Compounds from Ageratum conyzoides: isolation, structural elucidation and insecticidal activity

This work aimed at identifying plant compounds with insecticidal activity against Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Musca domestica (L.) (Diptera: Muscidae), Periplaneta americana (L.) (Blattodea: Blattidae) and Rhyzopertha dominica (F.) (Coleoptera: Bostrichidae). The plant species used were: basil (Ocimum selloi Benth.), rue (Ruta graveolens L.), lion's ear (Leonotis nepetaefolia L.), Jimson weed (Datura stramonium L.), 'baleeira' herb (Cordia verbenaceae L.), mint (Mentha piperita L.), wild balsam apple (Mormodica charantia L.) and billy goat weed (Ageratum conyzoides L.). Firstly, the insecticidal activities of hexane and ethanol plant extracts were evaluated against adults of R. dominica. Among them, only the hexane extract of A. conyzoides showed insecticidal activity. The hexane extract of this plant species was therefore fractionated by silica gel column chromatography to isolate and purify its bioactive chemical constituents. Three compounds were identified using IR spectra, (1)H NMR, (13)C NMR, HMBC and NOE after gel chromatography: 5,6,7,8,3', 4', 5'-heptamethoxyflavone, 5,6,7,8,3'-pentamethoxy-4', 5'-methylenedioxyflavone and coumarin. The complete assignment of (13)C NMR to 5,6,7,8,3'-pentamethoxy-4', 5'-methylenedioxyflavone was successfully made for the first time. 5,6,7,8,3'-Pentamethoxy-4', 5'-methylenedioxyflavone did not show any insecticidal activity against the four insect species tested. 5,6,7,8,3', 4', 5'-Heptamethoxyflavone showed low activity against D. hyalinata and R. dominica and was not toxic to M. domestica or P. americana. In contrast, coumarin showed insecticidal activity against all four insect pest species tested, with the following order of susceptibility: R. dominica < P. americana < D. hyalinata < M. domestica after 24 h exposure.     

Imidacloprid mobility and longevity in soil columns at a termiticidal application rate

The mobility, longevity and termiticidal activity of imidacloprid (Premise 2 termiticide; Bayer Environmental Sciences) at the termiticidal labeled rate for perimeter treatment were tested in vegetated and non-vegetated soil columns in two tests: in cone plots and in polyvinyl chloride (PVC) pipes. Imidacloprid content in the cone plot eluate peaked at 1 month, declined rapidly by the second month and then entered a lagging phase. The concentration of imidacloprid in the cone plot soil declined from 84.5 microg g(-1) initially to 7.5 microg g(-1) (non-vegetated plots) and 8.1 microg g(-1) (vegetated plots) 6 months later. Neither eluate concentration nor soil concentration was affected by the presence of vegetation in the cone plots. In the PVC pipes, the top 15 cm of which was treated with Premise 2 at the perimeter labeled rate, imidacloprid half-life was estimated at 6-9 months for vegetated and non-vegetated soil. Extractable imidacloprid declined more rapidly in the first 15 months than afterwards. Mobility of imidacloprid into lower, untreated soil depths was higher in non-vegetated pipes, and was likely due to the effect of vegetation on soil moisture. The presence of vegetation had little effect on the termiticidal activity of treated soil in the PVC pipes.     

Per os efficacy of Ajuga extracts against sucking insects

We studied the efficacy of water-soluble extracts from four Ajuga spp on the post-embryonic development of two exopterygota (sucking insect) species. To allow comparison between different Ajuga species, results are expressed in terms of quantity of plant extracted per litre of test solution. Crude methanolic extracts of all Ajuga plants tested, with the exception of A genevensis, showed considerable per os efficacy against larvae of both Dysdercus cingulatus F and Acyrthosiphon pisum (Harris) even at 1 g litre(-1). In the aphid tests the order of efficacy was A bracteosa Wallich ex Benth > A chamaepitys Schreber > A reptans L > A genevensis L. On D cingulatus the order of efficacy was: A reptans > A bracteosa > A chamaepitys > A genevensis. Extracts were fractionated on SepPak using a range of methanol/water mixtures. Results are expressed in terms of the initial weight of plant extracted. The 100% methanolic fraction of A chamaepitys was highly effective on A pisum (100% mortality at 1 g litre(-1)) and less effective on D cingulatus (about 60% mortality at 5 g litre(-1)). The entire 60 methanol + 40 water fraction was effective against test insects but showed different efficacies according to test species and concentration applied. 20-Hydroxyecdysone (20E), cyasterone (Cy) and ajugalactone (Ajl) were identified in the fractions from all Ajuga species, but the remaining phytoecdysteroid profile was quite different between Ajuga species. Capitasterone (Cap) and 28-epi-sengosterone (5Cy28') were found only in A reptans, makisterone A (MaA) and 29-norcyasterone (29NCy) were only in A chamaepitys, while 22-acetylcyasterone (Cy22A), 3-epi-cyasterone (Cy') and 3-epi-22-acetylcyasterone (Cy'22A) were only in A bracteosa. The total amount of phytoecdysteroids was 2053 mgkg(-1) for A bracteosa, 1892 mgkg(-1) for A reptans and 95 mg kg(-1) for A chamaepitys.     

Inhibitory activity against plant pathogenic fungi of extracts from Myoporum bontioides A. Gray and indentification of active ingredients

BACKGROUND: In order to understand the bioactivity of Myoporum bontioides A. Gray against plant pathogens and determine its active ingredients, the inhibitory activities of methanol extracts from M. bontioides against Fusarium oxysporum f. sp. niveum (E. F. Smith) Snyder & Hansen, Pestalotia mangiferae P. Henn., Thielaviopsis paradoxa (De Seynes) v. Hohnel, Colletotrichum musae (Berk. & M. A. Curtis) v. Arx, Alternaria alternata (Fr.) Keissler, Mycosphaerella sentina (Fr.) Schroter and Sphaceloma fawcettii Jenk. were evaluated using a growth rate method, and the active ingredient was isolated by activity-directed isolation and identified by determination and analysis of IR, (1)H NMR, (13)C NMR and mass spectra and correlative physical constants. RESULTS: The results showed that the extracts from stems and leaves of M. bontioides exhibited inhibitory activity against the seven fungi, with > 58% inhibition at 10 g L(-1) after 72 h. The active compound was isolated and identified as (-)-epingaione, and showed inhibitory activity against the above seven fungi. The inhibitory activity against P. mangiferae was the highest, with an EC(50) value of 77 mg L(-1). The EC(50) values against the other six fungi were 147-245 mg L(-1). (-)-Epingaione also inhibited spore germination of F. oxysporum f. sp. niveum, T. paradoxa and S. fawcettii.CONCLUSION: (-)-Epingaione demonstrated broad-spectrum inhibitory activity against plant pathogenic fungi and is promising for exploitation as a fungicide.     

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.     

The termiticidal activity of Sextonia rubra (Mez) van der Werff (Lauraceae) extract and its active constituent rubrynolide

BACKGROUND: Termites are degradation agents that inflict severe damage on wood. Some long‐lasting Amazonian trees can resist these insects by producing toxic secondary metabolites. These metabolites could potentially replace synthetic termiticidal products which are becoming more restricted to use. RESULTS: Sextonia rubra is resistant to termite‐induced degradation. It has been demonstrated that this species naturally produces an ethyl‐acetate‐soluble termiticidal metabolite, rubrynolide, to protect its wood. Assays in the presence of tropical and invasive termites established that both rubrynolide and crude ethyl acetate extract from S. rubra wood can be used as a treatment for the protection of sensitive woods against termites. CONCLUSION: Rubrynolide and S. rubra extract are promising candidates for the replacement of synthetic termiticides. Copyright © 2011 Society of Chemical Industry     

加工番茄叶霉病的防治药剂筛选及其品种抗性鉴定

本研究针对加工番茄叶霉病菌进行了药剂室内毒力测定和盆栽防效试验,并对14份加工番茄品种抗叶霉病进行了评价,目的是筛选出对加工番茄叶霉病具有良好防效的药剂和抗病品种。结果表明:30%烯酰·咪鲜胺SC抑菌效果最好,其EC50为0.006mg/mL。防效试验中,5种药剂均有一定的抑菌效果;22.5%异菌脲SC、56.7%氢氧化铜WG、47%春雷王铜WP和30%烯酰·咪鲜胺SC对叶霉病的防效均在60%以上。供试的14份加工番茄品种中,没有发现高抗品种,中抗品种4个,感病品种8个,高感品种2个。‘屯河9号’、‘石红666’、‘金红宝87-5’和‘737’为中抗品种,‘石红18’和‘石红45’为高感品种,其余为感病品种。     

Studies on Endophytic Actinomycetes ( I ) <Emphasis Type="Italic">Streptomyces </Emphasis>sp. Isolated from Rhododendron and Its Antifungal Activity

To survey endophytic actinomycetes as potential biocontrol agents against fungal diseases of rhododendron, young plants of rhododendron were surface-sterilized for use as an isolation source. Nine, six and two isolates, with distinguishing characteristics based on the macroscopic appearance of colonies, were obtained from roots, stems and leaves, respectively, suggesting that various species of actinomycetes grow in the respective organs of this plant as symbionts or parasites. On an agar medium, only isolate R-5 commonly formed a clear growth-inhibition zone against two major fungal pathogens of rhododendron, Phytophthora cinnamomi and Pestalotiopsis sydowiana, indicating that this isolate can produce antifungal material(s). Acetone extracts of a liquid culture of R-5 had a broad antimicrobial spectrum against Gram-positive bacteria, yeast and filamentous fungi. Isolate R-5 was identified as a Streptomyces sp. based on morphological, physiological and chemotaxonomical characteristics. The present results indicate that isolate R-5 is a suitable candidate for the biocontrol of diseases of rhododendron. Received 25 March 2000/ Accepted in revised form 18 May 2000     

α[3-(2,2-二氯乙烯基)-2,2-二甲基环丙基甲酰氧基烷基]膦酸酯的合成及生物活性研究

以二氯菊酰氯和α-羟基烃基膦酸酯为中间体合成了14种新的二氯菊酰氧基膦酸酯类化合物,其结构均通过1H NMR、MS、IR确证。对合成的化合物进行了杀虫、抑菌活性测试。结果表明,在250 mg/L的浓度下,部分化合物对蚕豆蚜虫有较好的毒杀作用,在50 mg/L浓度下部分化合物有一定的抑菌活性。     

龙须藤茎皮甲醇提取物生物活性初探

龙须藤Bauhinia championii在医用方面已证实具有良好的抗菌、消炎作用,但其在农用方面的活性研究还鲜有报道。本研究分别采用菌丝生长速率法和种子生物测定法,首次测定龙须藤茎皮甲醇提取物及分离组分对6种农业有害真菌和单、双子叶两种植物的生物活性。结果表明,龙须藤甲醇浸提物对水稻稻瘟病菌Magnaporthe oryzae有一定的抑制效果,对油菜Brassica napus和稗草Echinochloa crusgalli的根芽均没有抑制作用。但其甲醇浸提物中分离的大部分组分对供试病原菌和植物的根芽都表现出一定抑制作用。杀菌活性方面:10号组分对西瓜枯萎病菌Fusarium oxysporum和番茄早疫病菌Alternaria solani的抑制效果最好,抑制率分别达到80.0%和78.0%,除草活性方面:1～3号组分对油菜根的抑制率较高,达到50%以上,2号组分对稗草根的抑制效果最好,达到68%。可见,龙须藤茎皮提取物中含有具有良好杀菌活性和除草活性的物质。     

几种植物提取物诱导马铃薯对致病疫霉的抗性

 采用纤维素膜技术研究了大蒜、洋葱、芹菜、丁香、花椒、大黄等24种植物离体组织及其提取物(其中8种中草药为水煎剂,16种其它植物为水浸剂)对马铃薯晚疫病菌(Phytophthora infestans)静止胞萌发、附着胞形成及侵入丝形成的直接影响和提取物诱导块茎对晚疫病病菌侵入机构形成的影响,并在此基础上进一步就提取物免疫处理种薯、诱导成株期抗病性、增加块茎产量的影响做了初步探讨。在洋葱、葱、大蒜等12种植物组织表面,静止胞萌发率明显低于对照(擦镜纸),而且在6种植物组织表面未见附着胞形成,10种植物组织表面未见侵入丝形成;在大蒜、韭菜等13种植物组织提取液中,静止胞萌发率明显低于对照(擦镜纸),其中6种植物组织提取液中附着胞未见形成,7种植物组织提取液中侵入丝未见形成。经8种植物组织提取物诱导处理的块茎切片,不仅保鲜期长,而且表现出较强的诱导抗性;静止胞萌发率、附着胞形成率及侵入丝形成率均明显低于对照;经8种植物组织提取物诱导处理的种薯在出芽、早期生长、抗晚疫病及产量等各方面均优于对照,病害保护率达54%、增产率达31%。     

Antimicrobial and pesticidal activity of partially purified flavonoids of Annona squamosa

Foliar extracts of Annona squamosa (Family: Annonaceae) were screened for antimicrobial and insecticidal activity against the common microbial infestants of pulses and the stored grain pest pulse beetle, Callosobruchus chinensis (Coleoptera: Bruchidae). Flavonoids isolated from aqueous extracts of A squamosa showed antimicrobial activity against all the common microbial contaminants of pulses and 80% insecticidal activity against C chinensis at a concentration of 0.07 mg ml-1. Various physico-chemical tests, chromatographic and spectroscopic studies with partially purified aqueous extract indicated the presence of flavonol type flavonoids. This may provide a useful beginning for the development of botanical pesticides for post-harvest safeguard of pulses.     

新疆夏尔希里自然保护区植物区系研究

经调查,夏尔希里自然保护区共有维管束植物81科517属1 680种(含亚种、变种),其中蕨类植物9科14属23种,裸子植物3科3属9种,被子植物69科500属1648种.对其属、种的分布区类型分析表明,北温带分布及变型和旧世界温带分布及变型的比例最大,这是由于该地区所处地理位置和植物区系的温带属性所决定的.在其他分布区...     

Antinematodal activity of some Malaysian plant extracts against the pine wood nematode,Bursaphelenchus xylophilus

Methanolic extracts of 79 Malaysian plants representing 42 families were assessed for antinematodal activity against Bursaphelenchus xylophilus using a fungal-feeding assay. Extracts of 27 plants from 19 families showed antinematodal activity, while 52 species were inactive. Five extracts (Sauropus androgynus, Eugenia polyantha, Areca catechu, Piper betle and Piper nigrum) exhibited very strong activity against Bursaphelenchus xylophilus at a minimum effective dose (MED) of 0·625 mg per ball. Strong antinematodal activity (MED: 1·25–2·5 mg per ball) was shown by the extracts of Spondias cyntherea, Codiageum variegatum, Euodia glabra and Cicca acida. Eleven extracts (Carica papaya, Ipomoea aquatica, Ocimum basilicum, Leea gigantea, Pithecellobium jiringa, Crypteronia paniculata, Myristica fragrans, Murraya koenigii, Leucaena leucocephala, Melastoma malabathricum and Morinda citrifolia) demonstrated moderate activity between MED of 5 and 10 mg per ball, and weak activity was observed in seven extracts (Ipomoea batatas, Cymbopogon citratus, Garcinia atroviridis, Psophocarpus tetragonolobus, Tamarindus indica, Allium odorum and Stenochalaena palustris). © 1997 SCI     

Inhibitors of biotin biosynthesis as potential herbicides: part 2

Isosteres and analogues of 7-keto-8-aminopelargonic acid (KAPA) and 7,8-diaminopelargonic acid (DAPA), the vitamer intermediates involved in the biosynthetic pathway of biotin, possessing chain lengths of eight carbon atoms, were prepared and evaluated as potential herbicides. The most active compounds, 7-amino-octanoic acid hydrochloride and 7-allyloxy-6-oxo-octanoic acid, displayed Arabidopsis GR50 (concentration of the active compound that causes a 50% growth inhibition) values of 5 and 10 mg kg(-1) respectively. The DAPA analog 6,7-diamino-octanoic acid dihydrochloride, when tested in the greenhouse against six weed species, displayed moderate activity against three species, being most active against foxtail millet.     

Mobility,longevity and activity of chlorfenapyr in soils treated at a termiticidal rate

BACKGROUND: The mobility, longevity and termiticidal activity of chlorfenapyr applied to soils at the termiticidal labeled rate was evaluated for 30 months after treatment (MAT) in a greenhouse study. RESULTS: There was little dissipation of chlorfenapyr in soil treated at the labeled rate for perimeter treatments for the prevention and control of termite infestations. Chlorfenapyr was detected in soil immediately below the initially treated soil in the packed soil columns. This was likely due to settling of soil. The treated soil remained toxic to subterranean termites in 3 and 7 day bioassays over the duration of the study. The treated soil displayed slow‐acting properties regarding toxicity to termites. Trace amounts of chlorfenapyr were detected in the eluates of packed soil cones. CONCLUSION: The commercial formulation of chlorfenapyr used in this study (21.45% concentrate diluted to 0.125% prior to application) killed 100% of the tested subterranean termites for at least 30 months. Copyright © 2012 Society of Chemical Industry     

Nematicidal activity of anion transport blockers against Meloidogyne incognita, Caenorhabditis elegans and Heterorhabditis bacteriophora

BACKGROUND: Because methyl bromide has been phased out as a soil sterilant, new nematicides are urgently needed. Four different chemical classes of organic acids acting as anion transport (AT) blockers were tested against a free-living nematode, Caenorhabditis elegans Maupas, a plant-parasitic nematode, Meloidogyne incognita (Kofoid and White) Chitwood, and an entomopathogenic nematode, Heterorhabditis bacteriophora Poinar, in toxicity bioassays. The materials tested were DIDS (4,4'-diisothiocyanatostilbene-2,2'-disulfonic acid), 9-AC (anthracene-9-carboxylic acid), NPPB [5-nitro-2-(3-phenylpropylamino)benzoic acid] and IAA-94 (indanyloxyacetic acid). RESULTS: All the compounds showed slowly developing nematicidal activity against second-stage juveniles of M. incognita and adults of C. elegans, but not against H. bacteriophora infective-stage juveniles. The LC(50) values of these compounds were < 50 mg L(-1) after 48 and 72 h incubation, while at 168 h incubation the LC(50) values were < 10 mg L(-1) for both sensitive species. Across both species and time, the LC(50) values generally differed no more than twofold among the four compounds tested in this study. In contrast, none of the compounds (200 mg L(-1)) caused more than control mortality to H. bacteriophora, even after 168 h of incubation. CONCLUSION: These compounds are potential leads for commercial nematicides. The insensitivity to H. bacteriophora is consistent with the natural exposure of this nematode to DST (3,5-dihydroxy-4-isopropylstilbene), a stilbene produced by its symbiotic bacterium. Based on the known activity of the compounds used in this study, it is suggested that anion transporters form the probable target sites for DIDS, 9-AC, NPPB and IAA-94 in nematodes.     

8种植物提取物对小麦白粉病病菌抑制活性研究

采用室内盆栽法,测定8种植物提取物对小麦白粉病的抑菌活性。结果表明,香樟叶、黄杨和刺槐提取物对小麦白粉病病菌(Blumeria graminis f.sp.tritici)有良好的抑制活性。其粗提物干质量浓度为40 mg/m L时,对白粉菌抑菌效果依次为57.68%,38.67%,42.39%;香樟叶粗提物对小麦白粉的室内预防和治疗作用的EC50分别为10.39 mg/m L和30.43 mg/m L,其预防效果显著优于治疗效果;测定香樟叶4种萃取物对小麦白粉病的预防效果,发现石油醚萃取物抑菌效果最好,EC50为8.71 mg/m L。说明其抑菌活性物质主要存在石油醚相中。     

Biocontrol Potential of Metchnikowia pulcherrima Strains Against Blue Mold of Apple

ABSTRACT Eight strains of Metschnikowia pulcherrima isolated over a 4-year period from an unmanaged orchard and selected for their biocontrol activity against blue mold (caused by Penicillium expansum) of apples were characterized phenotypically, genetically, and for their biocontrol potential against blue mold on apples. All strains grew well and only differed slightly in their growth in nutrient yeast dextrose broth medium at 1 degrees C after 216 h, but large differences occurred at 0 degrees C, with strain T5-A2 outgrowing other strains by more than 25% transmittance after 360 h. This strain was also one of the most resistant to diphenylamine (DPA), a postharvest antioxidant treatment. All strains required biotin for growth in minimum salt (MS) medium, although strain ST2-A10 grew slightly in MS medium containing riboflavin or folic acid, as did ST3-E1 in MS medium without vitamins. None of the strains produced killer toxins against an indicator strain of Saccharomyces cerevisiae. Analysis of Biolog data from YT plates for all eight strains using the MLCLUST program resulted in separation of the strains into one major cluster containing four strains and four scattered strains from which strain ST1-D10 was the most distant from all other strains. This was particularly apparent in 3-D and principle component analysis. Genetic differentiation of the eight strains using maximum parsimony analysis of nucleotide sequences from domain D1/D2 of nuclear large subunit (26S) ribosomal DNA resulted in detection of two clades. Strain ST1-D10 grouped with the type strain of M. pulcherrima but the remaining seven strains grouped separately, which might possibly represent a new species. All strains significantly reduced blue mold on mature Golden Delicious apples during 1 month of storage at 1 degrees C followed by 7 days at room temperature, but strains T5-A2 and T4-A2 were distinctly more effective under these conditions. Strain T5-A2 also was the most effective in tests on harvest mature apples treated with the lowest concentration of the antagonist and stored for 3 months at 0.5 degrees C. Populations of all eight strains increased in apple wounds by approximately 2 log units after 1 month at 1 degrees C followed by 5 days at 24 degrees C. Our results indicate that M. pulcherrima is an excellent candidate for biological control of postharvest diseases of pome fruit. The variation in phenotypic, genetic, and biocontrol characteristics among strains of M. pulcherrima isolated from the same orchard should make it possible to select antagonists with characteristics that are most desirable for postharvest application.     

The Synthesis and Fungicidal Activity of 2-Substituted 1-Azol-1-ylmethyl-6-arylidenecyclohexanols

A number of substituted 2,2-dimethyl-6-arylidene-1-triazol-1-ylmethylcyclohexanols and 2,2-dimethyl-6-arylidene-1-imidazol-1-ylmethylcyclohexanols were prepared from 2-methylcyclohexanone in four steps: Claisen–Schmidt condensation with substituted benzaldehydes, methylation of the resulting 2-methyl-6-benzylidenecyclohexanones, conversion to the oxiranes by interaction with dimethylsulfonium methylide and reaction of the oxiranes with triazole or imidazole. The compounds obtained were tested for antifungal activity against five phytopathogenic fungi of different taxonomic classes. EC₅₀ values were determined for all compounds. Structure–activity relationships are discussed in broad terms. Some of triazolymethyl-substituted cyclohexanols obtained are more active than triadimenol. © 1997 SCI.