 48 h after treatment with abamectin in all tissues. Immunohistochemistry analyses also verified that 2-tridecanone and abamectin can induce the increase of HaPgp1 expression. RNAi of HaPgp1 significantly raised the mortality rate of larvae treated by 2-tridecanone and abamectin, as compared to control larvae fed with GFP dsRNA. These results illustrate the possible involvement of HaPgp1 as a component of the protective mechanisms to plant secondary chemicals such as 2-tridecanone and to certain classes of insecticides, like abamectin. [ABSTRACT FROM AUTHOR]

The aim of the study was to investigate volatile compounds from the aerial parts of Dianthus acicularis of the genus Dianthus of the family Caryophyllaceae grown wild in Northern Kazakhstan for the first time. D. acicularis is a typical Trans-Volga-Kazakhstani endemic. D. acicularis has high resistance to the bacterial wilt, a serious disease caused by Burkholderia caryophylli. The qualitative and quantitative compositions of the specimens of the essential oils were analysed by the method of GC–MS. The main constituents of D. acicularis essential oil were methyl ketones - 2-pentadecanone (26.9–32.2%) and 2-tridecanone (4.7–17.7%), identified for the first time in the Dianthus genus. The methyl ketone activity provides protection of the plants from herbivores and fungal pathogens. One can suppose that the presence of 2-pentadecanone and 2-tridecanone in the essential oil of carnation coniferous provides its resistance to different insects and pathogens, including the resistance to the bacterial wilt. [ABSTRACT FROM AUTHOR]

In Brazil, the tomato is cultivated in almost all geographic regions even though its yield is significantly reduced by pests and diseases. Among these pests and diseases, whitefly is a major problem that causes direct and indirect damage due to its role in transmission of geminiviruses. The aim of the present study was to compare the degree of resistance to the silverleaf whitefly of tomato plant lines rich in acyl sugars (AS), zingiberene (ZGB), and 2-tridecanone (2-TD) and to establish whether selection for strains with higher densities of glandular trichomes promotes sufficient resistance to this insect pest. The investigated lines were developed by performing back-crossings in tomato (Solanum lycopersicum) from the interspecific crossing of S. lycopersicum x S. habrochaites var. glabratum 'PI 134417'. Lines rich in AS, ZGB, and 2-TD were tested for their levels of resistance to B. tabaci biotype B. Two tomato plant lines (TOM-584 and TOM-679) with normal AS levels and one wild specimen (PI 134417) with high 2-TD content were used as controls. TOM-687, ZGB-703, and TOM-622 were less preferred by B. tabaci for oviposition, and nymphs exhibited a poorer survival rate on those plant lines than on the susceptible controls, TOM-584 and TOM-679. Allelochemical-rich lines exhibited pest resistance, whereas the controls did not, and the allelochemical-rich lines did not differ significantly from each other in the level of resistance. The results show that the development of tomato plant lines rich in 2-TD, ZGB and AS is an effective option for indirect selection for resistance to B. tabaci biotype B. All lines selected based on high trichome density except for BPX-365F-751-05-01-03 exhibited fewer nymphs than the susceptible controls, indicating that selection for more glandular trichomes was generally effective in promoting increased resistance to the silverleaf white flay.No Brasil, o tomate é cultivado em praticamente todas as regiões, embora seu rendimento seja reduzido por pragas e doenças. A mosca-branca, comumente presente, causa danos diretos e indiretos, devido à transmissão de geminiviros. O objetivo do presente trabalho foi comparar o grau de resistência à mosca branca de linhagens de tomateiro ricas em acilaçúcares (AA), zingibereno (ZGB) e 2-tridecanona (2-TD) e verificar se a seleção de linhagens com base em tricomas glandulares é efetiva no sentido de promover níveis satisfatórios de resistência. Essas linhagens foram obtidas através de retrocruzamentos em tomateiro Solanum lycopersicum, a partir do cruzamento interespecífico S. lycopersicum x S. habrochaites var. glabratum 'PI 1344171'. Linhagens ricas em AA , ZGB e 2-TD foram testadas para níveis de resistência. Duas linhagens de tomateiro (TOM-584 e TOM-679), com nível normal de AA, e o acesso selvagem (PI 134417), alto teor de 2-TD, foram utilizados como testemunhas. TOM-687, ZGB-703 e TOM-622 mostraram diminuições na ovoposição e na contagem de ninfas, quando comparados com os controles TOM-584 e TOM-679. As linhagens ricas nos aleloquímicos mostraram níveis de resistência à praga, relativamente aos controles, e não deferiram significativamente entre si. Os resultados mostram que linhagens ricas em AA, ZGB e 2-TD são eficazes alternativas de seleção indireta para criação de resistência a Bemisia argentifolii. As linhagens selecionadas para maior densidade de tricomas, exceto BPX-365F-751-05-01-03, apresentaram números médios de ninfas inferiores ao das testemunhas suscetíveis, indicando que a seleção para maior número de tricomas glandulares foi efetiva no sentido de promover aumento dos níveis de resistência à mosca-branca.

The objective of this work was to evaluate the feasibility of selection for higher glandular trichome densities, as an indirect criterion of selection for increasing repellence to spider mites Tetranychus urticae, in tomato populations derived from an interspecific cross between Lycopersicon esculentum x L. hirsutum var. glabratum PI 134417. Trichome densities were evaluated in 19 genotypes, including 12 from advanced backcross populations, derived from the original cross L. esculentum x L. hirsutum var. glabratum PI 134417. Counts were made both on the adaxial and abaxial leaf surfaces, and trichomes were classified into glandular types IV and VI, other glandular types (types I+VII), and nonglandular types. Mite repellence was measured by distances walked by mites onto the tomato leaf surface after 20, 40 and 60 min. Spider mite repellence biotests indicated that higher densities of glandular trichomes (especially type VI) decreased the distances walked by the mites onto the tomato leaf surface. Selection of plants with higher densities of glandular trichomes can be an efficient criterion to obtain tomato genotypes with higher resistance (repellence) to spider mites.O objetivo deste trabalho foi avaliar a eficiência da seleção para maior densidade de tricomas glandulares na resistência (repelência) ao ácaro Tetranychus urticae, em populações de tomate derivadas do cruzamento interespecífico Lycopersicon esculentum x L. hirsutum var. glabratum PI 134417. Foram avaliados 19 genótipos quanto à densidade de tricomas, que incluíram 12 derivados de populações avançadas de retrocruzamentos, obtidos a partir do cruzamento original L. esculentum x L. hirsutum var. glabratum PI 134417. Nas faces abaxial e adaxial dos folíolos, realizaram-se as contagens e os tricomas foram classificados em glandulares tipo IV e VI, outros glandulares (tipo I e VII) e não glandulares. A repelência aos ácaros foi medida pela distância média, percorrida pelo ácaro na superfície do folíolo de tomateiro, após 20, 40 e 60 min. Os biotestes de repelência ao ácaro rajado demonstraram que a alta densidade de tricomas glandulares, especialmente de tipo VI, influencia negativamente a distância média percorrida pelos ácaros na superfície do folíolo. Plantas com número de tricomas glandulares elevado podem ser selecionadas para se obterem genótipos com alto índice de repelência aos ácaros.

The effect of 2-tridecanone vapor on the cowpea weevil (Callosobruchus maculatus) development was determined. Seeds of cowpea were infested with adults and exposed to different doses of 2-tridecanone isolated from Pilocarpus microphyllus Stapf ex Holm, a plant species native from northeastern Brazil. The pure monoterpene was evaluated both undiluted as well as in the dilutions 1:10, 1:100 and 1:1,000 (v/v). The following parameters of the cowpea weevil life cycle were analyzed in response to decreasing doses of 2-tridecanone: number of eggs laid, percentage of egg hatching on seeds, percentage of adult emergence, adult weight at emergence, mean developmental time and number of adults emerged. Vapor of 2-tridecanone caused a significant (P < 0.05) reduction in the number of eggs laid, in the percentage of eggs hatched and in the number of emerged adults in infested seeds. The fumigant insecticidal effect of 2-tridecanone was mainly due to its ovicidal activity.O efeito dos vapores da 2-tridecanona sobre o caruncho do feijão-de-corda (Callosobruchus maculatus) foi avaliado. Sementes de feijão-de-corda infestados com insetos adultos foram expostas a diferentes doses de 2-tridecanona isolada de Pilocarpus microphyllus, uma espécie nativa do Nordeste do Brasil. O monoterpeno puro foi utilizado nas diluições 1:10, 1:100 e 1:1000 (v/v). Os parâmetros da biologia do inseto foram analisados em função da resposta a doses decrescentes de 2-tridecanona: número de ovos postos por fêmea, percentagem de eclosão de ovos, percentagem de emergência de adultos, peso dos adultos recém-emergidos, tempo médio de desenvolvimento e número total de ovos emergidos. Diferenças significativas (P < 0.05) entre as doses de 2-tridecanona testadas foram observadas, para quatro dos seis parâmetros biológicos analisados. Os resultados obtidos indicaram que a 2-tridecanona é tóxica para C. maculatus, reduzindo significativamente (P < 0.05) o número de insetos emergidos após a infestação. Esse efeito foi causado principalmente pela significativa redução observada na eclosão dos ovos expostos ao vapor da substância.

In insect, the cytochrome P450 plays a pivotal role in detoxification to toxic allelochemicals. Helicoverpa armigera can tolerate and survive in 2-tridecanone treatment owing to the CYP6B6 responsive expression, which is controlled by some regulatory DNA sequences and transcription regulators. Therefore, the 2-tridecanone responsive region and transcription regulators of the CYP6B6 are responsible for detoxification of cotton bollworm. In this study, we used yeast one-hybrid to screen two potential transcription regulators of the CYP6B6 from H. armigera that respond to the plant secondary toxicant 2-tridecanone, which were named Prey1 and Prey2, respectively. According to the NCBI database blast, Prey1 is the homology with FK506 binding protein (FKBP) of Manduca sexta and Bombyx mori that belongs to the FKBP-C superfamily, while Prey2 may be a homology of an unknown protein of Papilio or the fcaL24 protein homology of B. mori. The electrophoretic mobility shift assays revealed that the FKBP of prokaryotic expression could specifically bind to the active region of the CYP6B6 promoter. After the 6th instar larvae of H. armigera reared on 2-tridecanone artificial diet, we found there were similar patterns of CYP6B6 and FKBP expression of the cotton bollworm treated with 10 mg g−1 2-tridecanone for 48 h, which correlation coefficient was the highest (0.923). Thus, the FKBP is identified as a strong candidate for regulation of the CYP6B6 expression, when the cotton bollworm is treated with 2-tridecanone. This may lead us to a better understanding of transcriptional mechanism of CYP6B6 and provide very useful information for the pest control. [ABSTRACT FROM AUTHOR]

The essential oils of the leaves and fine stems of Pilocarpus microphyllus, collected on iron mineralized soil of the Serra de Carajás, Southeast of Pará State, Brazil, during the rainy and dry seasons, were obtained by hydrodistillation and analyzed by GC-MS. The main identified compounds were 2-tridecanone, beta-caryophyllene, 2-pentadecanone, caryophyllene oxide and germacrene D. Their percentage contents varied with the season, the greater values having been detected mainly in the rainy season. For 2-tridecanone and beta-caryophyllene the higher values were observed in the fine stem oils for the former, and in the leaf oils for the latter. For 2-pentadecanone, caryophyllene oxide and germacrene D they were also in the leaf oils. In general, the leaf oils were very distinguishable from those of fine stem oils, even in the same specimen.Os óleos essenciais das folhas e galhos finos de Pilocarpus microphyllus, coletado em solo mineralizado com ferro, na Serra de Carajás, Sudeste do Pará, Brasil, durante as estações chuvosa e seca, foram obtidos por hidrodestilação e analisados por GC-MS. Os principais compostos identificados foram 2-tridecanona, beta-cariofileno, 2-pentadecanona, óxido de cariofileno e germacreno D. Seus teores percentuais variam com a estação, embora os maiores valores tenham sido detectados principalmente na estação chuvosa. Para 2-tridecanona e beta-cariofileno os valores mais expressivos foram observados nos óleos de galhos finos, para o primeiro, e nos óleos das folhas, para o útimo. Para 2-pentadecanona, óxido de cariofileno e germacreno D, os valores mais altos foram, também, nos óleos das folhas. Em geral, os óleos das folhas se apresentaram muito distintos em relação aos galhos finos, assim como também no mesmo espécime.

BACKGROUND In our screening programme for new agrochemicals from wild plants, the essential oil of Tetradium glabrifolium (Champ. ex Benth.) T.G. Hartley fruits was found to possess strong larvicidal activity against the Asian tiger mosquito, Aedes albopictus L. The essential oil was extracted via hydrodistillation, and the constituents were determined by GC-MS analysis. The active compounds were isolated and identified by bioassay-directed fractionation. RESULTS GC-MS analyses revealed the presence of 19 components with 2-tridecanone (43.38%), 2-undecanone (24.09%), D-limonene (13.01%), caryophyllene (5.04%) and β-elemene (4.07%) being the major constituents. Bioactivity-directed chromatographic separation of the oil led to the isolation of 2-tridecanone, 2-undecanone and D-limonene as active compounds. The essential oil of T. glabrifolium exhibited larvicidal activity against the early fourth-instar larvae of A. albopictus, with an LC50 value of 8.20 µg mL−1. The isolated constituent compounds, 2-tridecanone, 2-undecanone and D-limonene, possessed strong larvicidal activity against the early fourth-instar larvae of A. albopictus, with LC50 values of 2.86, 9.95 and 41.75 µg mL−1 respectively. CONCLUSION The findings indicated that the essential oil of T. glabrifolium fruits and the three constituents have an excellent potential for use in control of A. albopictus larvae and could be useful in the search for newer, safer and more effective natural compounds as larvicides. © 2014 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

A new invader, the 'tawny crazy ant', Nylanderia fulva (Hymenoptera: Formicidae; Formicinae), is displacing the red imported fire ant, Solenopsis invicta (Formicidae: Myrmicinae), in the southern U.S., likely through its superior chemical arsenal and communication. Alone, formic acid is unattractive, but this venom (= poison) acid powerfully synergizes attraction of tawny crazy ants to volatiles from the Dufour's gland secretion of N. fulva workers, including the two major components, undecane and 2-tridecanone. The unexpected pheromonal synergism between the Dufour's gland and the venom gland appears to be another key factor, in addition to previously known defensive and detoxification semiochemical features, for the successful invasion and domination of N. fulva in the southern U.S. This synergism is an efficient mechanism enabling N. fulva workers to outcompete Solenopsis and other ant species for food and territory. From a practical standpoint, judicious point-source release formulation of tawny crazy ant volatiles may be pivotal for enhanced attract-and-kill management of this pest. [ABSTRACT FROM AUTHOR]

The full-length c DNA (2320 bp) encoding a putative iron-binding transferrin protein from Helicoverpa armigera was cloned and named Ha Trf. The putative Ha Trf sequence included 670 amino acids with a molecular mass of approximately 76 kDa. Quantitative PCR results demonstrated that the transcriptional level of Ha Trf was significantly higher in the sixth instar and pupa stages as compared with other developmental stages. Ha Trf transcripts were more abundant in fat bodies and in the epidermis than in malpighian tubules. Compared with the control, the expression of Ha Trf increased dramatically 24 h after treatment with 2-tridecanone. Apparent growth inhibition with a dramatic body weight decrease was observed in larvae fed with Ha Trf double-stranded RNA (ds RNA), as compared with those fed with green fluorescent protein ds RNA. RNA interference of Ha Trf also significantly increased the susceptibility of larvae to 2-tridecanone. These results indicate the possible involvement of Ha Trf in tolerance to plant secondary chemicals. [ABSTRACT FROM AUTHOR]

Estudos foram conduzidos com o objetivo de verificar o efeito de tricomas, aleloquímicos e nutrientes nas folhas de partes do dossel das plantas na resistência de Lycopersicon hirsutum à traça- do-tomateiro, Tuta absoluta (Lepidoptera: Gelechiidae). Foram quantificados os teores de 2-tridecanona (2-TD), 2-undecanona (2-UD), N, P, K, Ca e Mg, densidade e tipos de tricomas e tamanho das folhas nos terços apical, mediano e basal do dossel de plantas de L. hirsutum e de L. esculentum e estudaram- se os efeitos destes fatores sobre características biológicas de T. absoluta. Observou-se elevação no teor de 2-TD da base para o ápice do dossel. Não se detectou diferença significativa quanto ao número de ovos de T. absoluta ao longo do dossel de L. hirsutum, constatando-se em L. esculentum maior oviposição nos terços apical e mediano do que no basal. As folhas do terço apical de L. hirsutum apresentaram maior efeito deletério sobre as larvas de traça.The objective of this work was to study the effect of trichomes, alellochemicals and minerals in the leaves of different canopy heights on the resistance of Lycopersicon hirsutum to tomato leaf miner, Tuta absoluta (Lepidoptera: Gelechiidae). Effects of 2-tridecanone (2-TD), 2-undecanone (2-UD), N, P, K, Ca and Mg levels, density and types of trichomes and leaf area on apical, medium and basal parts of plant dossel of L. hirsutum and L. esculentum on the oviposition and mines number of T. absoluta was studied. Production of 2-TD increased from the bottom to the top of the canopy. The apical part of plants of L. hirsutum showed more antibiotic effect on the caterpillar. T. absoluta oviposited more on leaves of the apical and medium portion of the plants than in the basal parts of L. esculentum.

Abstract: Nylanderia fulva (Mayr) has been reported as being able to displace Solenopsis invicta Buren, one of the most aggressive invasive ants in the world. Like S. invicta, N. fulva use chemical secretions in their defense/offense, which may contribute to their observed superior competition ability. In this study, the defensive chemicals of N. fulva workers and their toxicity against S. invicta workers were investigated. Like other formicine ants, N. fulva workers produce formic acid in their poison glands and 2-ketones and alkanes in Dufour glands. Of these, undecane and 2-tridecanone are two principal compounds in the Dufour gland. Topical LD50 values of 2-tridecanone and undecane against S. invicta workers ranged from 18.51 to 24.67 μg/ant and 40.39 to 84.82 μg/ant, respectively. Undecane and 2-tridecanone had significantly higher contact toxicity than formic acid, whereas formic acid had significantly higher fumigation toxicity than undecane and 2-tridecanone. The combination of 2-tridecanone as a contact toxin and formic acid as a fumigant significantly decreased KT50 values when compared to those of individual compounds. N. fulva does not seem unique in terms of the chemistry of its defensive secretion as compared to other formicine ants. However, this ant contained more than two orders of magnitude of formic acid (wt/wt) than other formicine ants and one order of magnitude of 2-tridecanone than the common crazy ant, Paratrechina longicornis (Latreille). The quantity, rather than quality, of the chemical secretion may contribute to the superior competition ability of N. fulva. [Copyright &y& Elsevier]

Abstract: The p-nitroanisole O-demethylase activity of P450s and expression of CYP6B6 mRNA induced by two plant secondary substances, 2-tridecanone and quercetin, were investigated in cotton bollworm, Helicoverpa armigera (Hübner). The O-demethylase activity was higher in the fat body than that in the midgut of the sixth-instar larvae fed on the artificial diets mixed with these allelochemicals. The similar results were obtained when induced by the combination of 2-tridecanone and quercetin at different concentrations. When the concentration of inducers, mixture of 2-tridecanone and quercetin, was 0.5mg/ml in the diet, the maximum O-demethylase activities of P450 in the midgut and fat body were 2.6 and 3.88 times higher than those in the relevant control, respectively. Specific primers were designed according to the CYP6B6 and an actin gene of cotton bollworm and used to determine the expression level of CYP6B6 mRNA in the midgut and fat body by a reverse transcription-polymerase chain reaction (RT-PCR) method. The expression levels of CYP6B6 mRNA were obviously correlated with the concentrations of 2-tridecanone, but no correlation with the concentrations of quercetin. When induced with the mixture of 2-tridecanone and quercetin at a concentration of 0.5mg/ml in the diet, the maximum expression amount of CYP6B6 mRNA in the midgut and fat body was induced, which was 1.74 and 1.8 times compared with the corresponding control, respectively. It suggests that the cytochrome P450 has an important role in the metabolism of plant secondary substances in cotton bollworm. [Copyright &y& Elsevier]

Wild tomato leaves possess a pest-resistance mechanism in their glandular trichomes and the exudates they produce. Type IV and VI glandular trichomes on the leaves of five wild tomato accessions of Lycopersicum hirsutum f. glabratum (PI 126449, PI 134417, PI 134418, PI 251304, and LA 407) grown under greenhouse conditions were counted. Major chemical compounds from glandular leaf trichomes of the accessions tested were extracted, purified, and quantified at different periods during the growing seasons by gas chromatography (GC) and mass spectrometry (GC/MS). The toxicity of two methylketones (2-undecanone and 2-tridecanone), the major constituents of the accessions tested, to adults of the sweetpotato whitefly, Bemisia tabaci (Gennadius) and fourth instar larvae of the Colorado potato beetle (CPB), Leptinotarsa decemlineata (Say), was determined using no-choice bioassays. 2-undecanone caused 80% mortality of the fourth instar larvae of the CPB at the highest concentration tested (100 mg 2-undecanone mL - 1 of acetone) while 2-tridecanone caused 72% mortality of whiteflies at 20 mg 2-tridecanone mL - 1 of 65% ethanol. The concentration of 2-undecanone and 2-tridecanone on the leaves of each of the five accessions of L. hirsutum f. glabratum and the mass spectra of 2-undecanone and 2-tridecanone are presented. Overall, the concentration of 2-undecanone on the leaves was significantly higher than 2-tridecanone. Concentration of the two methylketones varied among accessions and sampling season. Plants produced the highest concentration of 2-undecanone during the month of August. On average, each plant of accession PI 251304 provided 354 g fresh leaves (averaging about 52,353 cm 2 exposed leaf surface area) and produced 32.5 and 8.7 mg of 2-undecanone and 2-tridecanone, respectively. L. hirsutum f. glabratum accessions may become a valuable source of natural products, which could minimize reliance on synthetic pesticides. [ABSTRACT FROM AUTHOR]

Elevated atmospheric CO2 concentrations ([CO2]) have been hypothesized to increase photosynthesis rates and volatile organic compound (VOC) emissions; however, field measurements from a select group of conifer and angiosperm trees have shown that VOC emissions are in fact not affected or reduced by elevated CO2 levels. To broaden the understanding of how different plant species respond to elevated atmospheric [CO2], air-flow-through, glass chambers were designed and utilized to measure photosynthesis and emissions from onion (Allium cepa cv. ‘Purplette’) under controlled environmental conditions. Here we report on VOC release and root exudation while monitoring photosynthesis from whole plants grown under ambient (400 μmol mol−1) and elevated (1000 μmol mol−1) [CO2]. A 22% increase in photosynthesis in the elevated CO2 plants and a 17-fold and 38-fold increase in the VOC hydrocarbons 2-undecanone and 2-tridecanone, respectively, were observed in 30-day-old onion seedlings compared to plants grown under ambient CO2 conditions. In contrast TOC from root exudates decreased significantly with elevated CO2 conditions. Plants harvested at 30 days had on average over 40% greater biomass when grown at elevated CO2 levels. The demonstration that VOC emissions increase in plants grown under elevated [CO2] and higher photosynthesis rates points to a fundamental difference in how carbon partitioning alters in herbaceous species such as onion versus the previously studied tree species in response to elevated concentration of atmospheric CO2. [Copyright &y& Elsevier]

Abstract 1 Field experiments were performed in barley using volatile semiochemicals affecting population density (density-related substances – DRS) and spring migration (methyl salicylate) in bird cherry oat aphid Rhopalosiphum padi (L.). Natural infestations of aphids were used, and semiochemical dosages were chosen to be biologically relevant based on previous studies. A simple formulation method for active substances using wax pellets was developed. 2 The effect of treatments on aphid populations was analysed in terms of initial colonization of the crop, temporal dynamics of the population and maximum aphid incidence. 3 Treatments caused a significant delay in aphid establishment in the crop, and reduced the average infestation by 25–50% compared with the untreated control. At a moderate attack rate, the treatments with methyl salicylate and DRS gave a significant reduction in maximum aphid numbers. 4 The significant control effect of the treatment encourages further investigation both to increase understanding of the ecological role of the active substances, and to establish the limitations for their use in plant protection. [ABSTRACT FROM AUTHOR]

Production of methyl ketones as naturally occurring insecticides from wild tomato accessions is explored in this study. Density of two glandular trichomes (type IV and type VI) on the leaves of six wild tomato accessions of Lycopersicon hirsutum f. glabratum (Mull); three accessions of L. hirsutum f. typicum (Humb & Bonpl.); two accessions of L. pennellii Corr. (D'Arcy); and density of type VI glandular trichomes of the commercial tomato Lycopersicon esculentum cv. Fabulous are reported. Densities of type IV and VI glandular trichomes varied among the accessions tested. Type IV trichomes occurred at much higher densities than type VI. Over all accessions and counting trichome densities on both abaxial and adaxial leaflet surfaces, type IV densities averaged 96,378 trichomes.g[sup -1] leaflets while type VI densities averaged 67,350 trichomes.g[sup -1] leaflets. Concentrations of four methyl ketones (2-tridecanone, 2-dodecanone, 2-undecanone, 2-pentadecanone) were determined per unit leaf surface area (mm²) and per g fresh leaflets. Concentrations of total methyl ketones ranged from 81.3 µg. g[sup -1] fresh leaflets on L. esculentum cv. Fabulous to 5.5 mg. g[sup -1] on L. hirsutum f. glabratum (PI 134417). Two methyl ketones, 2-undecanone and 2-tridecanone, predominated trichome secretions in five of the L. hirsutum f. glabratum accessions tested (PI 251304, PI 126449, PI 134417, PI 134418, and LA 407). [ABSTRACT FROM AUTHOR]

Volatiles in leaf extracts of Lycopersicon hirsutum f. glabratum disrupted settled Macrosiphum euphorbiae and caused 100% mortality over 24 hr. There was a single peak of activity among fractions separated by silica gel column chromatography. 2-Tridecanone was the major component of all active fractions, and responses to 2-tridecanone alone were similar to the initial extract. Another major component, 2-undecanone had no effect on M. euphorbiae either alone or as a synergist of 2-tridecanone. Trichome exudates and 2-tridecanone applied to artificial membranes inhibited feeding and caused mortality over 24 hr. Topical LD50 for 2-tridecanone was 1.0 μg/individual. The lab colony displayed little variation in susceptibility to 2-tridecanone. The effectiveness of 2-tridecanone in reducing infestation by M. euphorbiae and evidence of behavioral resistance in M. euphorbiae to 2-tridecanone are discussed. [ABSTRACT FROM AUTHOR]

The essential oil of the fresh plant of Spilanthes acmella Murr. from southern India was investigated by GC and GC/MS. More than 45 components have been identified including (E)-2-hexenol (25.7%), 2-tridecanone (13.1%), germacrene D (11.1%), hexanol (11.0%), β-caryophyllene (10.8%) and (Z)-3-hexenol (5.1%) as significantly dominating compounds. Additional components, responsible for the characteristic aroma impressions of this sample are especially C6-C9 derivatives, mono- and sesquiterpenes. [ABSTRACT FROM AUTHOR]

Despite there being a number of excellent studies on detoxification enzyme-mediated interaction between insect and plant allelochemical, there are no reports on the pathway of the transferrin effect in insect response to host plant allelochemical. Our research indicates that Helicoverpa armigera transferrin ) inhibited the apoptotic cell death treated by 2-tridecanone, a host plant allelochemical present in tomato species ( HaTrf ) inhibited the apoptotic cell death treated by 2-tridecanone, a host plant allelochemical present in tomato species ( Lycopersicon hirsutum f. glabratum ), by cellular redox-related transcription factor nuclear factor erythroid-2-related factor 2 ( Nrf2 ). Nrf2 inhibited the apoptotic cell death during exposure to host plant allelochemical 2-tridecanone and provides a novel view on transferrin and its anti-apoptotic role in plant-insect interactions.HaTrf inhibited the apoptotic cell death during exposure to host plant allelochemical 2-tridecanone and provides a novel view on transferrin and its anti-apoptotic role in plant-insect interactions.